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FWYNN FASHION BLOG

I Was Wrong About Ivory Suits 

The story of how I almost passed on this one.

If you had asked me a few years ago whether every man should own an ivory suit, my answer probably would have been no.

Not because I didn’t like the way they looked. Quite the opposite. I’ve always appreciated a well-executed ivory suit. I just wasn’t convinced it was practical enough to justify a place in most wardrobes. It gets dirty more easily than navy or gray, it sits well outside most men’s comfort zones, and it often feels like the kind of garment you’d wear once or twice before hanging it in the back of your closet.

As it turns out, almost none of that was true.

Today, my ivory twill suit has become one of the most versatile pieces I own. It’s a suit I reach for far more often than I ever expected, and it’s completely changed the way I think about light-colored tailoring.

It All Started In Florence

The story actually begins a few years ago during Pitti Uomo in Florence.

For that trip, I had an ivory linen suit made. I styled it tonally, packed it with the rest of my tailoring, and honestly wasn’t entirely sure how people were going to respond. An ivory suit isn’t exactly the safest choice at one of the biggest menswear gatherings in the world.

As it turned out, people loved it.

I was photographed constantly. People stopped me on the street to compliment the suit. While all of that was certainly flattering, it wasn’t what convinced me I’d stumbled onto something special.

What stayed with me was how I felt wearing it.

The suit was comfortable. It was confident. And perhaps most importantly, it kept me cool—both literally and figuratively. During the hottest days of the Italian summer, it felt effortless in a way my darker tailoring simply couldn’t.

That experience completely changed the way I thought about ivory.

Up until then, I’d viewed it as an intimidating color that required a certain type of person to pull it off. But after wearing it for several days in Florence, I realized I’d been looking at it all wrong. Ivory wasn’t a statement color at all. It was simply another neutral. And like every great neutral, it paired naturally with almost everything else in my wardrobe.

From Linen To Twill

There was just one problem: the suit was linen.

Now, don’t get me wrong—I love linen. In fact, I often say that if you’re going to wear it, you have to embrace the suck because wrinkles are simply part of the fabric’s charm. But every time I posted photos of that suit online, I knew exactly what the comments were going to be: “It wrinkles too much.” And to be fair, those comments weren’t wrong.

At the same time, my own taste in tailoring was beginning to evolve. I wasn’t moving toward oversized or baggy clothing, but I was finding myself drawn to garments with a little more ease, drape, and movement. I still wanted elegant tailoring, but I also wanted it to feel relaxed.

That got me thinking. What if I could capture everything I loved about that ivory linen suit without quite so much wrinkling? That question eventually led me to this ivory twill. It has the same versatility and lightness that made the linen suit such a favorite, but in a fabric that feels a little cleaner and a little easier to live with.

The Biggest Surprise

The biggest surprise wasn’t how the suit looked.

It was how often I wore it.

When I first had it made, I assumed it would be reserved for summer weddings, vacations, and perhaps another trip to Pitti Uomo. In my mind, it had a very specific purpose. It certainly wasn’t going to become one of my regular rotation pieces.

Instead, the exact opposite happened.

The more I wore it, the more I realized I’d been thinking about ivory all wrong. Once I stopped treating it like a statement color and started treating it like a neutral, everything else fell into place.

It works beautifully with every shade of brown. It pairs effortlessly with blue, olive, burgundy, and even black. Rather than limiting my options, it actually opened up combinations that felt completely different from anything I could create with a navy or gray suit.

Then there were the trousers.

When I designed the suit, I intentionally included belt loops because I knew I’d wear the trousers separately from time to time. What I didn’t anticipate was just how often I’d reach for them. They’ve quietly become one of the hardest-working pairs of trousers in my wardrobe, and that was the moment I realized this wasn’t simply a great suit. It was two incredibly versatile garments that each earned their place on their own.

5 Ways I Style An Ivory Suit

One of the reasons this suit has become such a staple is that it adapts to so many different situations. Here are five of my favorite ways to wear it.

01

Funky Tie

One of the styling principles I talk about most often is the importance of having a single focal point. If you want one piece of an outfit to stand out, everything else has to support it.

That’s exactly what’s happening here.

The colorful patterned tie immediately becomes the center of attention because the ivory suit provides such a clean, understated foundation. Nothing else competes for your eye. Instead, the suit allows the tie to do exactly what a true statement piece is supposed to do: make the statement.

02

Hollywood Chic

This is probably the simplest outfit in the collection, and I think that’s exactly why it works.

Everything feels tonal and intentional. The only real point of contrast comes from wearing the shirt collar over the lapels—a not-so-subtle nod to 1970s styling that also serves a practical purpose.

When you’re wearing a suit without a tie, that simple detail adds just enough structure and visual interest to make the outfit feel complete.

Sometimes it’s the smallest styling decisions that make the biggest difference.

03

Summer Wedding

Although an ivory suit naturally lends itself to casual styling, it can absolutely be dressed up.

The key is choosing pieces that complement its personality rather than trying to force it into looking like a traditional business suit.

A microstripe shirt and knit tie add polish without feeling overly formal, while black shoes and a black belt reinforce the dressier nature of the outfit.

The result is refined enough for a summer wedding while still feeling appropriate for the relaxed character of the suit.

04

Vacation Mode

If you’re headed somewhere warm, this is where I’d have a little more fun.

A patterned shirt immediately funkifies the outfit and gives it an entirely different personality. Swapping loafers for leather sandals relaxes the look another notch, making it feel perfectly at home walking through a beach town, heading to dinner at a resort, or enjoying a cocktail as the sun goes down.

One of the biggest misconceptions about an ivory suit is that it’s precious.

I don’t see it that way at all.

I think it’s meant to be lived in.

05

Pants Separate

One of the biggest surprises about this suit has nothing to do with the jacket.

It’s the trousers.

Paired with our Merlot Bamboo Sport Coat, they become the foundation of an entirely different outfit. The rich color of the jacket adds visual interest, while the tank top keeps everything cool and comfortable during the hottest days of summer.

Every year I get asked how to stay cool without sacrificing style.

This is one of my favorite answers.

More importantly, it’s proof that the value of this suit extends well beyond wearing it as a matching set. The trousers have become one of the most versatile separates I own.

The Bottom Line

When I almost decided not to make this suit, I thought I was making the practical decision.

Stick with navy. Stick with gray. Play it safe.

What I didn’t realize was that sometimes the pieces you hesitate over become the ones you end up loving the most.

This ivory suit has reminded me that the best additions to your wardrobe aren’t always the ones that make the most sense on paper. They’re the ones that quietly become part of your life—the garments you reach for again and again because they simply work.

After more than fifteen years of building my wardrobe, that’s become the clearest sign that a piece truly belongs.

Thanks, as always, for reading.

Why Every Man Still Needs A Navy Blazer 

Over the past 15 years, I’ve owned a lot of clothes.

Some of them I was excited about for a few months before they quietly disappeared from my rotation. Others looked great but, for one reason or another, I just never found myself reaching for them.

But every once in a while, a piece earns a permanent place in my wardrobe.

For me, this navy hopsack sport coat is one of those pieces.

If you’ve followed He Spoke Style for any length of time, you know that I’m not someone who believes every man needs unlimited options. In fact, over the years I’ve come to appreciate the opposite. I’d much rather own fewer, high-quality pieces that I genuinely enjoy wearing than a wardrobe full of clothes that spend most of their lives on a hanger.

When I designed this navy hopsack sport coat for the He Spoke Style Shop, I wasn’t trying to reinvent anything or chase the latest trend. I simply wanted to create the jacket I hoped I’d reach for more than any other. Looking back, I’d say that’s exactly what happened.

Today, I want to explain why—and show you five ways I’ve been wearing it recently.

Why This Jacket?

Every detail of this jacket reflects something I’ve learned over the past 15 years of building my wardrobe.

