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The Shoe That Conquered Dry Land: A Brief History of the Boat Shoe

How a sole inspired by a dog’s paw went from racing decks to frat houses to the runway—and why it’s seaworthy again.

In the winter of 1935, a Connecticut sailor named Paul Sperry watched his cocker spaniel cross a sheet of ice without slipping and decided the dog knew something he didn't. Sperry had spent years falling down on the wet deck of his schooner, once clear into the Long Island Sound, and no sole on the market gripped a thing once the spray came over the rail. So he flipped the dog over, studied the cracked pads of its paws, and went at a piece of rubber with a knife until he'd carved the same fine network of cuts into it. The grooves channeled water and bit in every direction. He had invented siping, the boat shoe, and a century-old debate about who gets to wear it.

Every part of the shoe that now looks like style began as a fix. The hand-sewn moccasin upper flexed with a working foot. The rawhide lacing pulled it snug when the boat heeled over. Leather, tanned to take salt water, held its shape through a soaking, and the white siped sole, the dog's contribution, bit into wet wood without scuffing it. None of it was a matter of taste. Sperry sold the first pairs by mail to the Cruising Club of America, and by 1939, the U.S. Navy had made the Top-Sider regulation issue, strapping it to the feet of sailors who'd never seen the inside of a yacht club. For its first quarter-century, the boat shoe was exactly what it advertised: a tool for not dying on a wet deck.

Then it came ashore, and the troublemaking started. By the 1960s, the shoe had drifted off the working docks and onto the lawns of Newport, Rhode Island, the house slipper of a moneyed New England at play. Prep schools took it up, then the colleges those schools fed, and in 1980, Lisa Birnbach's Official........

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