Last month I was standing in line for coffee when I noticed the guy ahead of me—complete stranger, mid-thirties probably, nothing remarkable about his overall appearance. Navy sweater, gray pants, brown shoes. Standard-issue business casual. But then I spotted it—his sweater cuffs were slightly pulled up, revealing not just any shirt underneath, but one with a subtle contrast of blue chambray fabric at the cuff edges. That single detail told me this random dude in a Chicago coffee shop wasn’t just wearing clothes—he was getting dressed with intention. It’s what my buddy Trevor calls “the menswear handshake”—those tiny signals that fly under the radar of 99% of people but speak volumes to the initiated.
I’ve spent years documenting these subtle markers of style fluency. Not the obvious flex points like visible logos or statement pieces, but the quiet details that separate the guys who really understand clothing from those who are just following a checklist. These aren’t about spending more money or chasing trends. They’re about the kind of attention to detail that demonstrates genuine engagement with how clothes are made, worn, and combined.
The thing about these signals is that they’re practically invisible unless you know what to look for. My dad still can’t understand why I care about whether my jeans are selvedge or why I’ll spend fifteen minutes discussing collar roll with a shirtmaker. “They’re just clothes,” he says, completely missing that for some of us, they’re a language—one with dialects, slang, and inside jokes that only make sense if you’re part of the conversation.
Let me walk you through some of these subtle signals that make me instantly recognize a fellow clothing enthusiast—not to create some exclusive club, but because understanding these details might help you make more intentional choices about how you present yourself.
First, there’s what I call “the architecture of ease”—the way clothes fit in a manner that’s neither too tight nor too loose, but precisely relaxed in the right places. It’s the sport coat that hugs the shoulders but allows room through the chest. The trousers with a clean line but enough room to sit comfortably. This deliberate balance communicates more style knowledge than any designer label ever could. Watch a genuinely well-dressed man move in his clothes, and you’ll notice he never looks restricted or suffocated. That natural harmony between body and garment only comes from understanding how clothes should function, not just how they should look in a mirror selfie.
I remember interviewing a 70-year-old Italian factory owner who showed up wearing what appeared to be a very simple outfit—navy blazer, gray trousers, light blue shirt. But watching him reach for his espresso, I noticed how his jacket sleeve revealed exactly the right amount of shirt cuff (about half an inch), how the collar of his shirt sat perfectly against his neck with just the right amount of space, how his trousers broke exactly once over his shoes. Nothing was pulling or straining. The entire effect was one of completely natural elegance that probably took decades to perfect but looked totally effortless.
Then there’s the subtle art of fabric knowledge. I can spot a guy who understands quality materials from across a room. Not because he’s wearing something obviously expensive, but because he’s chosen fabrics appropriate to the season, the setting, and the garment itself. Cotton oxford cloth for casual button-ups. Tropical wool for summer suits. Hefty denim for jeans that will actually develop character over time. The guy wearing lightweight worsted wool trousers in January is missing something fundamental, no matter how expensive they were.
My friend David, who runs a fabric mill in Scotland, can identify different wool qualities by touch alone. I once watched him rub a suit sleeve between his fingers at a dinner party and correctly identify not just the approximate weight of the fabric but the likely country of origin. That’s an extreme example, but developing even a basic understanding of appropriate fabrics is a game-changer for personal style. It’s why that stranger’s chambray cuff caught my eye—he understood that subtle textural contrast adds complexity to an otherwise simple outfit.
Color coordination is another arena where the subtle signals shine. Not matching—matching is actually kind of a rookie move. I’m talking about the sophisticated understanding of color relationships that allows someone to pair a deep burgundy knit tie with olive chinos and a light blue shirt in a way that feels intentional rather than random. Or knowing that camel, navy, and cream create a timeless palette that never looks forced.
The worst style advice ever given was probably “make sure your belt matches your shoes.” It creates this bizarre paint-by-numbers approach to getting dressed. The more nuanced truth is that colors should complement rather than match, should consider skin tone and setting, and should demonstrate that you understand the difference between coordination and uniformity. I once complimented a total stranger on his combination of a forest green jacket, burgundy scarf, and mid-blue jeans. “Thanks,” he said. “My wife laid it out for me.” Honesty I appreciate, and hey, recognizing when someone else has better color sense than you is its own form of style wisdom.
Then there’s the matter of appropriate formality—understanding not just dress codes but the unwritten rules of different contexts. I can immediately spot the guy who grasps that certain environments call for soft tailoring rather than structured suits, who knows when a knit tie communicates more style awareness than silk, who understands that loafers without socks work for summer cocktails but not winter weddings. This isn’t about rigid adherence to rules but about demonstrating social awareness through clothing choices.
Last year at a media event in New York, I watched a sea of identical navy suits and white shirts part around one guy in a tobacco linen jacket, cream trousers, and suede loafers. He wasn’t more formally dressed than anyone else—arguably less so—but he understood the environment well enough to know that relaxed elegance would stand out more than corporate uniformity. That contextual awareness is impossible to fake.
The patina of well-worn quality is another subtle signal that never fails to catch my eye. I’m not talking about artificially distressed anything—that’s the opposite of what I mean. I’m referring to the natural aging of quality pieces: the leather briefcase that’s darkened at the handles from years of use, the waxed cotton jacket with creases that tell the story of its owner’s movements, the shell cordovan shoes that have developed a rich glow from careful wearing and maintenance.
