I was sitting in a diner on the Lower East Side last Thursday when this guy walks in wearing a top hat. Not like, an ironic beanie with a brim or something—a legitimate, Victorian-looking, Abraham Lincoln-style top hat. In April. In New York. Paired with what looked like a perfectly normal outfit otherwise: jeans, white tee, denim jacket. Just… and a top hat.
My breakfast companion—Marcus, my old college roommate who still insists bowling shirts are appropriate business casual—didn’t even blink. I, meanwhile, couldn’t stop staring. The guy carried himself with such unwavering confidence that for about thirty seconds, I actually questioned myself. Wait, are top hats back? Did I miss a memo? Is this guy so far ahead of the trend curve that I’m about to look like an idiot when every cool person in Brooklyn is wearing one next week?
Then Marcus caught me staring and just shrugged. “That’s his thing,” he said, like it explained everything. “He’s the top hat guy.”
And that, my friends, is exactly what I don’t want any of you to become.
Look, I get it. In a world where most men dress with all the creativity of an airport terminal at 6 AM, the desire to stand out is understandable. After years of writing about menswear, I’ve developed what you might call my own “signature elements”—I almost always wear a pocket square, I have a weakness for suede loafers in colors most guys wouldn’t touch, and I’ve been known to layer multiple necklaces in a way that makes my dad ask if I’m “trying to be a rapper now.” When you find things that work for you and make you feel good, it makes sense to incorporate them regularly.
But there’s a universe of difference between having a signature look and becoming a walking cartoon character. The pocket square guy. The bow tie guy. The guy who wears suspenders with literally everything including, I shit you not, swim trunks (saw this at a beach wedding in Miami, still having nightmares).
My buddy Eric—the one who got me my first style writing gig—went through a phase where he wore a scarf every day. Every. Single. Day. Summer included. Beach days included. Gym included. It started as a practical winter accessory, morphed into a security blanket, and eventually became his entire personality. When he finally showed up to a July rooftop party without one, three separate people asked if he was okay.
“I realized I had become The Scarf Guy,” he told me later, looking mildly traumatized. “People weren’t seeing me anymore. They were just seeing the scarf.”
That’s the problem with letting one specific item or style quirk define your entire look—it stops being an expression of your personality and starts replacing it. And worse, it locks you into a sartorial cage of your own making. The more people identify you with that one thing, the harder it becomes to ever appear without it.
So how do you develop a distinctive personal style without veering into cartoon territory? I’ve spent the last decade figuring this out through plenty of trial and error (and yes, I had my own scarf phase in 2014—there are photos, they will remain buried).
First, think in terms of subtle signatures rather than obvious gimmicks. The most elegant personal style often comes down to details that not everyone will immediately notice. Maybe you always cuff your jeans exactly the same way. Maybe you have a collection of vintage Timex watches you rotate through. Maybe you gravitate toward a specific color palette that works with your complexion. These are the kinds of personal touches that register subconsciously rather than screaming for attention.
My friend David, easily the best-dressed person in our friend group, always wears one small silver earring. Not a flashy stud, not something that demands attention—just this simple, almost utilitarian piece of silver in his left ear. He’s worn it so long that I forget about it until someone new meets him and mentions it later. “Oh, the guy with the earring?” And I have to think for a second before realizing, yeah, that is part of his look. But it’s not THE look.
The other key is flexibility. Your signature elements should be adaptable enough to work in multiple contexts. If your “thing” only works in one specific scenario, it’s not really your style—it’s a costume. I have a client who wanted to be known for wearing bold colored suits. Great in theory, but when he realized his bright purple suit wasn’t appropriate for his grandfather’s funeral or job interviews, he had to admit it wasn’t actually a sustainable signature.
Instead, he’s found that he loves bold colored socks. They work with suits for formal occasions (subtly visible when he sits), with casual outfits (rolled jeans), in professional settings (hidden when needed), and they satisfy his love of color without limiting where he can go or what he can do. That’s a signature that enhances his style rather than constraining it.
What’s worked best for me is thinking of signature style as a consistent approach rather than specific items. I tend to mix at least one traditional menswear element with something more casual or unexpected in most of my outfits. A tailored blazer with beat-up jeans. A crisp oxford shirt with vintage military pants. A formal overcoat with sneakers. This mixing of high/low, formal/casual has become my signature without forcing me to always wear any specific piece.
I once interviewed a 72-year-old style icon who’d been photographed for various menswear publications for decades. When I asked about his signature style, he looked genuinely confused. “I don’t have a ‘signature,'” he insisted, despite the fact that his distinctive way of dressing had influenced countless younger men. “I just know what I like and what works for my body and my life.”
That’s the sweet spot right there. The most authentic personal style doesn’t come from consciously trying to establish a trademark look. It emerges organically from a deep understanding of what works for you—physically, practically, emotionally—and the confidence to stick with it.
So how do you get there? Pay attention to patterns in your existing wardrobe. What do you reach for most often? What makes you feel most like yourself? What generates compliments that actually resonate with you? (Important distinction—if people compliment something but it doesn’t actually feel like “you,” that’s worth noting).
Experiment privately before committing publicly. Before you decide loud patterned shirts are your new signature, buy one or two and wear them in low-pressure situations. See how they actually feel on your body, in your life, with your existing wardrobe. The pieces that naturally integrate and that you find yourself reaching for without thinking—those are the foundations of your authentic style.
Consider your practical lifestyle needs, not just your aesthetic aspirations. My neighbor keeps buying beautiful suede desert boots that he sees in magazines, then leaving them in boxes because his commute involves six blocks of walking and our street floods every time it rains. Your signature elements should work with your life, not against it.
Remember that confidence is the ultimate signature, and nothing undermines confidence like feeling like you’re wearing a costume. If you’re constantly adjusting, explaining, or feeling self-conscious about an element of your outfit, it’s working against you, not for you.
The top hat guy from the diner? For all I know, maybe he’s completely comfortable. Maybe his great-grandfather was a Victorian undertaker and wearing that hat connects him to his family history. Maybe he just has an unusually shaped head that only a top hat properly fits. If he’s genuinely at ease and the hat is an authentic expression of himself, more power to him.
But I suspect that somewhere in his apartment is a collection of other statement pieces—the steampunk goggles, the massive pocket watch, the velvet cape—that he cycles through to maintain his position as The Guy With The Thing. And that’s the trap I want you to avoid.
Be memorable for having great style, not for wearing that one weird thing all the time. Develop the kind of signature that enhances how people see you rather than replacing you with a caricature. Find the sweet spot between bland conformity and costume-party peacocking.
And for god’s sake, leave the top hat at home unless you’re attending a presidential assassination. Just trust me on this one.
