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The Blog from Oi Polloi presents: by Tayler Willson •

There aren’t many shoes that find themselves in the unique position the humble deck shoe finds itself in. Made for a certain type of person, but worn by all sorts of people — a shoe that’s become one of the most iconic and recognisable shoes in the world, without really even trying. It’s something to be celebrated. 

And whether you’re picturing a tired pair of sodden deck shoes that have been demoted to work wear, or a rigid box-fresh duo worn by your old man’s mate who has a jumper draped over his shoulders (and a yacht he’s almost certainly only leased for a week) - there’s a deck shoe for everyone. 

For almost fifty years though, that wasn’t the case. Casting back to the 1930s, Paul Sperry, an American sailing enthusiast, came to realise how dangerous and slippery the freshly-painted decks of a yacht were. He himself had only recently bought a second-hand schooner (the boat, not the glass) and soon found that wet decks were even worse.

Initially, he looked to give the decks a little more grip with emery dust, and while this worked, falling on it with bare skin was like cheese to a grater. This saw Sperry start to customise footwear. At the time, the espadrille was becoming popular across Europe, and while they did provide decent grip on wet decks, their rope soles - ironically - were akin to Heelys on a dry deck.

He then went for rubber-soled shoes and, thanks to his cocker spaniel companion, Prince, found himself creating the very first deck shoe. Prince’s ability to wander across slippery surfaces intrigued Sperry and lead to him designing a rubber sole based on his paw.

He called this the ‘Razor-Spiring’ design and approached the United States Rubber Company (USRC) to try and flog the idea. USRC, though, weren’t interested as they thought the design would prove too costly. Converse were keen though, and from 1935 they started to send their soles to Sperry who would cut and return them to Converse to complete the shoe. 

A mate of Sperry’s came up with the name Sperry Top-Sider for Sperry’s first shoe and convinced him to sell them at $4.50. Sperry subsequently sent over 100 handwritten letters to the iconic Cruising Club of America, to which he received a reply for each one. Soon things ramped up and word began to spread and soon enough they were given the contract for the US Navy that saw them providing all necessary footwear. 

Over the proceeding sixty-or-so years, the deck shoe was adopted by people from all walks of life, but it was in the 1980s that the shoe really began to gain traction on dry land thanks to The Official Preppy Handbook. Published in 1980 and written by Lisa Birnbach, the book of preppy gear featured a pair of deck shoes on its cover, an inclusion that cemented its place in the-then fashion.

Although an iconic shoe had been created, it did raise a question that rambles on to this day; should deck shoes be worn with, or without, socks?

A group that were firmly on the with side were the Paninaro, an iconic Italian youth subculture who came to prominence for their mint sense of style in the 1980s. The Paninaro adopted the deck shoe as a part of their extravagant rig-out, and would tend to pair them with a pair of argyle Burlington socks.

The name ‘Paninaro’ comes from the phrase “panino” which means bread in Italian; a name La Stampa - one of Italy’s biggest newspapers - branded them thanks to Al Panino, a sandwich shop in Milan, where the group used first to hangout.

Their style was very brand-specific, and the fact the deck shoe made the cut was a defining moment. Although Sperry had created the shoe, it was American Sebago that was often the Paninaro’s deck shoe of choice. Alongside the likes of CP Company, Stone Island, Versace, Best Company and Naf Naf, the deck shoe - whatever the brand - became a part of the elite. 

Fast-forward to the modern day, and the deck shoe remains a staple in many wardrobes. Whether you’re sailing the seas and definitely staying upright; or slipping on a pair on your way to five-a-side, the deck shoe remains one of the most iconic shoes of our generation.

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