I chose a true navy because it works with virtually everything else I own without ever feeling too bright or too dark. The hopsack weave provides enough texture to feel relaxed and approachable while remaining refined enough to wear with a dress shirt and tie. A softer construction allows the jacket to move naturally instead of feeling stiff or overly formal, and patch pockets reinforce its casual versatility.

None of those decisions were accidental.

I wasn’t trying to create another navy sport coat. I was trying to create the navy sport coat—the one I’d instinctively reach for whether I was heading to a meeting, traveling, going out to dinner, or simply getting dressed without wanting to overthink it.

What Surprised Me

What I didn’t expect was just how completely this jacket would take over my wardrobe.

Somewhere along the way, I realized that whenever I had to get dressed and wasn’t quite sure what to wear, I instinctively reached for this jacket. It wasn’t because I was forcing myself to wear it or because I wanted to showcase it. I wore it because it simply worked.

That realization taught me something that has fundamentally changed the way I think about building a wardrobe. The best pieces aren’t necessarily the ones that get the most compliments or attract the most attention. More often than not, they’re the garments that quietly make getting dressed easier. They’re dependable, versatile, and they continue to earn their place through years of wear rather than a few weeks of excitement.

Why It Earned Its Place

Looking back, I think there are three reasons this jacket has remained one of the hardest-working pieces in my wardrobe.

The first is that it solves more problems than just about any other tailored jacket I own. There are jackets that are dressier, jackets that are more casual, and certainly jackets that are more interesting. But very few move as comfortably between a business meeting, dinner, travel, a weekend date, or multiple seasons without ever feeling out of place.

I didn’t come to that conclusion because someone told me a navy sport coat was versatile. I came to it because, year after year, I kept finding reasons to wear this one. Experience taught me what advice never could.

The second reason is that it makes everything else in my wardrobe easier to style.

It took me a while to appreciate this, but eventually I realized I wasn’t building outfits around the jacket at all. Instead, the jacket made everything else work together. Whether I paired it with gray trousers, white linen, khaki cotton, denim, striped shirts, Oxford cloth, knit polos, ties, or pocket squares, it always felt like a natural fit. Over time, it became the glue that tied my wardrobe together rather than the centerpiece demanding attention.

It makes everything else in my wardrobe easier to style.

The third reason took the longest to understand.

For years I knew I preferred wearing this jacket over the more traditional navy blazers I’d owned in the past, but I couldn’t quite explain why. Eventually, it clicked.

It was the hopsack fabric.

The open weave gives the jacket texture and visual depth that immediately makes it feel more relaxed than a smooth worsted blazer. At the same time, it’s still refined enough to wear with tailored trousers, a dress shirt, and a tie. Finding that balance isn’t easy, but when you do, you end up with a jacket that’s equally comfortable dressed up or dressed down.

I think that’s the real reason this jacket has stood the test of time.

5 Ways I Wear It

01

The Classic

If someone asked me to picture a timeless sport coat outfit, this would probably be it: a navy sport coat, gray trousers, a pale blue shirt, and a patterned tie.

What’s interesting is that I didn’t arrive at this combination because someone told me navy and gray worked well together. I arrived here because I kept wearing it. Whether it was a meeting, an event, or simply a day when I wanted to feel put together, this outfit never let me down.

Some combinations become classics because they simply continue to prove themselves over time. This is one of them.

02

Easy Summer Style

This is where the jacket really starts to surprise people.

Many men assume a navy sport coat belongs with darker trousers and more formal outfits, but pairing it with white linen trousers completely changes its personality. The result feels lighter, more relaxed, and perfectly suited to warm weather.

The hopsack weave plays a big role here as well. Because the fabric already has a casual texture, the jacket feels completely natural in a summer outfit instead of looking like a business jacket that’s been pressed into weekend duty.

It’s a combination I come back to every summer because it never feels like I’m trying too hard.

03

The Travel Jacket

Travel is one of those situations where comfort has become an excuse to look like a complete slob. I understand wanting to be comfortable, but I don’t think comfort and style have to be mutually exclusive.

Here, the knit polo and jeans are comfortable enough for a flight or train ride, while the hopsack sport coat makes the outfit look considerably more polished without feeling overly formal or restrictive.

One thing I’ve learned over the years is that when you look put together, you tend to carry yourself a little differently. After spending enough time in airports and train stations, I’d much rather be slightly overdressed than feel like I gave up before the trip even started.

04

Simple Date Night

For dinner with friends or a date night, this is probably where I land most often.

A classic Oxford cloth shirt, khaki wool trousers, and brown shoes aren’t particularly bold choices—and I think that’s exactly why they work.

The older I’ve gotten, the less interested I’ve become in outfits that try too hard. I’d much rather wear something that feels confident, understated, and completely natural. For me, this outfit strikes that balance perfectly.

05

With Jeans

One of the questions I get asked more than almost any other is whether a sport coat can be worn with jeans.

Absolutely.

The trick isn’t really the denim. It’s making sure everything else feels equally relaxed. A block stripe shirt, suede loafers, a suede belt, and a textured hopsack sport coat all work together because nothing feels overly formal.

The result is an outfit that looks intentional rather than looking like you accidentally paired a suit jacket with jeans. It’s another combination I find myself returning to because it simply works.

The Bottom Line

When I first started building my wardrobe, I was always chasing the next thing. The next suit. The next jacket. The next pair of shoes. Like most people who become interested in classic menswear, I assumed building a better wardrobe meant constantly adding to it.

These days, I think very differently.

Experience has taught me that the clothes I value most aren’t the ones that demand attention. They’re the quiet, dependable staples that consistently make getting dressed easier and always seem to look right, regardless of the occasion.

That’s exactly what this navy hopsack sport coat has become for me. After all this time, it has more than earned its permanent place in my wardrobe—not because it’s the flashiest jacket I own, but because it’s the one I continue to reach for without thinking.

And that’s why I believe every man should own one.

Thanks, as always, for reading.

Why You Look Bad In Suits 

And how to fix it.

If you’ve ever put on a suit and thought, “Why doesn’t this look right?”—you’re not alone.

Most men assume the issue is obvious. The suit doesn’t fit. It’s too big, too tight, or poorly made. And while fit certainly matters, it’s rarely the only problem—and often not even the primary one.

In reality, the difference between a suit that looks good and one that feels slightly off usually comes down to a series of smaller details. Individually, they may seem insignificant. But together, they shape how the entire outfit is perceived.

Understanding those details—and how they interact—is what separates a suit that simply exists from one that actually works and looks great.

1. You Don’t Know How to Wear a Suit

This may sound incredibly basic, but it’s one of the most common issues—and one of the easiest to overlook.

Wearing a suit well involves a set of small conventions that, when ignored, subtly undermine the entire look. Buttoning the bottom button of a jacket, wearing a tie that’s too long or too short, failing to show any shirt cuff, or keeping your jacket buttoned while sitting—none of these are catastrophic mistakes on their own. But they signal a lack of familiarity, and that affects how the suit is read.

A well-worn suit looks natural. It doesn’t feel like a costume or something you’re trying to “get right.” Getting these small details in order immediately brings a sense of harmony and balance to the entire outfit.

2. Your Outfit Is Fighting Itself

A suit doesn’t exist in isolation. Everything you pair with it—shirt, tie, shoes—either reinforces the look or works against it.

Problems tend to arise when these elements don’t align. A wide tie paired with narrow lapels, a highly formal suit worn with a casual shirt, or multiple bold elements competing for attention can all create a kind of visual tension that feels unresolved.

What’s important to understand is that nothing in these combinations is necessarily wrong on its own. The issue is how the pieces interact. When they don’t feel like they belong together, the result is an outfit that lacks cohesion.

A strong look feels intentional. The individual elements support each other rather than compete against each other.

3. You’re Ignoring Proportions

Even when a suit technically fits, it can still look wrong.

