They started out in the mid-‘30s as a niche product for civilian seafaring types, and later, sailors in the US Navy. But that all that changed when Ivy Leaguers took to them in the subsequent decades with such fervor that by the 1980s they merited an entry in the original WASP-identification field guide, The Official Preppy Handbook. More recently, boat shoes have found their way into almost every stylish guy’s closet, and it’s easy to see why, since their understated, utilitarian character couldn’t be more versatile.
Credit for those functional good looks, not to mention boat shoes’ invention, goes to Paul Sperry, or better yet, his dog Prince. The avid boater was in need of better traction on his schooner’s top deck and noticed the cocker spaniel’s ability to grip an icy surface during a stroll one winter day in 1935 Connecticut. After examining his Prince’s paws and their wavy patterns, Sperry cut a series of wave-like grooves (known as siping) into the soles of his shoes with a penknife, thus creating the first iteration of the now-standard boat sole. When it came time to produce a proper version of the new Top-Sider, he finished it off with a moccasin toe and details that took visual or functional cues from the shipyard, from open lacing and exposed seams to non-marking rubber soles. Four years later, in 1939, the Navy secured Sperry’s design for their sailors, amping up production and allowing Sperry to expand in civilian and enlisted markets alike.
By 1946, Sebago was on the scene, though it wasn’t until the late ‘60s that they introduced Docksides. The two companies are still the main players on the scene to this day, but collaborations with the likes of Band of Outsiders, the Paris-based Colette, and J.Crew show just how far the boat shoe has come on the style front.
Now, whether manning the decks or strolling the city sidewalks, a classic (or not-so-classic) pair of boat shoes is a great match for pretty much any casual occasion. Go simple—and give a nod to the old school preps—with slim chinos and a polo. Or dress down a tailored look by pairing them with a lightweight khaki suit. Either way, just be sure to skip the socks. Wearing boat shoes any way other way than barefoot is reason enough for, if not a good keelhauling, at least stern sartorial talking-to.