Today in 1939, New Haven-born sailor-turned-shoemaker Paul Sperry received a patent for one of the most famous and enduring pieces of American footwear: the Sperry Top-Sider, or “boat shoe.”

Born in 1895, Sperry’s life revolved around the sea; growing up along the Connecticut coast, he developed a lifelong love for sailing at an early age. He served in the U.S. Navy Reserve during World War I, and briefly went into business designing handcrafted duck decoys at ax’s end. In the 1930s, after slipping on the freshly refinished deck of his yacht and falling overboard into Long Island Sound, Sperry experimented with making a shoe that would better grip the smooth, lacquered, and often wet surface of boat decks.

Inspiration struck after Sperry observed his beloved cocker spaniel Prince run over a patch of ice without losing his footing. Intrigued, Sperry studied the bottom of Prince’s paw, and concluded the canine’s natural grip resulted from a series of intricate, fine grooves covering his footpad. Sperry converted Prince’s naturally-occurring paw patterns into a tight series of herringbone grooves, carved into natural white rubber, and placed the sole underneath a stylish, low-profile canvas shoe, and called his creation the Top-Sider — a reference to the shoe’s ability to grip the surface of slippery boat decks.

On November 14, 1939, Sperry received a U.S. Patent for his novel shoe sole design; by that time, he had already set up shop in New Haven and his Top-Siders were well on their way to becoming an American fashion icon. During World War II, he scored a lucrative contract with the U.S. Navy, providing thousands of slip-resistant boat shoes for American sailors and ensuring that his brand would be more popular than ever upon their return home. Further popularized by trend-setters like the Kennedy family, Top-Siders were firmly established as an East Coast fashion icon by mid-century, and are still regarded as a hallmark of “preppy” fashion around the world today.

Further Reading

Kat Eschner, “The Story of the Sperry Top-Sider,” Smithsonian Magazine

Sam Dangremond, “How Did the Top-Sider Get Its Name?” Town and Country

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