The nautical-meets-collegiate shoe was created in 1935 (yep, 90 years ago!) by Paul Sperry after he slipped off his boat but noticed his dog, whose paws were naturally non-slip, didn’t. Inspired, Sperry cut patterned grooves into blank rubber shoe soles, developing the world’s first non-slip boat shoe, according to the brand. Typically defined by grippy rubber soles, sturdy leather laces, water-repellant and stain-proof materials (apart from the trendy suede styles), and a sleek silhouette reminiscent of a loafer-moccasin-driver hybrid, boat shoes are functional but also surprisingly… fashionable?
A few years later, they became the official shoe of the U.S. Navy. Then when President John F. Kennedy casually sported them in the 1960s, they cemented their place as a preppy wardrobe staple. In 1980, The Official Preppy Handbook, written by Lisa Birnbach, even featured Sperry Top-Siders on the cover, calling them a preppy essential. Since then, brands like G.H. Bass, Sebago, and Tod’s have also become synonymous with the style.
