The Story of the Boat Shoe

Clarkes tan boat shoes with khaki pants
Image is my own / All rights reserved

Boat shoes are among those rare items in the clothing world as likely to be worn by menswear nerds covered head to toe in madras and seersucker, as by the rugby jocks pantsing them.

While the boat shoe — also called a deck shoe or top-sider — has become a ubiquitous choice of footwear for people of all stripes, it’s origins are squarely maritime.

Boat shoes on a rock next to the ocean
Image credit: Jfernz ≠; Thatcher Clay / CC BY 2.0

In the early 1930s, New England yachtsman and former Abercrombie & Fitch employee, Paul Sperry was sprucing up the deck of his recently acquired schooner with a lick of paint, only to find when he set sail that, as he later put it, “a wet deck was […] a damn dangerous thing”. So dangerous, in fact, its slippery surface sent him careening overboard. 

Sperry set about in search of a solution. His first idea was to add emery powder to the deck, though this just turned the surface to sandpaper, which was less than ideal when met by exposed skin. 

So Sperry turned his eye to footwear instead, though here again it wasn’t all smooth sailing. The ropy espadrilles favoured by an English sailing company across the pond turned out to be unsatisfactory since they held up fine in the wet, but were weirdly slippery on dry surfaces. Rubber soles seemed like the next obvious port of call, but despite Sperry conducting hundreds of tests, these didn’t seem to work either.

Prospects of finding a slip-resistant solution looked grim. That is until a cocker spaniel named Prince entered the equation. While out with his dog, Sperry noticed that Prince coped just fine when running on slippery surfaces. Inspired by the rough grooves of his dog’s paw pads, Sperry cut a zigzagging pattern into a rubber sole and found it provided the perfect slip-resistant solution. Thus, the deck shoe was born.

In 1937 Sperry partnered with a Boston-based rubber company (called Converse, perhaps you’ve heard of it) to manufacture his new shoe, and two years later managed to patent his herringbone sole design.

At this point, the runway to market success awaited: Donald White, an advertising man and friend of Sperry’s, came up with the name Sperry Top-Sider and suggested their creator sell them at an aspirational $4.50 a pop by mail order, which at the time was still a newfangled sales technique. But orders rushed in, including ones by such notables as the Vanderbilts, who had a yacht crew to outfit, and the US Navy, who would enter the Second World War just two years later.

Vintage young man and woman dancing wearing boat shoes
Image credit: State Library of Queensland / No known copyright restrictions

A further boost in sales came a few decades later in 1980 with the publication of famed satire of all things Ivy and WASPy, The Official Preppy Handbook, by Lisa Birnbach. The book not only gives a shout-out to Sperry’s design as the OG of sailing shoes but puts a pair right on the cover, serving to cement the boat shoe as a preppy icon and footwear staple for years to come. 

A quick note on the style of the shoe. Apart from the unique tread already mentioned, top-siders have a number of noteworthy design features:

  • Rubber soles, originally in white to prevent them from causing any scuffing.
  • Typically leather uppers in dark shades to repel water and avoid stains (though these days you can get boat shoes in all manner of colour and material).
  • Handsewn, topstitched moccasin toes.
  • Rawhide laces looped through the back of the shoe and into (most typically) two eyelets at the front. The rawhide makes for easy knotting, especially when wet, while the 360-degree lacing system means you can cinch the collar of the shoe below the ankle as needed.
Sperry top sider boat shoes in tan with white sole
The Sperry Top-Sider
Image credit: Antontushnov / CC BY-SA 3.0

Sperry is still known for making the Top-Sider. You can see a nifty timeline with visuals on their site (including the sole Sperry originally carved with a penknife, as well as his patent design), and if, like me, you can happily watch people making shoes by hand for roughly the span of a natural human life, you can enjoy seeing the making of the Sperry boat shoe in this video (which is sadly a mere three minutes long). 

* In writing this piece, I’m especially indebted to Josh Sims’ entry on deck shoes in Icons of Men’s Style, which was where I first learned about Paul Sperry and the story of his shoes.

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