Straight Up Streetwear for Winter 2022
Colin Clark

Best Men’s Streetwear Looks of Winter 2023 Go All-in on Casual Cool

“The best fashion show is definitely on the street. Always has been, and always will.” photographer Bill Cunningham once said. And Cunningham would know, as he spent nearly 40 years capturing street fashion for The New York Times. This winter, if you’re looking for the best men’s streetwear looks with eye-catching style, check out some of our favorite pieces.

Winter 2023 Men’s Streetwear Looks: All-in on Casual Cool

Get the look (above): Nanamica Coach Jacket & Chino Pants [$690 & $260; us.nanamica.com]; Hugo x Replay Capsule Logo Print Sweatshirt [$160; hugoboss.com].

Man wearing Paul Smith Blue/White Checked Double Breasted Overcoat, Paul Smith Fit Two Button Suit, and Paul Smith Floral Shirt

The Key to Looking Put-Together for Fall/Winter 2022? Deconstructed Looks

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Man wearing a sweater and riding a skateboard through a tunnel.
Colin Clark

Dsquared2 Plaid shirt [Price upon request; dsquared2.com]; J. Lindeberg Alpaca Sweater [$215; jlindebergusa.com]; Chimala 8oz. Painter Pant [$585; shop.180thestore.com]; Common Projects White Sneakers [$445; commonprojects.com].

Man standing with a skateboard and wearing two shirts.
Colin Clark

Louis Vuitton Graphic T-shirt & White Shirt [$1,090 & $1,040; louisvuitton.com]; Death To Tennis Barber Pants [$350; deathtotennis.com].

Man wearing a blue flannel shirt walking next to a red outdoor fireplace with mountains in the background. flannel shirts

The Best Men's Flannel Shirts for Fall 2022

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Man wearing a sweatshirt and sitting on a bench.
Colin Clark

Knickerbocker Big Cat Sweatshirt [$135; knickerbocker.nyc]; AKNVAS Werner Plaid Pants [$550; aknvas.com]; DSquared2 Cotton & Silk Shirt [Price upon request; dsquared2.com]; Common Projects White Sneakers [$445; commonprojects.com].

Man wearing a sweater vest and skateboarding.
Colin Clark

Dsquared2 Cotton & Silk Shirt [Price upon request; dsquared2.com]; Knickerbocker Cable V-Neck Sweater & Cord Teddy Pant [$195 & $250; knickerbocker.nyc]; Common Projects White Sneakers [$445; commonprojects.com].

Man walking through the woods wearing camouflage jacket and orange midlayer

Fall 2022 Style Preview: Fashionable Outerwear for Men

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Man wearing a velvet jacket and pants.
Colin Clark

DSquared2 Velvet Jacket and Pants [Price upon request; dquared2.com]; The Cast What The Hell Tee [$35; thecast.com].

Man wearing a cardigan and holding a skateboard, standing in a doorway.
Colin Clark

Knickerbocker Alpaca Brushstroke Cardigan [$345; knickerbocker.nyc]; Sunray Haleiwa S/S T-Shirt [$90; shop.180thestore.com]; Gramicci Pleated Trousers [$130; gramicci.com]; Common Projects White Sneakers [$445; commonprojects.com].

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