Sole Man: Paul Sperry's Top-sider

Jun 25, 2014

Eighty years ago an inventor and sailor created an attractive shoe with a nonskid sole that could perform in all conditions. He called it the Top-Sider, and it’s among the best-selling designs in American menswear to this day. As is often the case, he found its inspiration in nature.

Paul Sperry was the scion of an old New England family with one side of its history tied strongly to the sea. His great-grandfather, Captain Sereno Armstrong, had been a master mariner in the South Pacific, and thrilled a young Paul with tales of high adventure among marauders and cannibals. On the other side of Paul’s family, men were farmers and businessmen. Sperry was a product of this divide, working at the Pond Lily Company of New Haven, a textile plant founded by his father, and sailing on weekends. In the 193os, he bought a schooner from a Nova Scotia shipbuilder and had her sailed to his hometown in Connecticut.

The standard “boat shoes” of the time were crepe-soled sneakers, like Sperry had worn in the Navy during WWI. They were suitable for dry decks, but lousy on wet ones. When the painted deck of his boat was awash in rain or rough seas, Sperry discovered his kicks could even be deadly. Using the skills he’d learned at Pond Lily, he set about devising a sole that would “stick like a barnacle” in any weather.

“I began to think about a nonskid sole and literally made hundreds of experiments,” Sperry told a 1977 audience at the New York Yacht Club. “One morning, when the snow was covered by ice, I let my cocker spaniel out to exercise.” Sperry expected his dog to slip, but it didn’t, so he turned the spaniel over and examined its paws: they were covered in tiny cracks and grooves running in all directions.

Inspired, Sperry headed back to his workshop. He took out his penknife and carved up a gum-rubber sole, experimenting with a number of different tread patterns until he landed on the herringbone crosshatch that would make him famous. He glued the soles to an ordinary pair of sneakers and gave them to a deckhand to test. The next time Sperry saw him, the deckhand was carrying a bucket of water. “Watch!” the boy said, spilling his pail onto the deck.

“He took a running start on the wet deck, and I expected him to break his neck or fall overboard, but instead he stopped dead in his tracks,” Perry recalled. Sperry wrote to all 5oo of his fellow Cruising Club of America members, the most experienced yachtsmen in the country, describing his nonskid soles and asking for their feedback. In return, he received 497 requests for pairs of his newly christened Top-Siders, which kickstarted a mail-order business. In the 194os, he received his first big sales boost when the U.S. War Department named Sperry’s Top-Sider an official shoe of the Navy. Two decades later, President Kennedy was photographed vacationing seaside wearing a pair on his yacht. Today, Top-Siders are synonymous with New England nautical taste and classic preppy panache like few shoes before or since.

They continue to be defined by their purpose—to keep your rear end separate from the deck in all conditions, without leaving a mark. That’s an assist in looking good.

The rest is up to you.

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