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.”

Paul Sperry (1) came up with the Top-Sider after slipping on the topside of his sailboat (2) and falling into Long Island Sound. His design—inspired by his dog’s paw and borrowed from the grooves cut into rubber tires—created a durable, flexible shoe that gripped wet surfaces (3). Before long, the Top-Sider came in a range of stylish colors (4), though that grooved sole remains an unchanging selling point (5).
Courtesy of Sperry

“Boat shoe” was a generic term. What everyone was referencing was the Top-Sider, the shoe that’s been made for 84 years and counting by Sperry. As for the humble leather shoe (re)anointed by the arbiters of fashion, Sperry CMO Kate Minner has seen it all before.

“Every time you think it’s never coming back,” she said, “it comes back.”

Another way of looking at it, of course, is that it never really went away. Not unlike Converse’s high tops or the Weejun penny loafer, the Top-Sider has enjoyed a loyal coterie of fans that’s kept the shoe skipping along for generations now—even if the hipper versions that got the fashion press so excited are bit of a departure from the Authentic Original boat shoe. But we’ll get to that.

Courtesy of Sperry

Famous brands tend to have memorable founding stories, and Sperry is no exception, even if repeated telling has fogged a few of the details. It goes like this: One day in 1935, an avid sailor by the name of Paul Sperry was out on his boat, the Sirocco, when he slipped and fell into Long Island Sound. Traditional sailing shoes had soles made from either crepe rubber or coiled rope; neither worked well. Did that incident lead Sperry to create his famous shoe? Well, almost. The other story features Sperry back on dry land, watching as Prince, his cocker spaniel, navigated icy ground without slipping. In this version, Sperry took a closer look at the pads on Prince’s paws, where he observed a wavy, grooved pattern.

Fast-forward to Sperry’s workbench, where he cut a herringbone pattern into a slab of gum rubber, attached a simple canvas upper and put on his new shoes. On the wet decks of the Sirocco, Sperry kept his footing. A classic piece of footwear was born.

The Top-Sider name derives from “topside,” meaning the deck of a boat or ship. Initially, Sperry’s boat shoes were sold to the salty set: “The newest, smartest, safest thing in yachting gear,” stated an early ad. The U.S. Navy bought tons of Top-Siders during World War II. But by the 1960s—after Sperry had sold his interests to the Uniroyal rubber company—the shoes caught on with Ivy League undergrads. Sperry’s first headquarters in New Haven, Conn., were, after all, just blocks from the campus of Yale. And when 1980’s Official Preppy Handbook proclaimed the Top-Sider to be “authentic prep,” the shoe’s place in the closets of chino-wearing New Englanders—who happened to include Paul Newman and John F. Kennedy—was secured.

Sole Mates

Until about a decade ago, the Top-Sider’s notable selling point was that it was still your father’s boat shoe. But tradition only goes so far when it comes to luring younger customers. Starting in 2009, Sperry began partnering with fashion-forward brands—first Band of Outsiders, then Noah and Jack Spade and, most recently, Rowing Blazers. These labels (more than a little preppy themselves) applied their own touch to the classic Top-Sider silhouette, resulting in boat shoes made of tartans, tromp l’oeil prints and rugby-stripe foxing. At left is the Sperry X Rowing Blazers Seamate Croquet Stripe Boat Shoe designed by oarswoman Keziah Beall. It quickly sold out.
Courtesy of Sperry

None of which explains why Top-Siders were, in the past year, suddenly “back”—though Sperry’s numerous collaborations with famous designers (see sidebar) probably played a role. For her part, Minner believes that Sperry’s longevity has more to do with the shoe’s unusual combination of authenticity and adaptability. “It’s just a classic silhouette, people have fond memories of it and the brand has an innate ability to talk to multiple generations,” she said. “You can wear them as you want and style them as you want—and … you don’t have to be on or near a boat.”

Until about a decade ago, the Top-Sider’s notable selling point was that it was still your father’s boat shoe. But tradition only goes so far when it comes to luring younger customers. Starting in 2009, Sperry began partnering with fashion-forward brands—first Band of Outsiders, then Noah and Jack Spade and, most recently, Rowing Blazers. These labels (more than a little preppy themselves) applied their own touch to the classic Top-Sider silhouette, resulting in boat shoes made of tartans, trompe l’oeil prints and rugby-stripe foxing. At left is the Sperry X Rowing Blazers Seamate Croquet Stripe Boat Shoe designed by oarswoman Keziah Beall. It quickly sold out.

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

Recommended articles