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FWYNN FASHION BLOG

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. 

The Unassuming Power Suit 

A gray suit is a power suit that wields its influence with subtlety.

“I had noticed men were much more confident in their clothes. So I sought through trouser suits, trench coats, tuxedos, and pea coats to give women the same confidence.” — Yves Saint Laurent

Without using the term “power suit,” Saint Laurent identified the essence of the power suit as a garment that both creates and exudes confidence in and from the wearer. And while the term likely brings to mind a traditional combination of a navy suit, crisp white shirt and bright red tie, there’s much more to the power suit than any single color combination, fabric or cut.

Today I want to share how the underrated gray suit deserves a prominent place in the power suit conversation. Let’s dive in.

What Is a Power Suit?

For better or worse, one’s appearance typically delivers the first impression. Because of this, the power suit is the go-to uniform for many of life’s biggest professional moments. When one wants to both feel and express confidence, capability and control, there’s nothing better than a power suit.

As with everything, the proper power suit starts with the perfect fit. Suits traditionally emanate a sense of strength through their cut, but an ill-fitting suit undermines this message. In other words, it doesn’t matter how well you may have nailed the power suit “formula” if your clothing doesn’t fit well.

The power suit is not defined by a particular color, but it must not venture beyond traditional, conservative colors. The power suit is not intended to convey individuality, creativity or fun and this sense of familiarity and tradition helps frame and compliment, rather than distract from, the wearer. 

Solid, not overly intricate patterns are typically worn with the suit, shirt, tie and socks, but simple, traditional patterns such as the pinstripe suit or striped tie are power suit staples. 

How Can A Gray Suit Be A Power Suit?

Bright red is the established power tie color because of what we associate with the color either consciously or unconsciously. It grabs attention, like red lipstick. Matadors in red are incredibly masculine. In nature, the color often communicates danger. Humans use it for stop signs and red lights. 

If navy blue is the color of professional power, gray is the color of power under control.

So what do we associate with the color gray? The answer tells us why the gray power suit makes so much sense. Instead of the kind of power that is attention-seeking, bold and aggressive, gray reminds us of different facets of power. Here are three:

  1. We first think of gray being associated with more advanced age, wisdom and trust. It’s neutral, which can help establish an air of fairness and objectivity that may be extremely powerful in certain settings.
  2. Grays are often associated with sleekness or modernity, like the Guggenheim Museum in Bilbao.
  3. Finally, gray has an industrial, concrete sense that conveys gravity and longevity.

It’s easy to think of professional moments where one might want to convey wisdom, professionalism, sleekness or gravitas. These are different sides of the power coin to the red discussed above and, in a more nuanced sense, the traditional navy blue power suit.

The navy blue power suit is great and I won’t try to talk you about of it as navy blue brings elements of tradition (military uniforms) and trust (as the expected choice). Two powerful elements to project. If navy blue is the color of professional power, gray is the color of power under control.

The HSS Medium Gray Twill Suit

What’s my go-to gray power suit? Our very own medium gray twill suit, of course. Featuring a rich twilled wool from the venerable Vitale Barberis Canonico who has been creating quality fabrics in Italy for more than 350 years, it’s a versatile staple of my wardrobe.

You can customize the styling many different ways to suit — sorry, not sorry, for the pun — your own tastes, but I personally prefer the classic two button, double vented jacket with a notch lapel and flap pockets. The double venting adds a bit more modernity than the single vent, very much in line with out motto of “classic style, modern sensibility,” while the notch lapel maintains the more conservative focus.

For trousers, I like side adjusters with a single reverse pleat and two-inch cuff, but again these can all be made to your preferences and specifications when ordering from the HSS Shop.

How I Styled It

One of the great things about gray is how easily it pairs with so many colors. A light gray suit looks great with a light pink or pastel green shirt, but those combinations are for different occasions. 

For the power suit styling, I paired my medium gray twill suit with a classic white shirt, black tie with white stripes and simple white pocket square for that all-important sliver of contrast. It’s a look that’s pulled together without being loud or commanding attention. This classic combination belongs in any decade as it would have looked just as good in the Mad Men era of Madison Avenue as it does today in Midtown. I feel confident wearing it and it really suits my style as it projects confidence in a refined and subtle way.

Of course you will want any accessories to complement the outfit rather than stand out and make their own statements. My classic Datejust along with a pair of wholecut Oxfords fit the bill perfectly.

The Bottom Line

We need not think of gray suits as forgettable, drab, or boring. Instead, when worn with confidence as part of a well-considered wardrobe in the right setting, it can convey subtle, nuanced power in a way you may not have thought possible.

The gray power suit need not replace the navy blue power suit. I do, however, hope that you will consider adding it to the rotation for the right occasions. After all, it’s these slightest nuances and attention to detail that make men’s style so fun and interesting.

Thanks, as always, for reading.

An Unforgettable Evening In Florence With St. Regis & The Dalmore 

The unofficial “opening ceremony” for Pitti Uomo 107.

I think it’s safe to say that our pre-Pitti Monday night creative black tie kickoff event is legitimately now a “thing.”

Following our inaugural effort last summer for Pitti’s 106th edition and the incredible feedback we received from our attendees, we decided it was high time to up the ante a bit by combining forces with our partners from Michael Andrews Bespoke and Angel Ramos NY as well as our great friends at St. Regis Florence, The Dalmore, and Davidoff Cigars.

The result: another spectacular and unforgettable evening.

The St. Regis Florence stands as one of Italy’s most prestigious luxury hotels, housed in a historic palace designed by Brunelleschi in the heart of Florence. Originally built in 1432, the building was converted into a grand hotel in the mid-1800s, and today represents the pinnacle of Florentine elegance and sophistication.

The hotel’s prime location along the Arno River offers breathtaking views of the historic city, while its meticulously restored interiors feature hand-painted frescoes, crystal chandeliers, and custom furnishings that pay homage to Florence’s rich artistic heritage. Each area of the property is uniquely decorated, combining Renaissance-inspired décor with modern luxury amenities, making it one of the most distinguished addresses in Florence.

The evening unfolded below the dramatic arches framing the St. Regis’s prestigious Winter Garden Bar, where guests were welcomed with two signature cocktails created by the St. Regis’s intrepid bar staff as well as four incredible expressions from The Dalmore — King Alexander III, Cigar Malt Reserve, Port Wood Reserve, and everyone’s favorite 18 year old.

Midway through the evening, after guests had arrived and had time to mingle and reconnect with each other, each partner from the MAARNY group — Cory Sylvester, COO of Michael Andrews Bespoke; Brian Sacawa, founder of He Spoke Style; and Angel Ramos, creative director of Angle Ramos NY — and Dan Loeser, single malt specialist from The Dalmore took the opportunity to welcome attendees and thank our hosts and sponsors.

Following the remarks, guests were treated to the signature ceremony of the St. Regis — the art of sabrage — and one more signature cocktail, featuring The Dalmore topped with champagne.

Jamie Ferguson

Patrick Osborne Fox

Gui Bo

Kevis Manzi

Robert Spangle

Brian Sacawa & Enuri Acosta

Tomasso Capozzoli

Nicolo Radano

Tony Bader

Alessandro Squarzi

Elijah Kumar

Guilia Guidi

Bunny Cordeaux

Michèle Free

Buzz Tang & Brian Sacawa

Ian Meiers

Max Poglia

Mickael Korausch

Jonathan Edwards & Luke Alland

Virna Gambini

Douglas Cordeaux