This is where proportion comes into play—how the different elements of the suit relate to your body and to each other. Jacket length, lapel width, button stance, and trouser rise all contribute to the overall balance of the silhouette.

When these proportions are off, the effect is subtle but noticeable. A jacket that’s slightly too short can throw off the entire line. Lapels that are too narrow or too wide for your build can make the suit feel out of sync with your frame. Trousers that sit too low can disrupt the relationship between the jacket and the rest of the outfit.

You may not immediately be able to identify the issue, but you’ll register that something doesn’t look quite right. That’s proportion at work.

4. Your Posture and Body Language Are Off

A suit doesn’t create presence—it amplifies it.

If you’re standing stiffly, slouching, or moving in a way that suggests discomfort, the suit will make that more apparent. This is why two people wearing the exact same suit can look entirely different. The difference often has less to do with the clothing itself and more to do with how it’s worn.

A relaxed, upright posture and natural movement go a long way toward making a suit look right. The goal isn’t to “perform” confidence, but to remove the tension that makes the suit feel unnatural.

5. You’re Trying Too Hard

There’s a point where attention to detail becomes counterproductive.

Too many accessories, too many statement pieces, or too many attempts to “elevate” the outfit can make it feel forced. A suit already has structure and presence—it doesn’t need to be overloaded.

This is a common phase, especially when you start to take an interest in style. There’s a tendency to add more, to make the effort visible. You do this because you feel the need to show people you are “into” style. Over time, though, you realize that restraint is what makes an outfit feel effortless.

A well-considered suit doesn’t draw attention to individual elements. It reads as a whole.

6. Your Grooming Is Undermining Everything

The suit is only part of the equation.

Wrinkled shirts, unpolished shoes, unkempt hair, or neglected details can quietly bring down an otherwise solid outfit. People don’t evaluate your clothing piece by piece—they take in the overall presentation.

If something feels off, it’s often because one of these supporting elements isn’t in place. A suit can elevate your appearance, but it can’t compensate for a lack of attention elsewhere.

What About Fit?

At this point, it’s worth addressing fit directly.

It absolutely does matter—a great deal. But it’s also where most people focus first, and often exclusively. As a result, they overlook everything else.

A suit can fit well and still look off if the surrounding elements aren’t working. At the same time, once everything else is in place, proper fit is what sharpens the entire look.

The key is understanding that fit isn’t just about size. It’s about specific details—shoulders, sleeve length, jacket length, trouser break—and how they come together.

If you want a deeper breakdown of how a suit should actually fit, that’s a separate conversation entirely and one that we’ve got a complete guide for.

The Bottom Line

Looking good in a suit isn’t about getting one thing right. It’s about how everything works together.

  • The way you wear it.
  • How the pieces interact.
  • How it fits your body.
  • And how much restraint you exercise.

When those elements align, the difference is immediate. And more importantly, it doesn’t feel forced.

Thanks, as always, for reading.

10 Menswear Truths Most Men Learn Too Late 

Most men have been taught the wrong things about style.

Not deliberately, but gradually. Over time, certain ideas take hold: that dressing well is about money, brands, or keeping up with trends.

But after more than a decade working in menswear, I’ve found that many of these beliefs don’t hold up in practice. The things men tend to focus on are often the least important, while the details that actually shape how an outfit looks are frequently overlooked.

What follows are 10 observations that have consistently proven true—and that have shaped how I think about dressing well.

1. Expensive Clothes Don’t Make You Stylish

There’s a persistent belief that spending more will naturally result in looking better. It’s understandable, but it rarely plays out that way.

I’ve seen expensive outfits that feel disjointed, alongside much simpler combinations that look far more considered. The difference usually has little to do with price and much more to do with how the clothing fits and sits on the body.

Without that foundation, even high-end clothing struggles to look right. With it, simpler pieces can feel refined and complete.

Most Modern Jackets Are Too Short

Over the past decade, jacket lengths have steadily shortened. While that can look sharp at first glance, it often disrupts the overall balance of an outfit.

A shorter jacket compresses the torso and throws off the visual relationship between the upper and lower body. Traditionally, jackets were cut slightly longer—not as a stylistic choice, but to create a more natural sense of balance.

When that balance is right, everything else tends to fall into place.

3. The Best Wardrobes Are Usually Small

It’s easy to assume that more options lead to better style. In reality, the opposite is often true.

Most well-dressed men rely on a relatively small set of pieces that work well together. They know what fits them, what suits their lifestyle, and what they feel comfortable wearing.

It’s not about having more—it’s about having the right things, and wearing them consistently.

4. Tailoring Matters More Than Brands

A lot of attention is placed on labels—where something was made, who designed it, how much it costs.

But what actually makes the biggest difference is how it fits.

Even a well-made garment won’t look right if the fit is off. And on the other hand, something simple can look excellent when it’s properly tailored.

Over time, this becomes very clear. Fit is where style begins.

5. Great Wardrobes Start With Neutral Colors

There’s a tendency to build a wardrobe around statement pieces or bold colors. But what tends to work best is a foundation of neutral tones.

Navy, grey, brown, and ivory naturally work well together. They create consistency and make getting dressed much easier.

Once that foundation is in place, variation becomes more intentional—and more effective.

Trends are temporary by nature. They come and go, often quickly.

When a wardrobe is built around them, it tends to reflect a very specific moment in time—and can feel outdated just as quickly.

Clothing rooted in classic design tends to last much longer. It evolves more slowly, and as a result, ages far more gracefully.

7. Shoes Anchor the Entire Outfit

Shoes are often overlooked, but they have a disproportionate impact on how an outfit is perceived.

A strong pair can elevate something simple, while a poor choice can undermine an otherwise well-put-together look.

They ground the outfit. And over time, you start to notice just how much they matter.

8. The Best Outfits Are Usually the Simplest

There’s a tendency to add more—more layers, more detail, more variation—in an effort to make an outfit more interesting.

But often, the opposite is true.

Simpler combinations tend to feel more refined and more intentional. There’s a clarity to them that gets lost when too many elements compete for attention.

Restraint, more often than not, is what creates elegance.

9. Most Style Problems Are Fit Problems

When something doesn’t look right, it’s often blamed on the garment itself—the brand, the style, or the trend.

But more often than not, the issue is simply fit.

Too tight, too loose, too short, too long—small differences can completely change how something looks.

When the fit is right, everything else becomes much easier.

10. The Best Style Is Personal

It’s easy to look outward—at trends, brands, and what other people are wearing.

But over time, what matters more is understanding what works for you.

Your lifestyle, your preferences, and your environment all play a role. When your clothing reflects that, it feels more natural and more consistent.

Style isn’t about following a formula. It’s about understanding yourself—and dressing in a way that aligns with that.

The Bottom Line

Menswear isn’t about rules. And it’s not about buying more. It’s about understanding a few core principles—and applying them consistently.

Because the goal isn’t to follow fashion. It’s to develop a sense of style that actually lasts.

Thanks, as always, for reading.

11 Last-Minute (But First-Class) Gift Ideas 

Life is busy, but it’s never been easier to find and deliver those last-minute gifts. 

Knowing your time is tight, here are ten quick ideas to help you find something special for that special someone . . . in a hurry. And since we know you’re in such a hurry, we’re going to dispense with the lengthy intro. Like, what do you really need to know?!

01

Temperature Control Smart Mug

The Ember Temperature Control Smart Mug makes a great gift for the coffee or tea enthusiast. One of life’s most disappointing moments is coming back to a cup of coffee and finding you missed that temperature sweet spot. With a sleek design and connected app, Ember provides full control over your drink’s warmth, ensuring no more lukewarm sips. It’s a thoughtful gift for busy professionals, coffee enthusiasts or anyone who enjoys their hot drinks just so.

