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How do you wear Sperry boat shoes? With or without socks?

Elizabeth Drori, Sperry Chief Marketing Officer, strikes a happy medium. “The Sperry Authentic Original boat shoe is a timeless classic. Socks or no socks, with cuffed jeans or a skirt, wear them in a way that expresses your personal style.”

When sailor and inventor Paul Sperry created the first non-slip boat shoe in 1935, he inadvertently launched one of the most enduring debates about personal style in the history of fashion: Do you wear boat shoes with or without socks?

Very few style statements evoke such a polarized response.  John Legend, Sperry’s Global Brand Ambassador, threw down the style gauntlet recently, stepping out in his cropped trousers and boat shoes asserting his bare ankles.  “It depends on the cut and fit of your pants, and how cool you are,” he says of his sockless style.

Retailer J. Crew’s men’s style team shows Sperry boat shoes worn with their playfully patterned socks, while author of the New York Times bestseller Men and Style, David Coggins, prefers the sockless look.  “We can’t have our feet shackled with grotesque tube socks, corseted and constrained,” he says. “Go forth with a liberated ankle!” 

For those who want to wear socks with boat shoes, Brian Davis, owner of Wooden Sleepers, a New York based vintage American menswear brand, online store, and showroom sets some guidelines. “First things first – no ‘fun socks.’ This is not a time for stripes, argyles, or novelties. Grab a crisp pair of white cotton socks and wear with your favorite chino shorts (cut above the knee!) and pair with a worn-in polo, rumpled oxford cloth shirt, or breezy patch madras.  For a cooler day, substitute the shorts with a pair of chinos (not too slim, not too baggy) or a lighter wash denim like a broken in 501, and a vintage military shirt, cotton sweater, or chore coat,” he instructs.

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Others, like menswear editor and owner of the sock brand Bombas, Randy Goldberg, find a happy compromise in the no-show sock, cut low especially to be worn with boat shoes, without being seen. “Once the no-show sock is inside your Sperrys, it will disappear completely, giving you the advantage of stealth comfort. Sockless looks, sock feels. Best of both worlds,” he says.

Elizabeth Drori, Sperry Chief Marketing Officer, strikes a happy medium. “The Sperry Authentic Original boat shoe is a timeless classic. Socks or no socks, with cuffed jeans or a skirt, wear them in a way that expresses your personal style.”

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