My most prized possession is a Filson bag that’s traveled with me to twenty-seven countries over twelve years. The canvas has faded unevenly, the leather straps have darkened to a rich honey color, and the brass hardware has developed a gentle patina. I once had a guy follow me for half a block in an airport just to ask about it. Not because it’s flashy—it’s objectively not—but because it has the indefinable quality that only comes from the genuine intersection of quality and time. You can’t buy that off the rack.
Some of the most telling details live at the level of what menswear nerds call “handwork”—the visible evidence of artisanal construction techniques. The slight puckering around the edges of a hand-rolled pocket square. The barely perceptible pick stitching along a jacket lapel. The hand-sewn buttonholes that aren’t quite as mechanically perfect as machine-made ones. These small imperfections actually signal higher quality, not lower, communicating to those who know that this garment wasn’t mass-produced.
I remember touching the lapel of a stranger’s jacket at a wedding (after asking permission, I’m not a complete weirdo) because I could tell from across the room it had the telltale roll of canvas construction rather than fused. “Bespoke?” I asked. He nodded. “London?” Another nod. We spent the next twenty minutes comparing notes on our favorite tailors while our respective partners rolled their eyes. That lapel was like a secret password into a conversation most people didn’t even know was happening.
Proper shoe care might be the ultimate subtle flex. Nothing tells me more about someone’s style sensibility than the condition of their footwear. Not the brand or the style, but how well they’re maintained. Shoes that have been properly polished, conditioned, and cared for—even relatively inexpensive ones—will always look better than neglected expensive pairs. The guy wearing Grant Stone loafers that have been impeccably maintained will always look more stylish to me than someone in scuffed Ferragamos.
My dad taught me how to polish shoes when I was twelve, setting up newspaper on the kitchen floor and showing me how to work the wax into the leather with small circular motions. “Always take care of your shoes,” he said, “and they’ll take care of you.” It’s still some of the best style advice I’ve ever received. When I see someone wearing well-maintained footwear, I know they understand this fundamental truth.
There’s also the question of proportion—the relationships between collar sizes and face shapes, jacket lengths and body types, tie widths and lapel widths. These aren’t arbitrary rules but visual harmonies that, when properly observed, create a sense of balance that registers subconsciously. The guy who understands that his broader face looks better with a slightly wider collar spread, or that his height is better complemented by a longer jacket, is demonstrating a nuanced understanding of how clothes work with his particular body.
I once watched a salesman at a high-end department store try to sell a client on a suit with incredibly narrow lapels. The client was a former football player with shoulders approximately the width of a doorframe. The proportional mismatch was painful to witness. Finally, another salesman stepped in and redirected him toward a more classically proportioned option that actually complemented his build. The client couldn’t articulate why the second suit looked better—he just knew it did. That’s the magic of proper proportion.
The balance of trendy versus timeless is another subtle signal. The most stylish guys I know incorporate just enough contemporary elements to look current without becoming fashion victims. Maybe it’s a slightly more relaxed trouser silhouette this season, or a textured knit rather than a traditional silk tie. These small concessions to current trends, incorporated thoughtfully into an otherwise classic wardrobe, demonstrate an awareness of fashion’s evolution without surrendering to its more extreme whims.
My colleague Marcus is a master of this balancing act. His wardrobe is fundamentally traditional—navy blazers, gray flannels, oxford shirts—but there’s always one element that places him firmly in the present moment. Last week it was the slightly chunkier derby shoes that nodded to current footwear trends without going full Frankenstein monster. Before that, it was the subtly oversized fit of his otherwise classic camel topcoat. He’s never the most fashion-forward person in the room, but he’s never the most dated either.
Perhaps the most elusive signal of all is genuine comfort in one’s clothes—not just physical comfort, but psychological ease. You can always spot the guy who’s wearing a suit because he wants to versus the one who’s been forced into it for an obligation. The former moves differently, carries himself with a natural confidence that comes from knowing his clothes are an authentic expression rather than a costume.
I frequently speak at college campuses about men’s style, and I can always identify the students who are experimenting with dressing up because they’re genuinely interested rather than because they think it’s what they’re “supposed” to do for job interviews. There’s a subtle but unmistakable difference between the guy awkwardly tugging at his tie knot all day and the one who’s forgotten he’s even wearing one because it’s become a natural extension of his self-expression.
So why do these subtle signals matter? It’s not about creating some exclusive club where only certain people “get it.” It’s about understanding that real style operates at a level deeper than trend-chasing or label-hunting. It’s about developing a relationship with clothing that transcends consumption and enters the realm of genuine cultural literacy.
When I notice that stranger’s perfectly aged leather watch strap, or the guy who’s had his off-the-rack blazer tailored to fit just right, or the subtle texture mixing of a wool tie against an oxford shirt, I’m recognizing a shared appreciation for quality, intention, and detail. It’s less about judgment and more about connection—the quiet acknowledgment between people who speak the same visual language.
The irony is that to most people, these signals are completely invisible. My girlfriend still laughs at how excited I get about finding undarted shirt construction or hand-sewn buttonholes. “Nobody else notices these things,” she tells me. And she’s mostly right. But that’s exactly what makes them powerful as style markers—they’re not for everyone else. They’re for you, and occasionally for those few others who speak the same dialect of this strange language of men’s clothing.
So keep noticing those chambray cuffs peeking out from under sweaters. Keep appreciating the perfectly broken-in leather boots. Keep recognizing the subtle interplay of textures and proportions that elevate simple clothes to personal expression. Not because they signal membership in some exclusive club, but because they demonstrate the kind of attention to detail that makes getting dressed an act of intention rather than mere necessity.
And maybe next time you’re in line for coffee, you’ll catch someone studying your cuff as it reaches for your wallet, noticing that you, too, get it.