02

Black Truffle Infused Olive Oil

Like cilantro, TRUFF can be a “love it or hate it” item for food lovers, but that’s part of what makes it a fun gift. Cold-pressed olive oil is infused with the rich, earthy flavor of black truffles to make an interesting finishing oil perfect for drizzling over salads, pasta or roasted vegetables. Considering packaging with TRUFF’s hot sauce if you’re looking to give a bit more.

03

4 Piece Cocktail Kit Gift Set

The 4 Piece Cocktail Kit Gift Set, also known as the Prohibition Set, is the perfect gift for cocktail enthusiasts who appreciate the classics. Just add alcohol to craft Old Fashioneds, Champagne Cocktails, Manhattans and Sazeracs. Each kit comes complete with both ingredients and any necessary tools. TSA friendly, these are easy to carry for a bachelor party or weekend away. 

04

Clip 4 Portable Mini Bluetooth Speaker

Get 10 hours of playback time with this portable, yet powerful, Bluetooth speaker from JBL. Always handy for pool parties, beach trips, backyard barbecues or any number of gatherings, set the right vibe without carrying a large speaker. There are a million speakers to choose from, but JBL is a brand you can always trust. 

05

Portable Charger Power Bank

A portable power bank is a thoughtful gift for anyone who’s always on the go. Compact yet powerful, this power bank from Zendure provides multiple charges for phones, tablets and other gadgets without needing a wall outlet. It’s a practical, thoughtful gift offering peace of mind and convenience for the traveler or commuter. Not sure if they might already have one? Don’t worry as having an extra at the office or in the daily bag always comes in handy.

06

-30°F Winter Touchscreen Gloves

Removing gloves to send a quick text is annoying at best, miserable at worst. Cevapro’s -30°F Winter Touchscreen Gloves solve this problem. Great for anyone braving a cold city commute, cool hike or outdoor winter work, the built-in touchscreen-compatibility will keep your fingers safe from Jack Frost.

07

Da Vinci Code Mini Cryptex Lock Puzzle

This gift idea is a bit different. Inspired by “The Da Vinci Code,” Shashibo’s combination lock box is a fun way to enclose another gift or hide something fun. The code is programmable and, with 308,915,776 combinations, be sure that you write it down!

08

Hinoki Fantôme

Candles make great gifts and the Hinoki Fantôme candle is a luxurious, woodsy scent experience, perfect for both men and women. Inspired by the calming aromas of Japanese hinoki wood, this candle carries notes of smoked leather, hinoki cypress, and moss. Hand crafted in Los Angeles by Boy Smells, this candle’s 50-hour burn is a welcome addition to any home. 

09

Pile Lined Hardsole Slipper

The Minnetonka Men’s Pile Lined Hardsole Slippers combines warmth, comfort and durability with classic style. With plush pile lining, these slippers provide a cozy, cushioned feel ideal for lounging at home while maintaining sturdy soles necessary for quick trips outside or to the garage. Made from sturdy suede with a classic moccasin design, they offer timeless appeal and long-lasting wear. Channel your inner upper Midwest with these tried-and-true favorites.

10

He Spoke Style Gift Card

Can’t wait even a day for delivery? The He Spoke Style Gift Card can be delivered practically instantly! Buying clothes for someone is always a challenge, but a gift card is an easy way to help a loved one add something new to their wardrobe. We, of course, believe anything from our shop is likely to become one of their favorite pieces as well.

11

Stay Tailored Hat

Born from my iconic YouTube sign-off, our “Stay Tailored” baseball cap embodies the values and creed of the world of He Spoke Style – approachable, relatable, classic but modern. In addition to making tailoring a little less stuffy, our signature ball cap also makes it more approachable and adds an element of sportiness to what can sometimes feel too formal.

The Bottom Line

Thanks for reading, but you don’t have any more time to spare! May the delivery times be ever in your favor.

I Found The Perfect Navy Blazer Alternative 

When a blazer feels too formal and t-shirt too casual, there’s one garment that bridges the gap perfectly: the navy chore coat.

Finding the right balance between elevated and casual can be tricky. We’ve all been there – standing in front of the mirror, trying on sport coat after sport coat, only to feel overdressed for the occasion. A navy blazer? Too formal. That houndstooth sport coat? Too much. The madras jacket? Definitely not right for a casual date or everyday wear.

The struggle is real: you want to elevate your outfit without looking like you’re trying too hard. While blazers and sport coats have their place, sometimes they’re simply overkill for casual dates, flexible workplaces, or even just regular old day-to-day style.

Enter the chore coat – quite possibly the best alternative to a sport coat for the modern man who wants to dress well without overdoing it.

The History of the Chore Coat: A 150-Year Style Legacy

Understanding the history of what we wear adds depth to our style choices. The chore coat has a fascinating origin story that explains why it works so well today.

Created in 19th-century France, the chore coat was originally designed for laborers, railroad workers, and farmers who needed something tough but lightweight to throw over their work clothes. These early versions were made from durable cotton drill with four large pockets to keep tools handy – function over fashion was the name of the game.

Vintage photo of men wearing chore coats

A vintage photo of French workers wearing their blue de travail uniform (image via)

The traditional color was blue, and some historians believe this is actually where the term “blue collar” originated. After World War II, the chore coat gained popularity in Japan and eventually made its way into mainstream menswear, but the core design has remained remarkably unchanged.

What makes the chore coat special is that we’re wearing a garment that’s been proven for over 150 years. It’s not a trend – it’s a classic piece of menswear that still looks good today while maintaining its practical and utilitarian roots.

4 Key Benefits of Choosing a Chore Coat Over a Sport Coat

While comparing a chore coat to a sport coat is somewhat like comparing apples to oranges, there are distinct advantages to choosing the chore coat as your go-to elevated casual layer.

1. All-Day Comfort

The lightweight, unstructured design of a chore coat gives you full range of motion. Made from breathable cotton twill, you’ll practically forget you’re wearing it – perfect for long days when a more structured blazer might feel restrictive.

2. Ultimate Travel Companion

A chore coat is one of the best travel jackets available. It’s extremely lightweight and easy to pack, but where it really shines is as a practical travel layer. Keys in one pocket, passport in another, phone easily accessible, and wallet safely tucked inside – it’s functional style at its finest.

3. Seasonal Versatility

Made from lightweight cotton twill, our navy chore coat works from spring through fall. It’s perfect for layering when it’s cold, ideal for seasonal transitions, and during the summer, when you’re moving between air-conditioned spaces, it can be the difference between shivering and feeling comfortable.

4. Practical Functionality

Those four pockets aren’t just for show – they’re there for a reason. Don’t be precious about using them. The chore coat’s practical design makes it perfect for carrying essentials while maintaining a polished appearance.

5 Ways to Style Your Navy Chore Coat

The beauty of a navy chore coat lies in its versatility. Here are five distinct looks that showcase its range.

01

Modern Casual Chic

This look is quite possibly the ultimate summer date night outfit, striking the perfect balance between modern, casual, and chic. The foundation starts with our medium gray cotton pique button-up paired with our crisp white cotton trousers, creating a light and neutral base that’s perfect for warmer weather. Yes, wearing white trousers can feel like a high-wire act, but the key is simply not being a slob about it (N.B. that’s sarcasm.)

The navy chore coat provides beautiful contrast against this light foundation, while black leather accessories add sophisticated touches without being too formal. A black leather belt and black leather loafers ground the look, and classic sunglasses complete the ensemble.

02

The “Too Easy”

This combination is literally “too easy” to put together, which is exactly why it works so well for busy mornings or when you want to look put-together without much effort. Begin with timeless menswear staples: our light blue Oxford cloth button-down combined with stone cotton trousers. Normally this pairing would call for a navy sport coat if you wanted a very classic menswear ensemble, but swapping in the chore coat creates an entirely different look and feel.

