New York’s Best Street Style, Outside the Shows

Our style editor hit the pavement during this year’s New York Fashion Week and photographed his favorite street style looks

September 15, 2026 6:02 pm EDT
A man with a shaved head, sunglasses, and heavily tattooed arms wears a deconstructed brown vest over a gray t-shirt and patchwork shorts.
Nick Wooster, photographed on 65th Street and Madison Ave.
Christopher Fenimore

The Gist

New York Fashion Week SS27 brought out a fresh wave of street style, inspiring the author to document the diverse and often advanced menswear looks worn by industry pros and stylish New Yorkers. It proves that even the most unconventional outfits add to the city's unique fashion tapestry.

Key Takeaways

  • The article showcases street style photography from NYFW SS27, with a focus on menswear.
  • Featured individuals include fashion industry professionals, a professional athlete, and stylish strangers.
  • The outfits, while often advanced, are generally grounded in traditional menswear silhouettes.

I’ve always found inspiration in street style. Living in New York, all you have to do is take a walk and you’ll see interesting outfits, block after block, no camera needed. Still, everyone takes it up a notch during fashion week. I love seeing unique combinations I’d never put together. Obviously there’s some nonsense out there, too, but who cares? Even if it’s not to my taste, it’s eternally fun to see all the diversity NYC has to offer. I always have my camera on me, so last week, from showrooms to runway shows, I documented some of the stylish folks I met along the way. These are fairly advanced outfits from a grip of people who work in the fashion industry, but the vast majority pictured are grounded with traditional menswear silhouettes. That’s usually where my eye takes me. Hopefully you feel inspired to try something you see here.

All photos by Christopher Fenimore.

A man in a brown suede jacket, wide-leg jeans, and cowboy boots stands on a city sidewalk.
Christopher Fenimore

Akief Sheriff, brand image manager for Ralph Lauren, photographed on Sullivan Street. Yes, Akief works for Ralph, so his look is very Ralph. It can look costumey on some folks, but on Sheriff, it looks excellent.

A man with a beard and sunglasses wears a light blue and black striped cardigan, wide black pants, and black loafers on a city street.
Christopher Fenimore

New Orleans Pelicans forward Saddiq Bey, taken on Sullivan Street outside the Sebastien Ami NYFW pop-up event at & Son. It’s a clean fit. The proportions actually make him look shorter than he is, which might be the goal since he is a large dude.

A man with long hair and a "Desert Storm" cap wears a suit jacket, striped shirt, tie, yellow Muay Thai shorts, white socks, and loafers.
Christopher Fenimore

Preppy Pete of Gotham Galleria, taken outside the Sebastien Ami NYFW pop-up event at & Son. He’s a wild dude, and this is a wild outfit.

A man with dreadlocks, glasses, and a denim outfit stands on a city sidewalk, holding a phone.
Christopher Fenimore

Designer Sebastien Ami on Mott Street. With the right elements, the Canadian tuxedo is hard to beat, as evidenced by Sebastien here. Great choice of accessories, grounded by the simple deck shoes, which have been the menswear sneaker of the summer.

A man with blue hair and a white shirt with a graphic of a woman's face, black wide-leg pants, and neon green shoes.
Christopher Fenimore

Fashion stylist Daniel Jones Jr, taken outside the Sebastien Ami NYFW pop-up event at & Son. Daniel is teaching us a lesson in how to wear colors and how to ground them with something as simple as a black pair of pants and black socks.

Man in a gray blazer, light wash denim shorts, and black boots talks on a phone, wearing a yellow "Clement" cap.
Christopher Fenimore

I don’t know this dude at all, but I dig the cycling cap with the blazer. Also taken outside the Sebastien Ami NYFW pop-up event at & Son.

Man in a tan jacket, camo pants, and a flat cap, holding a bag, stands by a black car on a city street.
Christopher Fenimore

Photographer John Michael Arcella, taken outside the Sebastien Ami NYFW pop-up event at & Son. John Michael has been taking street style for many years, and his style is a bit of an amalgam of various menswear archetypes. When he puts it all together, it just works.

