The Sperry Top-Sider Was Inspired by Rubber Tires and a Dog’s Paw

The shoe has stayed popular beyond the preppy crowd

The classic boat shoe didn't leave marks on the deck.
The classic boat shoe didn't leave marks on the deck. Courtesy of Sperry

A rare bit of agreement echoed through the fickle world of fashion in the past year. It began when GQ announced that “Boat shoes are back.” Next came Esquire: “Yep, boat shoes are cool again.” Newcomers such as the website Valet piped in: “The classic preppy shoe has returned.”

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This story first appeared in the Oct. 7, 2019, issue of Adweek magazine. Click here to subscribe.
@UpperEastRob robert.klara@adweek.com Robert Klara is a senior editor, brands at Adweek, where he specializes in covering the evolution and impact of brands.
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