What makes this outfit shine is its classic simplicity, enhanced by brown leather accessories that add warmth and sophistication. Brown suede pieces work particularly well here, creating a cohesive look that feels both polished and approachable. The chore coat transforms what could be a predictable combination into something fresh and contemporary while maintaining the timeless appeal of classic menswear.

03

Tonal Sharp Casual

Here’s where the power of tonal dressing really shines, offering a sharp casual edge that’s perfect when you want to wear light-colored jeans but need to dress them up just a bit. Start with a navy blue cotton pique shirt with light wash denim to create a slightly more sophisticated take on the classic jeans-and-shirt combination. Cotton pique shirts are an excellent middle ground between t-shirts and dress shirts on the formality spectrum.

Layer the navy chore coat over the navy shirt for tonal sophistication that elevates the entire look without being too matchy-matchy. The monochromatic palette gets broken up by black leather accessories and minimal white leather sneakers, keeping everything feeling modern and approachable.

This particular combination proves that you can dress up jeans significantly while maintaining a casual, comfortable vibe that works for dates, casual nights out, or any situation where you want to look sharp but not stuffy.

04

The Preppy One

Classic prep gets a modern twist that makes it feel fresh and contemporary rather than costume-like. We’re starting with some preppy staples like khaki cotton trousers and a denim dress shirt, but letting the navy chore coat replace the expected navy sport coat to provide the modern element that sets this look apart from traditional preppy uniforms.

Consider adding a green striped tie for full preppy effect, though it’s easily removed for a more casual appearance. Brown leather accessories maintain the aesthetic – penny loafers and a brown leather belt create that classic preppy sophistication, while the chore coat keeps the overall feel relaxed and contemporary. This look is perfect for those who appreciate preppy style but want to avoid looking like they’re trying too hard or stuck in the past.

05

Elevated Casual

This outfit is specifically designed for those who want to see how a chore coat can elevate truly casual pieces into something more sophisticated. The foundation is built on casual wardrobe staples: a classic Oxford cloth button-down paired with dark denim. This is the type of combination that could easily look too casual on its own, but the chore coat transforms it into something suitable for a wider range of occasions.

The key to making this elevated casual look work is paying attention to the details, particularly the quality of your accessories. A well-made leather belt and quality leather Chelsea boots anchor the outfit and provide the elevated touches that make all the difference. The chore coat serves as the perfect bridge between the casual foundation and the more refined accessories, creating a look that’s comfortable enough for everyday wear but polished enough for casual social occasions.

Navy Chore Coat vs. Blazer: Making the Right Choice

Choose a chore coat when:

  • You want to elevate a casual outfit without looking overdressed
  • You need something comfortable for all-day wear
  • You’re traveling and want a versatile, packable layer
  • The occasion calls for smart-casual rather than business casual

Choose a blazer when:

  • You need to dress for business or formal occasions
  • You want a more structured, tailored silhouette
  • You’re attending events where traditional menswear is expected

The Bottom Line: Why Every Man Needs a Navy Chore Coat

In a world where we’re constantly navigating between casual and formal, the navy chore coat offers the perfect middle ground. It’s a garment with over 150 years of proven design, offering comfort, versatility, and style in one package.

Whether you’re heading out for a casual date, running weekend errands, or simply want to elevate your everyday style without the formality of a blazer, a navy chore coat is an investment piece that will serve you well across seasons and occasions.

The chore coat isn’t trying to replace your blazer – it’s filling a gap in your wardrobe that you might not have realized existed. It’s the perfect solution for those moments when you want to look put-together without looking like you’re trying too hard.

Ready to add this versatile piece to your wardrobe? A quality navy chore coat is one of the best investments you can make in your casual-to-elevated style game. (And, pssst . . . we beat Todd Snyder on pricing…)

Thanks, as always, for reading.

My Premium Every Day Carry For 2025 

Today, I’m excited to share my premium everyday carry items for 2025 – the carefully curated collection of items I rely on daily. But before we dive in, let me set some expectations.

First, if you’re looking for traditional EDC gear like tactical knives, multitools, carabiners, or machined card cases with RFID blocking, this isn’t that kind of list. That’s simply not my style.

Second, I want to be completely transparent: everything I’m featuring here was purchased with my own money. There’s no sponsored content or “influencer” nonsense going on – these are genuine recommendations based on my personal experience.

With that said, let’s explore my 10 essential items (plus a couple of bonuses) that make up my premium daily carry.

01

Bennett Winch Briefcase

The foundation of my daily carry is my Bennett Winch briefcase, which houses most of these items. I’ve been a fan of this British brand since they launched in 2014, and their combination of quality and style is unmatched.

It’s constructed from waterproof cotton canvas with full-grain leather trim and handles, plus solid brass hardware that speaks to its premium build quality. Despite its slim profile, it’s surprisingly spacious inside with a padded laptop sleeve that accommodates up to 16-inch laptops, three large internal pockets, and dedicated slots for pens.

The external zippered pocket is perfect for items I need quick access to, like my wallet, phone, or keys. There’s also a clever leather panel on the back that slips over suitcase handles for easy travel, and it includes a removable shoulder strap for when I need it.

I chose the black version for its versatility with my personal style, though it comes in several colorways. The thoughtful design makes it perfect for both professional settings and travel.

02

Goyard Card Case

Rather than carrying a traditional wallet, I’ve streamlined to a Goyard card case in their classic design and most iconic colorway. This piece has been with me for about a decade, and while the leather edges show significant wear, the integrity remains intact.

The patina and wear actually add character to the piece – it tells the story of a well-loved accessory that’s been through countless adventures. Despite its age, it continues to function perfectly and remains one of my most reliable everyday items.

03

Montblanc Meisterstück

I carry two pens, but only when I have my briefcase – otherwise, it’s just one (I’m particular, not obsessive).

This bordeaux-colored ballpoint has been my companion throughout my entire Army career. Like a fine wine, it has aged beautifully, save for one crack from an unfortunate drop that still makes me wince. The pen became somewhat legendary among my colleagues, and for good reason – it feels incredible in hand and writes with Greek Blue ink that’s both professional and distinctive.

04

S.T. Dupont Line D Gold Dust Pen

This was my retirement gift to myself after over 20 years of active Army service. This rollerball pen was exclusive to the US market, and I managed to snag the very last one. The actual gold flakes suspended in the lacquer make each pen unique, and while it might seem obnoxious, it’s undeniably beautiful. The weight and balance are perfect, and the satisfying click of the cap is pure ST Dupont craftsmanship.

05

Jacques Marie Mage Fitzgerald Sunglasses

These sunglasses pay tribute to President John F. Kennedy, who famously wore American Optical Saratoga frames. While these aren’t those exact glasses, the Fitzgerald model captures that classic shape with a modern sensibility through lighter lenses.

The quality is immediately apparent when you hold them – these are substantial, well-crafted pieces that justify their reputation. Unfortunately, they’re no longer available in stores (these are number 60 of 400), but you might find a pair on the secondary market.

For those curious about Jacques Marie Mage and whether they’re worth the investment, check out the comprehensive review right here on HSS – it’s the most thorough analysis of the brand you’ll find anywhere.

06

iPhone 16 Pro

Let’s address the obvious: my iPhone 16 Pro in Desert Titanium. I upgraded from the 14 Pro primarily due to battery degradation, and with upcoming travel to Florence, I didn’t want to constantly carry external batteries.

While I typically choose black, I decided to try something different with the Desert Titanium finish. The case is a basic Belkin from the Apple Store – functional but admittedly uninspiring. If you have recommendations for more stylish iPhone cases, I’m all ears.

07

Moscot Lemtosh Reading Glasses

Age brings wisdom and, apparently, the need for reading glasses – which have been completely life-changing. My choice: Moscot Lemtosh frames in brown ash, size 46.

