Sperry Shoes: Not the Average Shaggy Dog Story

Sperry Cloud CVO shoes viewed from behind
Image is my own / All rights reserved

As anyone who has ever left their slippers unattended around a puppy can attest, it’s rare for a story involving a dog and a pair of shoes to have any sort of happy ending. Not so, however, in the case of Paul Sperry and his cocker spaniel named Prince.

The year was 1935. Paul Sperry, a New England native with salt water in his veins, had just a few years earlier bought himself a boat. Known as the Sirocco, Sperry’s schooner represented a lifelong passion for the outdoors and the open water in particular. He had been born in 1895 in the coastal city of New Haven, Connecticut, his grandfather worked as a shipbuilder before the American Civil War, and a young Paul had himself spent a year in the Naval reserve back in 1917. Sperry took to sailing like a fish to water and fully immersed himself in all things seafaring. Which is why, when he tumbled overboard one day after skidding about atop the Sirocco, his immediate response was to contrive some solution to the problem of slippery boat decks.

Sperry’s first solution proved somewhat less than propitious. Rather than beginning with shoes, his initial plan was to paint a boat deck with a layer of emery dust. His application proved successful…at least as far as grip was concerned. ‘But,’ as Sperry himself explained, ‘if any part of the human anatomy came into touch with them, it was like giving yourself a rub down with sandpaper.’

So Sperry set his sights on shoes instead. At the time, there wasn’t much available by way of sailing footwear. One popular option was an espadrille-type design with coiled rope soles that held up well enough in the wet but was unworkably slippery on a dry deck. So Sperry looked to rubber as a more viable alternative. Once the sailing season came to an end, he spent the winter of 1935 trying to devise a slip-proof rubber sole.

Paul Sperry Razor Siping patent-1937
Paul Sperry’s shoe sole patent
Image credit: United States Patent Office / Public domain

He conducted hundreds of experiments to this end but nothing worked. It wasn’t until one lucky winter day when Sperry took his cocker spaniel out for a walk that a solution finally presented itself. Seeing Prince dash across the ice, Sperry was struck by the realisation that his dog had little trouble keeping his balance on the icy terrain. He first thought it was thanks to Prince’s claws, but upon closer investigation realised it was really down to the hundreds of tiny lines and cracks running along the underside of his trusty companion’s paw. It gave Sperry an idea that would change his life — and the world of footwear — forever.

Sperry quickly set about trying to replicate the texture of Prince’s paws by cutting grooves into a rubber outsole. It was the first step to creating his patented ‘Razor Siping’ sole and the very first Sperry Top-Sider. That shoe would come to be known as the Circular Vamp Oxford, or CVO for short (Somewhat confusingly, the term ‘Top-Sider’ has been used by Sperry to describe both this early cotton iteration and the later leather version of their boat shoes, while common usage tends to ascribe it only to the latter). The CVO consisted of an upper made of quick-drying cotton that was attached to a rubber sole using a heat-sealing method known as vulcanisation. The results were groundbreaking and effective, not to mention stylish and comfortable, which no doubt accounts for the continued popularity of the CVO among Sperry’s offerings today.

Sperry’s first deck shoe retailed at an impressive $4.50 (for context, the most expensive tennis shoes at the time went for just $3.75) and Sperry sold them via mail order, which was a groundbreaking sales method at the time. He apparently did so at the urging of Donald White, an advertising man from McGraw Hill, although he is also said to have consulted with famed mail order poineer Leon Leonwood Bean. Just like L.L. Bean did when he was starting out, Sperry decided to go straight to his target demo by writing to every member of his yacht club. He was duly inundated with orders and demand for his shoes snowballed from there. Sperry’s shoes were worn by everyone from the Vanderbilt yacht crew to the shoppers at Abercrombie & Fitch, who were an important early retail client for the fledgling brand. The real windfall, however, came when Sperry landed a contract to supply shoes to the US Navy beginning in 1940 — just one year prior to America entering WWII.

Sperry leather Top-Sider boat shoes
Leather Top-Topsider boat shoes, Sperry’s most popular shoe model
Image credit: Antontushnov / CC BY-SA 3.0

Naturally, Sperry’s success didn’t stop with the invention of the CVO. Within just two years, in 1937, the company’s most iconic offering arrived in the form of the leather Top-Sider (also known as the Authentic Original or AO), a boat shoe that combined Sperry’s trademarked non-slip, siped soles with a sturdier upper made of animal hide that had been specially tanned for coping with repeated exposure to salt water. It also featured moc-toe stitching and a cinching lace system that wrapped around the back of the shoe to tighten the collar at the ankle for added stability. 

To this day, the leather Top-Sider remains Sperry’s best-selling model and set the ball rolling on the their enduring success. By the 1960s, the brand had become firmly associated with the glamorous, seaside lives of America’s elite. Sperry’s appearances throughout popular culture only added to the allure. The Kennedys wore them, as did Paul Newman, Mr Rogers, and Bob Denver’s titular hero on Gilligan’s Island. The hype only grew when both Richard Dreyfuss and Robert Shaw donned navy CVOs in Jaws in 1975 and when Lisa Birnbach’s famous 1980 satire The Official Preppy Handbook put a pair of Top-Siders right on its cover.

While the CVO and the leather Top-Sider loom particularly large among Sperry’s offerings, the brand has steadily added new shoes to its catalogue since the end of the Second World War. From the narrow world of boating they have expanded to encompass other sports, industrial footwear, and shoes built for everyday leisure. They also expanded into sports sponsorships, beginning with the America’s Cup and the U.S. Olympic sailing team in 1987, and, in addition to their perennial footwear and seasonal output, they have long engaged in prolific brand collaborations, the first of which was with New Balance as far back as 1994. 

Man wearing Sperry boat shoes
An example of a newer style from Sperry’s shoe catalogue
Image is my own / All rights reserved

The brand’s founder, Paul Sperry, passed away in 1982 at the ripe old age of 87. Although he had long since handed over the reins of the business, he did live long enough to witness his creations become icons, sufficiently so to seemingly consolidate an entire way of life (It’s not for nothing that Lisa Birnbach advised every self-respecting prep to get a pair of boat shoes, regardless of whether they actually owned a boat). It seems safe to assume Paul would have been pleased. What’s less clear is what Price made of it all, although what with all of his inspirational ice-bound scampering, he probably had far more important things to worry about.


*The Sperry shoes worn above were gifted courtesy of Rich London PR.