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Today, Sperry Top-Siders come in a variety of styles and colors.

It was a brush with death paired with a dog’s surefootedness that inspired the now-classic piece of footwear: the boat shoe.

In the 1930s, Paul Sperry was an executive at New Haven’s Pond Lily Co., a dyer and finisher of fabrics and shoes. In his spare time he would often take to his beloved sailboat, a cutter named Sirocco, on the waters around Connecticut’s coast. Sailing was part of Sperry’s family: His great-grandfather had regaled him as a boy with tales of the South Seas, and Sperry’s younger brother, Armstrong Sperry, would become a celebrated writer of sailing adventures, winning the Newbery Medal for his 1940 work Call It Courage.

But Paul Sperry’s own sailing adventures didn’t always go smoothly. According to the Sperry company’s official history, after sailing through unusually rough seas, Sperry slipped on the wet deck and fell overboard, almost dying in the process. After this harrowing experience, he decided to try to make the sea a safer place by designing a shoe with better traction. The existing shoes for boating were merely ordinary leather shoes with rubber soles. Sperry wanted a shoe capable of gripping boat decks even when they became slick with water, as they inevitably would.

He began working on various designs, but with little success until the winter of 1935, when he watched his dog run without slipping across the ice on a cold Connecticut day. He examined his four-legged friend’s paw and noticed the pads contained an intricate pattern of cracks. These natural grooves helped account for the animal’s surefootedness. Sperry decided to imitate those patterns. “He experimented with cutting patterns of grooves into gum-rubber shoe soles,” The New York Times noted in 1986. “Through trial and many errors, he finally discovered that slits carved into a sole in parallel herringbone patterns afforded the superior grip he was after.”

In 1939, 80 years ago this month, Sperry was granted a patent for what would become the world’s first boat shoe. The most popular early design was the Sperry Top-Sider. It quickly became an in-demand item for boating enthusiasts. Many members of the Cruising Club of America wrote Sperry to request a pair of the shoes, and at the outbreak of World War II, Sperry attracted what is arguably the best client for a boating-related product: the U.S. Navy, which named the Top-Sider one of its official shoes.

U.S. Rubber bought the Top-Sider patents shortly after they were granted, but Sperry continued with the company as a consultant. And the boat shoes continued to increase in popularity. They had already conquered the high seas, but they were destined for success on land as well. Not only were the shoes comfortable, they came with an implied sense of status few other products did. After all, if you had boat shoes, the implication was that you had a boat. Landlubbers began to clamor for them. In the 1960s the Kennedy family was photographed wearing the shoes, and they became popular on college campuses and among surfers.

In 1980, The Official Preppy Handbook endorsed the shoes, cementing their link to popped-collar fashion. These days the shoes enjoy continued popularity and are worn by men and women alike during the summer months.

Earlier this year, Nick Sullivan, Esquire’s former fashion director, was asked by a reader of that magazine if it was OK to wear socks with boat shoes. “Listen carefully and no one need get hurt,” he wrote in response. “Never put boat shoes and socks in the same sentence again — the best-dressed sailors always go bare ankle.” 

This article appeared in the November 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email editor@connecticutmag.com, or contact us on Facebook @connecticutmagazine or Twitter @connecticutmag.

The senior writer at Connecticut Magazine, Erik is the co-author of Penguin Random House’s “The Good Vices” and author of “Buzzed” and “Gillette Castle.” He is also an adjunct professor at WCSU’s MFA Program and Quinnipiac University