I’m a longtime fan of the Lemtosh model and own several pairs as sunglasses. While some dismiss them as Julius Tart Arnel knockoffs, I disagree. Honestly, though, these specific frames were chosen because Robert Downey Jr. wore them in Oppenheimer. If you’re going to need reading glasses, why not channel some of that RDJ coolness?

08

Porsche Cayenne Key

The key to my favorite vehicle I’ve ever owned (aside from my first car, a 1989 Ford Mustang hatchback): my 2019 Porsche Cayenne in Mahogany.

I was a devoted BMW driver for years, starting with a basic 328 with manual transmission and no options, then upgrading to a 535xi that I absolutely loved. However, by the time I needed something new, BMW’s design direction had lost its appeal, and Porsche had succeeded in seducing me.

Side note: If you haven’t listened to the Porsche episode of the Acquired podcast, it’s absolutely fascinating.

I bought this base-model Cayenne certified pre-owned with very low miles. It represents the perfect combination of power, performance, agility, design, style, elegance, and luxury. I couldn’t be happier with it and hope I won’t need a replacement anytime soon.

09

A. Lange & Söhne Lange 1

For those who’ve been asking about watch content, while I don’t plan to do dedicated watch videos anymore, I can’t ignore what’s on my wrist: my Lange 1 in pink gold.

This watch is simply extraordinary. The dial features one of the most unique, gorgeous, and iconic designs in horology. At 38.5mm, the size is perfect, and its versatility makes it suitable for virtually my entire wardrobe (though I’d need a black strap for formal occasions).

What I particularly appreciate about Lange is their understated presence in the watch world. They embody that “if you know, you know” philosophy that I find appealing.

10

AirPods Max

These aren’t exactly “if you know, you know” – my AirPods Max in Starlight are quite mainstream. But they’ve earned their place in my daily carry.

While I also own AirPods Pro, they don’t stay in my ears well, compromising the noise cancellation. The AirPods Max, however, are game-changing for travel, especially on planes. At home, they live on a dedicated stand, and for travel, they go in a protective case.

The sound quality and noise cancellation make them indispensable for both work and leisure.

The Bottom Line

This collection represents more than just everyday carry items – each piece has earned its place through quality, functionality, and personal significance. From the battle-tested Montblanc that accompanied me through my military career to the retirement gift ST Dupont that marks a new chapter, these items tell the story of a life well-lived.

The key to a great EDC isn’t about having the most gear or the most expensive items – it’s about choosing pieces that serve you well, bring you joy, and stand the test of time. Quality over quantity, always.

What are your essential everyday carry items? Share your thoughts and recommendations in the comments below.

Everything I Wore At Pitti Uomo 108: A Complete Style Guide 

Finally made it to Florence…

After an epic journey from DC to Rome, then by train to Florence, I’ve arrived at the stunning Bottega Veneta Suite at the St. Regis Florence. With the Arno River flowing right outside my window, this will be my base camp for the 108th edition of Pitti Uomo—and what a week it promises to be.

Understanding Pitti Uomo: More Than Just Menswear Theater

If you’re a casual menswear enthusiast who’s never experienced Pitti firsthand, the endless stream of photos might make it seem like nothing more than well-dressed men posing with cigars and Negronis—what I like to call the “influencer petting zoo” (trademark pending).

While there’s certainly some of that spectacle, Pitti Uomo is fundamentally the world’s most important menswear trade show. Held twice yearly at Florence’s historic Fortezza da Basso, it’s where global brands showcase collections to buyers and press, where industry trends are born, and where the business of menswear gets done.

Think of Pitti like a perfectly balanced Negroni—equal parts trade show, social events, and networking opportunities. Each component is essential to the whole experience.

My Four-Point Pitti Strategy

I don’t come to Florence just to stand around looking stylish (though that’s certainly part of it). My approach centers on four key objectives:

1. Networking: The menswear world is surprisingly intimate. Every conversation could lead nowhere—or everywhere. Building genuine connections remains crucial in this relationship-driven industry.

2. Brand Awareness: Beyond my online presence, the He Spoke Style Shop offers direct access to my entire tailored wardrobe through what I believe is the best value in online custom menswear.

3. Event Hosting: For three consecutive Pitti editions, He Spoke Style has partnered with Michael Andrews Bespoke and Angel Ramos New York to host memorable events, including our Monday night creative black tie aperitivo at the St. Regis Winter Garden—now known as Pitti’s unofficial opening ceremony.

4. Content Creation: Documenting the experience for our community while collaborating with partners creates lasting value beyond the week itself.

The Art of Pitti Dressing: Seven Themed Looks

Rather than pack randomly, our six-person team established daily themes to create visual cohesion while allowing individual expression. Here’s how I interpreted each concept:

01

Black Tie Creative

Sometimes the best creativity lies in restraint. You could argue that my interpretation isn’t overly creative, and you wouldn’t necessarily be wrong, but this represents exactly how creative I’m personally comfortable being within formal dress codes. My go-to strategy always revolves around selecting a standout dinner jacket that does the heavy lifting.

Man wearing light blue dinner jacket with pleated tuxedo shirt at Pitti Uomo 108 black tie creative event

This light blue option features incredible texture and breathable fabric perfect for Florence’s summer heat. The color makes a statement without veering into costume territory. I’ve paired it with a pleated front tuxedo shirt—my signature move for elevating formal looks beyond the standard.

White suspenders provide both function and classic appeal, while a coordinated stud set paired with vintage cufflinks adds personal history to the look. A midnight bow tie bridges the color palette beautifully, and patent leather loafers ground the ensemble with traditional formal footwear.

02

Tonal Tuesday

Earlier this year, I coined “Tonal Tuesday” and it resonated so well that it’s now become a recurring theme. While you might recognize elements from a previous video, I made key updates to keep it fresh and perfectly suited for Pitti. The foundation is an ivory twill suit that’s honestly become one of my favorite pieces of the season.

Ivory twill suit with sand chambray shirt - tonal Tuesday menswear outfit at Pitti Uomo

I’ve paired it with a sand-colored chambray shirt that creates subtle contrast through texture rather than color. This is where tonal dressing really shines—when you remove the distraction of contrasting colors, you focus on the interplay of textures and subtle shade variations. The chambray’s casual weave against the suit’s smooth twill creates visual interest without breaking the monochromatic harmony.

Brown suede accessories maintain this tonal approach while complementing the warm undertones, and vintage-inspired sunglasses add old-school sophistication. The overall effect is polished yet relaxed, perfectly capturing that effortless Italian elegance that Pitti embodies.

03

Technicolor

To be honest, I initially considered sitting out technicolor altogether. Lots of bold color isn’t my natural wheelhouse, but I found an approach that allowed me to participate authentically while staying true to my aesthetic. The key was discovering the perfect vehicle: a new merlot bamboo sport coat.

Merlot bamboo sport coat with pink shirt - technicolor theme outfit from Pitti Uomo 108

Bamboo fabric—sometimes called California cashmere—is magical for summer dressing. It offers cashmere softness while being significantly more breathable and practical for warm weather. The rich color provides the pop the theme demanded without feeling garish. I’ve supported the colorful jacket with a light pink shirt and ivory trousers that create a sophisticated tonal story.

The magic of bamboo extends beyond comfort—people literally cannot stop themselves from touching it, which creates wonderful conversation starters at an event like Pitti where networking is crucial.

04

Pitti PI

The “Pitti PI” theme presented classic Magnum archetypes: aloha shirt with nut-hugger jeans, or casual top with scandalously short shorts. This is Pitti, not Halloween, so I took that Tom Selleck inspiration and filtered it through my personal style lens. The centerpiece became a silk-cotton camp collar shirt that perfectly captures that relaxed Hawaiian vibe while maintaining sophistication.

Magnum PI inspired camp collar shirt and white trousers look from Pitti Uomo 108

The key styling decision was tucking it in—direct homage to Magnum’s always-tucked approach, but executed with tailored trousers rather than those infamous tight jeans. A ribbed t-shirt underneath adds comfort and authenticity to the tropical aesthetic, while white cotton trousers provide a clean foundation that’s decidedly not of the nut-hugger variety.