A man in a brown striped shirt, khaki pants, and a plaid cap stands on a city sidewalk, hands clasped.
Christopher Fenimore

Photographer and content creator Jeremy Mitchell, photographed on Sullivan Street. Jeremy told me his fit was not photography-worthy, but I told him I begged to differ. Jeremy has some of the cleanest style around. And I also really dig the way he handles brand partnerships. Everything about this guy feels very authentic.

Man in a red beanie, sunglasses, and "SHEPHERD" t-shirt stands in the middle of a city street.
Christopher Fenimore

Justin Boone, consultant, photographed on Sullivan Street. Justin is a badass, straight up. He’s always had killer style — the kind you can’t teach.

A man with short white hair, sunglasses, and tattooed arms wears a brown vest over a grey shirt and patchwork shorts.
Christopher Fenimore

Consultant and street-style god Nick Wooster, photographed on 65th Street and Madison Avenue. I’ve been photographing Nick for the entirety of my career. He’s an industry veteran with immaculate taste. Through fashion’s many trend cycles, Nick has always had a love of tailoring, and even with his more casual ‘fits, you can find tailored elements that help retain his elegance.

A woman with long dark hair wears a matching light brown short-sleeved button-up and wide-leg pants, with black sandals.
Christopher Fenimore

Mimi Fukuyoshi, SVP of Sales for Fear of God, photographed at Rockefeller Center. Those who know Mimi know she is a fashion industry titan. This outfit is low-key and relaxed and, again, highlights the kind of cool you can’t teach.

Christopher Fenimore

Samuel Hsin and Daniel Gu of Beijing design studio MotivMfg, photographed outside of Standard and Strange. I just met Samuel and Daniel before taking this photo, but I dig their respective styles, and I really dig the brand. Look out for something more in-depth from me on Motiv in the coming months.

A bald Black man in round glasses, an open black shirt, and wide-leg black pants stands on a city street.
Christopher Fenimore

Kyle Foxworth of Standard and Strange, photographed on Mulberry Street outside of Standard and Strange. Kyle is a cool dude. Super passionate about his job and the brands carried at Standard and Strange NYC. Don’t try this one at home!

Man in a brown cap, yellow shirt, and dark brown pants stands against a brick wall, hands in pockets.
Christopher Fenimore

Stylist Jon Alan, photographed on Prince Street in front of my favorite wall in the city. Just a simple outfit here that works well because A). Jon is handsome but B). He’s also trying not to do too much.

A man in a navy blazer, white polo, and jeans stands on a city sidewalk, holding a camera.
Christopher Fenimore

I don’t know Paul’s last name, but I know him from photographing with The Armoury, where he used to work. This one was taken outside of an event at Viberg, where he currently works, wearing a classic menswear outfit. Again, not trying to do too much, and the proportions and ‘fits of all of these pieces is ideal.

A man in blue sunglasses, an orange polo, navy blazer, khaki pants, and blue sneakers stands on a city sidewalk.
Christopher Fenimore

Nordstrom’s Men’s Fashion Director Jian DeLeon on the Mott Street side of my favorite wall. Jian has interesting personal style. His ‘fits don’t always land for me (nor should they), but I like his choice to mute the color of the polo with this soft A.PRESSE double-breasted blazer.

Two men in stylish, loose-fitting clothes smile at the camera on a city sidewalk.
Christopher Fenimore

Nick Andry of Alfargo’s Marketplace and No Man Walks Alone, and photographer Zane Gan, also of Alfargo’s Marketplace. Very different expressions of menswear here, but both look comfortable because they are.

Christopher Fenimore

Christopher Fenimore

Christopher Fenimore is a writer and photographer who splits his time between New York and Long Island’s North Fork. His work has appeared in GQ and Esquire, and you can find him here on Substack.
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