Every era has its share of pioneers and mavericks, but there are only a select few who manage to personally define an entire lifestyle through their work. Paul Sperry is one such individual. He invented the non-slip sole that was the foundation for the boat shoe. The company he founded in his own name, Sperry Top-Sider, expanded the horizons of sailing, perfecting the art of preppy fashion at the same time. Over the last 80 years, Sperry has grown from the simplest of ideas to one of the world’s most understated footwear brands. Time to take a step back as we look at the origins of this quirky company.
Paul Sperry was born in 1895 in New Haven, Connecticut, a coastal city steeped in ocean-going tradition. From his formative years, Paul had an affinity for the outdoors and there was never any doubt that salt water ran deep in his veins. He resented spending too much time in the classroom, preferring to hunt, ski and sail around New Haven.
After Paul’s schooling years were complete, his father, Sereno, purchased the Pond Lily Company, which specialised in processing textiles. Meanwhile, Paul heard the call of the wild and headed off to join the Naval Reserve in 1917. After a year of service, Seaman First Class Sperry was released from duty with a headful of nautical know-how and steely military discipline – solid foundations for his impending career. Paul duly began work at the family firm as a salesman, while simultaneously starting Sperry Natural Decoys, which manufactured duck hunting accessories. This was the first time Paul was able to combine his passion for the outdoors with his natural aptitude for business.
In 1925, he married a New Haven-born girl named Pauline. They would spend the rest of their lives together, but their first adventure was a honeymoon to Chesapeake Bay, duck hunting in the bone-chilling cold. That might not be everyone’s idea of a romantic getaway, but Paul Sperry was a devout outdoorsman.
As the 1930s arrived, Paul resolved to buy a boat. His grandfather had been a ship builder before he served in the American Civil War, and Paul inherited his keen eye for ocean-going vessels. He purchased a schooner named Sirocco and as the years passed, he and Pauline became increasingly enthralled by the marine lifestyle. They immersed themselves in the salty life, joining the Offshore Sounding Club and the New York Yacht Club, spending as much time as they could sailing from coast to coast.
Late one night on Long Island Sound, Paul Sperry slipped and fell from the deck of the Sirocco. Everyone was fast asleep, but he was fortunate enough to grab hold of some rigging and somehow clambered back on board. Years later, when he was asked what motivated him to create the non-slip boat shoe, he responded succinctly, ‘Because I fell overboard, that’s why!’
At that time, boating footwear consisted of either canvas uppers with a slab of crepe rubber glued to the bottom or shoes with coiled ‘rope’ soles. Crepe was the preferable material, but it was slippery when the deck was wet, whereas the rope sole would slip when it was bone dry. Sailing barefoot was not an option, as those foolhardy enough to try it regularly broke their toes.
Once the sailing season came to its conclusion, Paul Sperry was a man on a mission. Through the winter of 1935, he spent hour after hour in a makeshift workshop at his New Haven home, experimenting with rubber combinations as he searched for an elegant solution to slippery soles. One freezing cold day, he pulled himself away from his work to clear his head, stepping out into the snow with his Cocker Spaniel, Prince. Paul watched the dog run across the frozen landscape with ease and he began to wonder how Prince was able to stay upright so easily. His first thought was that the dog’s claws must be digging into the snow like a track-runner’s spikes, but as Prince turned and ran towards him, he realised this wasn’t the case. Inspecting the dog carefully, the curious inventor observed something that would change his life forever. Paul Sperry had an idea.
Racing back to his workshop, Paul took out a chunk of gum rubber a quarter of an inch thick. Using a razor sharp blade, he proceeded to make parallel cuts in the rubber material a fraction of an inch apart, almost all the way through. When that was pressed against a wet piece of polished metal – with the pressure applied at right angles to the cuts – the traction was dramatically increased. So far, so good. But when he applied pressure in the same direction as the cuts, the rubber became slippery. Paul quickly realised that cutting the rubber in a zig-zag herringbone pattern – known today as ‘siping’ – was the perfect solution he had been looking for. He glued some hand-cut rubber to the base of an old pair of shoes and the first Sperry Top-Sider prototype was complete.
The Top-Sider Sets Sail
After experimenting on board the Sirocco, Paul confirmed first hand that his siping design did indeed prevent slippage. He led for a patent and it was time to take his exciting new product to the market. To his surprise, the United States Rubber Company refused to produce the revolutionary soles stating that their complexity meant it would retail for $4.50, at a time when the most expensive tennis shoe was only $3.75. Many might have given up at this point, but Paul Sperry was an adventurous spirit and not easily deterred. He struck a deal with a rubber company in Boston to produce blank soles to which he would apply the siping himself, using a machine of his own unique design.
The first model in production was the Canvas Circular Vamp Oxford, or CVO for short. The upper had a simple design with a single piece that swept back to the side of the foot, with a quarter panel on either side. The shoe was lined with cotton so it could dry quickly, while the rubber sole was attached with a new heat-sealing method known as vulcanisation. The shoe was surprisingly stable and downright comfortable too.