The baseball cap brings that essential sporty American element, while vintage-inspired sunglasses maintain the retro feel without becoming costume-like. What makes this work is finding balance between paying homage to an iconic character and creating something genuinely wearable for the setting.

05

Classic Black Tie

Wearing a tuxedo in summer isn’t a problem if you have the right tuxedo. This wool-mohair blend “truly tropical tuxedo” maintains all the elegance expected from black tie while being genuinely comfortable in warm weather. What I find fascinating about black tie is how deceptively simple it appears, yet countless small details must come together perfectly.

Tropical wool tuxedo with self-textured shirt - classic black tie look for summer formal events

I’ve chosen a self-textured tuxedo shirt to keep things ultra-classic while adding just enough visual interest to elevate beyond basic rental-wear territory. The coordinated stud set and cufflinks create consistency across metallic elements, while the silk cummerbund provides that essential finishing touch separating proper black tie from merely wearing a black suit.

The beauty of traditional black tie lies in its democracy—when executed properly, the clothes become a backdrop that allows personality and conversation to take center stage. There’s something liberating about knowing you’re dressed appropriately for virtually any formal occasion.

06

Bringing Preppy Back

Preppy style never truly goes away—it just takes periodic breaks before returning with renewed relevance. For this theme, I wanted to showcase a new sport coat that replaces a beloved piece that proved so popular it sold out completely. This alabaster glen plaid sport coat represents everything I love about preppy tailoring, with subtle plaid that provides visual interest without being overwhelming.

Alabaster glen plaid sport coat with blue OCBD - preppy menswear style at Pitti Uomo

The supporting garments read like a greatest hits of preppy essentials. The light blue Oxford cloth button-down is perhaps the most democratic piece of menswear ever created, while khaki cotton trousers create that effortless American ease that preppy style does better than any other aesthetic. The proportions are spot-on—structured enough to look polished but relaxed enough for long trade show days.

What elevates this beyond basic country club uniform is attention to details and proportions. The sport coat’s cut is contemporary while respecting traditional lines, and classic penny loafers with textured socks add visual interest at the foundation.

07

Black & White

A black suit in summer might seem questionable, but like the tropical tuxedo, this proves that fabric selection makes all the difference. Constructed in tropical wool, this suit maintains the visual impact of black suiting while remaining genuinely comfortable in Florence’s warmest weather. The real personality comes from the silk-cotton shirt with its fun pattern that’s perfect for summertime dressing.

Black tropical wool suit with patterned shirt - summer business attire with 1970s collar styling

The styling gets interesting with the collar worn outside the suit lapel, creating classic 1970s swagger that feels both nostalgic and contemporary. This detail requires attention to ensure the collar sits properly over the lapel both front and back, but when done correctly, it transforms the outfit’s entire attitude from corporate to creative.

Classic sunglasses add sophistication while ostrich leather shoes provide unexpected texture that elevates the look beyond standard business attire. The overall effect is polished but with personality—exactly right for Pitti’s unique blend of business and style theater.

The Complete Pitti Experience

These seven looks represent more than just outfit choices—they tell the story of how thoughtful dressing enhances every aspect of the Pitti experience. From networking opportunities created by conversation-starting fabrics to the confidence that comes from wearing perfectly fitted formal wear, each ensemble serves both practical and aesthetic purposes.

The beauty of Pitti lies in its unique combination of serious business and sartorial theater. Whether you’re navigating trade show floors, hosting evening events, or simply appreciating the incredible creativity on display, having a well-planned wardrobe allows you to fully engage with everything this remarkable week offers.

Most importantly, these outfits prove that developing your personal style doesn’t mean abandoning your comfort zone—it means understanding it well enough to stretch its boundaries thoughtfully. The best dressed men at Pitti aren’t wearing costumes; they’re wearing elevated versions of themselves.

Thanks, as always, for reading.

How to Style Black Penny Loafers: 5 Versatile Outfits 

We’ve all been there…

You’re browsing online, fall in love with something, buy it impulsively, and then when it arrives you’re left scratching your head wondering how to actually wear it. For me, this happens most often with footwear—and that’s exactly what happened when I received these gorgeous Myrqvist Stenhammar II penny loafers in black.

Black loafers seemed straightforward enough to style, but they didn’t click for me right away. After some experimentation and practice, I’ve put together five different outfits that showcase just how versatile these shoes can be. Here’s what I learned about styling black penny loafers.

The Key to Success: The Sandwich Method

Before diving into the looks, let me share the styling trick that made everything click. It’s called “the sandwich method”—a technique where your top and shoes are the same or similar color (the bread), with a contrasting color in between (the filling). This creates visual balance and was the key to making these black loafers work across multiple outfits.

01

Elevated Casual

Starting with an elevated casual look that’s perfect for spring and summer, I built this outfit around a simple yet sophisticated color palette. The foundation is a navy lightweight cotton twill chore coat layered over a heather gray t-shirt, creating that effortless layered look that works so well in transitional weather. The navy and gray combination is timeless and versatile, serving as the perfect backdrop for the rest of the outfit.

Man wearing black penny loafers with navy chore coat and white trousers in elevated casual outfit

For the bottom, I chose white cotton trousers and deliberately skipped the belt despite the belt loops. This keeps the look cleaner and more casual, preventing it from feeling too structured or formal. The white trousers brighten the entire ensemble and create a fresh, summery vibe that works beautifully with the darker tones up top.

The black penny loafers are the perfect finishing touch here, grounding the lighter elements while adding a touch of sophistication. Paired with no-show socks, they maintain the casual, breezy feel that’s essential for warm weather styling. The overall effect is polished but relaxed, making this outfit ideal for everything from weekend brunches to casual Friday at the office.

02

Old Money Modern

This outfit perfectly captures those coveted old money vibes while incorporating a modern high-contrast approach that feels fresh and contemporary. The foundation is a black cotton pique button-up shirt that provides structure and sophistication, serving as the anchor for the entire look. The texture of the pique fabric adds visual interest and prevents the black from looking too flat or monotonous.

Black penny loafers styled with cream sweater and stone trousers for old money modern look

The real star of this outfit is the cream cable knit cashmere sweater worn draped over the shoulders. I’ll be honest—this styling choice intimidated me at first, but it’s all about building confidence through practice and repetition. The cable knit pattern adds texture and visual depth, while the cream color creates a striking contrast against the black shirt. This combination of colors and textures is what gives the look its modern edge while maintaining those classic preppy undertones.

Stone cotton trousers complete the ensemble, bridging the gap between the high contrast of the top half. The addition of a black leather belt creates continuity with the shirt and shoes, while the stone color keeps the overall palette sophisticated and cohesive. The black penny loafers are essential here, echoing the black elements above and creating that sandwich effect that makes the whole outfit feel intentional and balanced.

03

Bringing Preppy Back

Drawing inspiration from classic preppy style, this outfit embodies that effortless, refined casual aesthetic that never goes out of fashion. The foundation is an ivory cotton canvas chore coat that brings both structure and casual coolness to the look. The ivory color is softer and more sophisticated than stark white, creating a refined base that works beautifully with the other elements.

Preppy outfit featuring black penny loafers with light wash jeans and ivory canvas chore coat

Underneath, an off-white t-shirt provides the perfect relaxed contrast to the more structured jacket. The slight tonal difference between the ivory and off-white adds subtle depth without being too obvious or contrived. This layering approach creates visual interest while maintaining the clean, preppy aesthetic that defines this style.

The classic light wash denim brings authentic Americana vibes to the outfit, and this is where the magic happens with the black penny loafers. Loafers with jeans is such a quintessential preppy move that instantly elevates casual denim from weekend wear to something you could easily wear to a nice lunch or casual evening out.

