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

Winter 2023 Men's Streetwear Looks: 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].

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 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



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