The first Sperry Top-Sider was initially sold through direct mail channels. Paul sent letters to every member of his yacht club and was immediately inundated with orders. The word was out and Paul received a huge order from his old friend Frank Howard at Abercrombie & Fitch. Paul told Howard that he couldn’t afford to sell his shoes wholesale, but a few days later he received another huge order. The pair negotiated a wholesale price that kept the retail tag manageable and the deal was done. It didn’t take long before the Sperry Top-Sider had made its way to every corner of the USA.
Paul Sperry was a natural innovator. The success of the Canvas CVO was encouraging, but Paul knew he could produce a sturdier leather version of his non-slip shoe – he just hadn’t quite figured out how. Between 1935 and 1937, Paul Sperry developed the design that is now synonymous with the term ‘boat shoe’. The leather Top-Sider, known as the Authentic Original, or AO, was the first to utilise the classic moccasin toe stitching as well as the iconic ‘saddle’ lacing, where the shoelaces wrap around the ankle to tighten up the collar.
Paul also came up with a new way of tanning leather so that repeated exposure to salt and water wouldn’t crumble the shoes to bits. The Authentic Original was immediately picked up by Sperry’s retail network and was another instant success.
In 1939, as World War II took hold, the US War Department contracted Sperry as the official shoe of the Navy, which meant that even the dashing flyers aboard the US aircraft carriers were decked out in Sperry as they darted among the clouds. It’s said that during this time a young John F. Kennedy was wearing Top-Siders throughout his time on the PT-109 in the South Pacific. It was clear that the humble dog’s paw had revolutionised the boating world and in doing so, enabled countless sailors to return safely home.
While Paul Sperry was changing the face of sea- faring footwear, he was still working at the other family company. In 1941, he was made president of the business and he decided to let go of his side hustle. The patents for Top-Sider were sold to Uniroyal, and Paul was gifted with an oil painting of himself a s a young skipper. He remained involved in the business but the majority of his time was dedicated to Pond Lily. For the next two decades, Uniroyal continued to sell Top-Siders to both yachties and upper class tycoons, advertising extensively in boating magazines. The siped sole became a visual trademark of the brand and business marched on comfortably.
“Vacation life should consist mainly of strolling from a secluded cottage, to a pure, white beach overlooking crystal, green waters where sleek yachts and sleeker windsurfers, take turns criss-crossing the bay. It does, however, place certain demands on your shoes. Because you’ll need shoes that are as comfortable with a sandwich in a beachside bar as they are with a let in a wharfside café. Sperry’s heritage was born in places like this…”
As the 60s arrived, Sperry Top-Sider began to expand beyond the maritime market. The Canvas CVO dug its heels into the tennis world, while the young, rebellious surfing culture also took a liking to the brand’s casual canvas aesthetic. By the mid-60s, the Leather AO became fashionable on the college campus circuit. Worn with madras shorts, chinos, oxford shirts and loose-fit blazers, Sperry became the go-to brand for a new kind of casual style. The Preppy Handbook defined the well heeled lifestyle, and the Top-Sider AO was formally recognised as the definitive footwear component in the ‘preppy’ style arsenal.
The classic Top-Sider style had spread into the fertile land of popular culture, and many wanted to dress like the stars. Bob Denver’s much-loved character Gilligan shared the spotlight with his Sperrys, while legendary actor Paul Newman was often spotted wearing the CVO on deck.
In 1979, Sperry was purchased by Stride Rite Corporation, which was looking to expand their enterprise. Stride Rite widened distribution streams, building dedicated channels for classic marine shoes, casual fashion styles and the women’s line. Sperry continued to introduce technological advancements, through ongoing associations with world-championship athletes including the 1987 America’s Cup-winning skipper, Dennis Conner. They served as the official footwear sponsor of the America’s Cup as well as the official sponsor for the US Olympic sailing team for many years. To this day, Top-Siders are still the boat shoe.
Paul Sperry’s Legacy
Beyond the patented non-slip sole, Sperry contributed much more to the sport of sailing over the years. Their shoes have always been one step ahead of the game, without ever sacrificing that classic Sperry style. They’ve pioneered new techniques for tanning and treating leather to improve water resistance, breathability and durability. They’ve also gone upmarket, using premium alternatives such as elk leather, and branching out to build functional footwear for land-lubbers. At one point, the company also produced necessities for life on the sea, including foul-weather suits and rubber dinghy boats.
Paul Sperry continued to work at both Pond Lily and Top-Sider until he passed away in 1982, at the ripe old age of 87, proving what he had demonstrated so many times over the years – that he was one tough, dedicated old sea-dog. Unlike so many stories of big brands and legendary companies, Sperry Top- Sider is a humble tale. Just one very dedicated man. And a Cocker Spaniel named Prince.
– This article originally appeared in Sneaker Freaker Issue #37, pick up a copy in our web store.