“How We Dress Now” is something of an experiment. At nine editions of Esquire around the globe, we set out this fall to discover if, far from the realm of the fashion runway and the celebrity stylist, real men, living in diverse places, have what it takes to reflect and develop their personal style in the clothes they wear. The answer, we found, is a resounding yes! Here, we celebrate men of all ages and backgrounds, men who use their own clothes to project a unique sense of self, injecting personality and authenticity into every stitch. One thing is clear: personal style takes time and passion, but it’s worth it.
Below are the twelve men selected for Esquire from the New York area. Then scroll down to links to the galleries from the other eight international editions of Esquire. The combined results from all nine editions unveil Tuesday at Pitti Immagine Uomo, the storied Florentine trade show that has been at the center of modern male style for over half a century.
“I’ve always been into collegiate chic—vintage athletic threads—and I often pair those with elegant workwear. I’m all about a well-fitted silhouette.”
The Takeaway: Simple workwear exudes great style. But only if you get the fit just right.
“My dad was a suit-and-tie man, a huge influence. He always looked clean and handsome. I grew up in Cleveland in the ’70s and ’80s. There was a sense of occasion back then. We dressed up to go to dinner or even get on an airplane.”
The Takeaway: All suits are not the same. Find a reliable tailor or a brand that fits your body shape perfectly. And stick to it like glue.
“The foundation of my sense of style comes from my father, who took pride in setting himself apart from the pack with his fashion. I remember seeing him walk my neighborhood in his clothes as if he was on a runway.”
The Takeaway: Experimentation is key to building your personal style. Try things that shouldn’t work together. You never know.
“I describe my style as business casual evolved. My day-to-day requires that I look put together, but I want to present myself in a way that doesn’t look cut from a catalog. Clothes are sort of my business card.”
The Takeaway: The old suit-for-work rules went out the window a while ago. But that doesn’t mean you are exempt from setting certain standards for yourself. Identify them and stick to them.
“My clothes help to create the vibe I need that day. This look is imitating some high-end casual look and rock- musician style. I like the balance of elegant and wild.”
The Takeaway: Mixing a vintage leather jacket with simple basics creates interesting tensions.
“I always wanted those hand-sewn, semi-cordovan high-tops from Feit. But I have realized that wanting an object is sometimes more fulfilling than actually having the object. There is some magic in that distance. I like the tension.”
The Takeaway: Style is an ongoing adventure in self-expression. And color is the fastest way to communicate your youness.
This article appeared in the Winter 2021 issue of Esquire
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“My Ralph Lauren alpaca trench coat is what I would grab from my closet if my apartment were on fire. I saw it at Harrods during a Thanksgiving trip a couple years ago. It’s my favorite thing to wear out and about in New York, because I inevitably get heckled while wearing it.”
The Takeaway: If you live somewhere cold, a topcoat is the piece the most people will see you in. It shouldn’t be an afterthought.
“I feel confident when I’m wearing clothes that feel natural on me—when things aren’t contrived. Even when I’m in tailoring, I try not to take it too seriously. If you find yourself fidgeting with or thinking about an outfit throughout the day, it’s become a costume.”
The Takeaway: Putting your clothes together should always look effortless. But getting there requires effort.
“I’m a little bit country with some East Coast grit. I grew up watching The Dukes of Hazzard and Clint Eastwood movies. I was around a lot of race cars, motorcycles, big rigs, and hot rods. A lot of good style influences to pick and choose from.”
The Takeaway: Clothes are context—a clear manifestation of the interests and passions that fill your life.
“My red 40 Acres and a Mule letterman jacket holds a special place in my heart. When I was twenty, my first internship was at Ecko Clothing. They didn’t pay me, but they gifted me this amazing jacket from Spike Lee’s clothing line for my hard work. I’ve had the jacket for eighteen years. It reminds me to keep the same energy that got me here. Always work smart and be open to opportunities.”
The Takeaway: Clothes with stories behind them are always more interesting and lasting than something you just bought on a whim.
“I always found it interesting that people dress from their shoes up. I decide on pants and build from that. I tend to find a pair and wear it straight for weeks, and then find inspiration from another combination and build around that for the next few weeks.”
The Takeaway: Don’t ever expect to achieve the perfect wardrobe. Good style is about being open to possibilities for change.
“I find my clothes all over the place. I like to maintain balance, and I love mixing high and low. For example, if I buy a $300 pair of pants, I love wearing them with a shirt I got for five dollars off eBay or at the thrift store. Some items I need to act fast on buying or I’ll miss out, but most of the time I’m digging through eBay for hours on end to find the perfect piece.”
The Takeaway: High/low mixing is a great way to give your clothes personality without breaking the bank.
