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

The shoe has stayed popular beyond the preppy crowd

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.”

Click for more from this issue

This story first appeared in the Oct. 7, 2019, issue of Adweek magazine. Click here to subscribe.