How We Dress Now

The rule book is officially out the window. Men’s fashion is more fluid now than ever. Sure, that means getting dressed is a little more fraught—but it’s also exponentially more exciting. To provide inspiration, we went looking for men who dress confidently across the spectrum of personal style. The folks on the following pages aren’t professional fit gods and Instagram kings. They’re regular guys living regular lives who happen to have tastes that are strong, unique, and worthy of your consideration—and emulation. They’re authentic to themselves. And that’s what matters. So here’s to the bold and the brave—and the guys who can put together one hell of a look.

bailey anderes content, creator and barista, 21

Suit by Aleksander Manamis; shirt by Black Comme des Garçons; shoes by Paul Harnden shoemakers; glasses by Rigards; artisanal Ukrainian neck scarf from If Soho; ring by Eskhaton, Møsaïs Paris, and Clocks and Colours; earrings by Maya Noach.


Bailey Anderes

Content Creator and Barista, 21

“I was the kid that would wear suits to high school. My style is old-fashioned, artisanal, eccentric—like the Victorian period. In an age of fast fashion, mass markets, and easy, quick trends that dissipate from the public eye within a week, the antithesis of that is the fashion that I’m interested in and the fashion that’s really good. It’s the slow, archaic production that doesn’t correlate with trends.”

keshida layone, visual artist and director of business development, 47

Tunic by Arielle & Melissa; trousers and earring by H&M; hat by Wilde & Lovely; cuff from street fair in Brooklyn; stone ring from Junior League thrift shop in Philadelphia; sterling-silver ring by Aea Jewelry.


Keshida Layone

Visual Artist and Director of Business Development, 47

“I feel like I was born into fashion. In middle school, I was using staples for hemming, just to try to get the look, even though during the day it’d be unfolding and unraveling. Now, as a visual artist, I’m attracted to almost anything. I love the African-diaspora style, along with streetwear. Then you move into classic, simple, elegant menswear brands—I like to play around with everything and not take things too seriously.”

george inaki root, ceo and creative director of milamore jewelry, 35

Shirt and trousers by Kapital; watch by Audemars Piguet; belt by Noah; jewelry and necklace (used as wallet chain) by Milamore.


George Inaki Root

CEO and Creative Director of Milamore Jewelry, 35

“I don’t really have one fashion icon, but I like to walk around the city and get inspired by people I see on the street—all those random, different styles. I like to be edgy, mixing in jewelry. Blazers make me feel confident. They can be cool—they don’t have to be formal; you can pair them with shorts and a leather boot.”

preview for How We Dress Now

sean crowley, owner of crowley vintage, 42

Jacket by Anderson & Sheppard; shirt and scarf by Drake’s; trousers by Hertling; tie by Ralph Lauren; shoes by Church’s; watch by Hamilton; pocket square by Polo Ralph Lauren; vintage tie clip; socks by J. Press.


Sean Crowley

Owner of Crowley Vintage, 42

“My grandfather was the beginning of fashion for me. I used to hang out at his house watching old British period pieces, and I was completely overwhelmed and charmed by the style, especially the tailoring, from the turn of the century to the ’50s. He was a women’s designer and a great dresser. It was just in the air, having beautiful fabric and detail and color around. I’ve had a bunch of great teachers along the way, but he was the start.”

s mckinley frantz, architect, 25

Coat by Suitsupply; sweater by Sid Mashburn; trousers by Knickerbocker; shoes by Nike; hat by Naadam; glasses by Spier & Mackay; bag from Etsy seller; scarf, Frantz’s mother’s own.


S. McKinley Frantz

Architect, 25

“When I was six or seven years old, my aunt was working for Ralph Lauren. I begged her to bring me into the city to design my own sweater. It would have looked ridiculous, but as early as that, I had a healthy interest in fashion. Now I work in architecture and interior decorating. Putting together an outfit is very similar to decorating. It’s about finding the balance of high and low, formal and informal, and how big the gap between the two is going to be that day.”

armand manoukian production associate, 24

Jacket by Bode; Lakers T-shirt from NBA Store; customized jeans by Levi’s; watch by Seiko; belt by Burberry; glasses by Warby Parker.


Armand Manoukian

Production Associate, 24

“I like prep and colors, but I try to make everything I wear look worn and washed. It shouldn’t be too contrasty; you have to balance things. I also like to go for a look and then tone it down with one thing. You go for prep, and then you put on a baseball cap or slightly cooler sneakers to throw it off just a little bit. You don’t want to look too into it.”


Jacket, bag, and sunglasses by Brandon Blackwood; trousers by Koven; shoes by Maison Margiela; belt by Asos; ring by Tiny Lux.


Desmond Sam

Publicist and Event Producer, 28

“I’m Guyanese and Trinidadian, so my Caribbean heritage is definitely a big take on my inspiration. I’d describe my aesthetic as a bit bipolar, fun, eclectic, and honestly, a bit immersive. I find my aesthetic to be as if I can be my own chameleon, diving within different aspects of myself. My friends always say, ‘We can go to the gala, or we can go to the trap house.’ We’ve got looks for both!”

Photographs by Ryan Slack


Trishna Rikhy is the Associate Style Commerce Editor at Esquire. Previously, her writing has appeared in Vogue Runway, PAPER Magazine, V Magazine, V MAN, and more. She is based in NYC, but can probably be found wherever the strongest cup of coffee is.

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