The navy baseball cap adds another classic preppy touch while providing practical sun protection, and the black loafers ground the entire look with their sophisticated presence. This combination proves that preppy style doesn’t have to be stuffy or overly formal—it can be relaxed, approachable, and thoroughly modern.

04

Tonal Summer Suit

This look demonstrates how to approach wearing a suit during warmer months while maintaining sophistication and comfort. The ivory twill suit is the perfect foundation for summer suit style—light enough to be comfortable in heat, yet substantial enough to maintain a polished appearance.

Summer outfit idea with black penny loafers and ivory twill suit

The key to making this tonal approach work is the sand-colored shirt, which provides just enough contrast to define the silhouette without being jarring. When working with colors this close in tone, texture becomes crucial. The sandy hue complements the ivory beautifully while adding warmth to the overall palette.

Here’s where the sandwich method really shines in formal wear. The black penny loafers provide the perfect anchor for this light, airy ensemble. They’re formal enough for suiting but relaxed enough for summer, and their dark presence prevents the outfit from feeling too ethereal or insubstantial. The contrast they create against the light suit is exactly what this look needs to feel grounded and intentional. A matching belt ties everything together, creating continuity between the upper and lower halves of the outfit.

05

Summer Business Casual

This final look represents the most conservative and versatile approach, perfect for professional environments where you want to look polished without being overly formal. The light gray hopsack sport coat serves as the ideal foundation—the hopsack weave adds texture and visual interest while the gray color remains neutral enough to work in virtually any business setting.

Professional business casual outfit with black penny loafers and gray sport coat

The crisp white button-up shirt is a timeless choice that creates clean contrast against the gray jacket. There’s something to be said for the power of a perfectly pressed white shirt—it instantly elevates any outfit and conveys attention to detail and professionalism. The key to achieving that perfect collar stand is using a collar support band, which might seem like a small detail but makes a significant difference in the overall polish of the look.

Classic charcoal trousers complete the ensemble, providing the perfect neutral base that allows the other elements to shine. Charcoal is one of those colors that works with everything, and these trousers bridge the gap between the lighter jacket and the dark shoes beautifully. In this more conservative look, I opted for visible socks, which is more appropriate for professional settings and creates a more traditional, polished appearance.

The black penny loafers are the perfect finishing touch for this business casual ensemble. They’re formal enough for the office but more relaxed than traditional dress shoes, striking exactly the right balance for modern business casual dress codes. This combination proves that you don’t need to sacrifice style for professionalism—the black loafers add a contemporary edge to an otherwise classic outfit.

About the Myrqvist Stenhammar II

These particular loafers are worth highlighting for their craftsmanship. The Stenhammar II is an apron-fronted penny loafer built on Myrqvist’s rounded, wider last number 21, finished with a thin half rubber sole. Designed in Stockholm and handcrafted in Portugal, they feature leather board heel caps, cork filling, and Goodyear welted construction.

Available in multiple options including box calf (which I chose), dark brown and black suede, dark brown calf, and black country calf, these shoes offer excellent quality at their price point.

The Bottom Line

Even experienced menswear guys, like me, sometimes struggle with new pieces. The key is to keep experimenting and practicing. I spent an entire morning putting together these five looks—it wasn’t magic, just persistence and creativity.

Whether you’re dealing with black penny loafers or any other challenging piece in your wardrobe, remember to try the sandwich method, don’t be afraid to experiment with different color combinations, and most importantly, keep practicing. Put in the work, and you’ll see the results.

What’s your go-to method for styling challenging pieces? Share your tips in the comments below.

Thanks, as always, for reading.

Tailoring Black Style: What To Know About The Met Gala 2025 Theme 

Today is the first Monday of May. For many this year that’s simply Cinco de Mayo, and for the fashion-obsessed like myself, it’s Met Gala Monday. 

Vogue does many things around this event, but clearly educating the public of what the event actually is is not one of them. While the event seems to be another moment for celebrities to peacock across a carpet, the night is actually a fundraising event for the Costume Institute. 

The fashion exhibit that is featured each year for the public (following the Met Gala) in the Metropolitan Museum of Art is created and curated by The Costume Institute, with this year’s exhibit called “Superfine: Tailoring Black Style.” This exhibit will “take the Black dandy as its subject, examining the importance of clothing and style to the formation of Black identities in the Atlantic diaspora.” 

The Met Gala itself is the evening of fundraising that has now become one of the biggest red carpets of the year, though in the beginning individuals simply wore something (fancy) from their closet, or a designer lent them an outfit that was already made versus the custom, one-of-a-kind expectations we’re now familiar with. What confuses most is that this event has its own dress code connected to the exhibit, this year’s being “Tailored For You.” 

While I am not personally educated enough to go into the history of the Black dandy, I am fascinated with (and slightly addicted to) the lead-up coming from Vogue this year – the covers, the editorials, the behind-the-scenes look from those involved…. that is what I want to unpack.

The Covers

To my knowledge, Vogue has never created a print issue with the exhibit’s theme prominently featured outside of one individual article, let alone the cover. For the May 2025 print issues, Vogue has not one but four covers featuring the event’s co-chairs – A$AP Rocky, Pharell Williams, Lewis Hamilton, and my personal favorite male fashion figure, Colman Domingo. 

I don’t know about you, but when I think of menswear and the men who genuinely care about style and have an impact on others’ style (whether you like that style or not), these four have absolutely changed the game.

The Meaning Behind the Editorials

These covers and the inside editorials were styled by Law Roach. Even if you don’t know who Law is, you’ve likely seen his work. He’s been the stylist behind Zendaya for roughly 13 years, as well as many other celebrities like Kerry Washington, Hunter Schafer, and Tom Holland. 

On the surface, these covers and editorials are absolutely beautiful on their own. But when you hear from Law himself, you understand that none of these images were done “just because.” Let’s take this editorial image of A$AP. 

While it may just look like a cool image on a NYC stoop, it’s actually a recreation, down to the stoop it seems, of a photograph of Langston Hughes. Or the editorial image of the tartan couple, inspired by the iconic red carpet duo of Sarah Jessica Parker and Alexander McQueen from the 2006 Met Gala. 

While menswear is absolutely having a more broadstream moment right now, these editorials do a wonderful job reflecting and honoring the long-standing history of Black culture’s impact in the menswear space.

I cannot pick a favorite, but I think the image that stood out the most for me because of the individuals in it was the one with Spike Lee, Lana Turner, Dapper Dan and Daryl Dismond. The impact these four have had – whether it’s Lee’s impeccable visual storytelling in his movies, Turner’s style showcasing what a Harlem socialite can embody, Dan’s re-embodiment of luxury fashion and hip hop, or it being “OK” for a man like Dismond to be the face of American fashion – goes far beyond one category, medium, culture or city. If any image speaks a thousand words, this image speaks one million. 

It’s worth also showing some of Roach’s other looks, including musicians Jon Batiste and Akeem Ali, athletes like Aja Wilson and Justin Jefferson, models Adut Akech and Tyson Beckford, and actors like Naomi Ackie, Aaron Pierre, Ayo Edebiri and LaKeith Stanfield.

One thing missing for me, though, is André Leon Talley. Yes, Anna talks about this dandy among the dandies” in her editor’s letter, and The Costume Institute will have some of his pieces in the exhibit. But I do think if there was any time to give this man his much deserved Vogue cover, this was it. 

I cannot predict what will happen on the red carpet, but I am confident that this year’s exhibit and red carpet will be history making. 

And while individuals like Jack Schlossberg are planning to “boycott” this year because of the seriousness of the world, I am one of many who believe that moments like this that fund the arts are more important than ever. Especially the year that is putting the history of black tailoring and its impact on a global stage. 

I will be watching every single moment of it with natural curiosity, ready to learn more stories behind the individuals that attend, the designers that create, and hungry for all of its beauty.