10 Mind-Blowing Nautical Facts You Never Knew About Your Favorite Preppy Boat Shoes Sperry

We The Pvblic

Nowadays, you see these top-siders mostly worn by these preppy looking boys who like to match it with tailored shorts and coiffed hair.

Now, what you didn’t know about the underrated pair is that it comes from a long history of a sea-faring tradition.

1. A boat, an accident and a man named Paul Sperry.


The founder of Sperry Top-Sider and lifelong sailor Paul Sperry had an unfortunate late night on Long Island Sound when he slipped and fell from the deck of his beloved cutter Sirocco. Everyone was asleep so no one could help him climb back on.

Fortunately, he got a hold of some rigging and he scrambled back on board.


After years of being the accomplished entrepreneur that he is, he was asked what helped him create the non-slip boat shoe (yes, fam, the safety sole is precisely an octopus-like tentacle which helps grip heeling, slippery decks), and he responded, “Because I fell overboard, that’s why!”

2. At the time, boating footwear materials were only either canvas uppers with some crepe rubber glued to the bottom, or shoes that had coiled rope.

Yes, friends, it was that hard to find decent kicks at the time. Crepe would usually be the preferred material but it would be slippery as heck whenever the deck was wet. Rope sole on the other hand would be slippery when it was dry. THERE IS NO IN BETWEEN. Barefoot wasn’t an option because those who try it whenever they would sail would get their toes broken.

3. Paul was inspired by Prince, his dog.

Dogs are always the answer.


One cold day in the Connecticut winter of 1935, Paul was out with Prince, his Cocker Spaniel companion to help him clear his head after he spent an hour in his makeshift workshop. He was so astonished at how his dog darted effortlessly across the frozen landscape with ease and it boggled his mind how Prince was able to stay upright.

In that moment of curiosity and inspiration, the world’s first ever boat shoe came alive.


Paul took a gum rubber sole and cut grooves into it, which aimed to mimic his furry friend’s paws. The traction increased dramatically. However when he applied pressure against a wet piece of polished metal in the same direction of the cuts in the rubber material, the rubber became slippery.

What he did was a pretty simple fix: he cut the rubber in a zig-zag herringbone pattern aka siping.


4. The first design was the Canvas Circular Vamp Oxford aka CVO.

sperry-cvo-canvas-1sperry-cvo-canvas-2The upper had a simple design which swept back to the side of the foot. It’s lined up with cotton so it’ll dry up quick asap. Sleek and classy.

5. Sperry was the official shoe of the Navy.


World War II took hold in 1939 and the US War Department contracted Sperry as the official shoe of the Navy.

6. John F. Kennedy used top-siders throughout the time of his life on the PT-109 in the South Pacific.


This meant that flyers aboard US aircraft carriers were out wearing Sperry as they came out of the clouds, including John Kennedy.

7. Uniroyal had sold top-siders to yachties and upper class tycoons showcasing comfortability.

“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…”

The patents for Top-Sider were sold to Uniroyal as Paul became president of his other family company, Pond Lily, and he decided to let go of his sideline.

In the next two decades, Top-Siders were sold to yachties and upper class tycoons as the brand of the siped sole continued to showcase comfortability.

8. The Preppy Handbook recognizes the Top-Sider AO as the definitive footwear in the ‘preppy’ ootd


And this is where these #OOTD-oriented dapper boys got it from.

9. Sperry served as the official footwear sponsor for the US Olympic sailing team.

Sperry was bought by Stride Rite Corporation in 1979 and they pretty much dedicated the classic marine shoes to casual fashion styles and for the women’s line. It became the official footwear sponsor of America’s Cup, as well as the sponsor of the US Olympic sailing team.


BONUS: Dennis Conner led the America’s Cup Team that won the trophy for the United States back in 1987.


10. Never judge a shoe by its cover. You can wear it to beaches and all your adventures!


Contrary to popular modern day belief, the Sperry top-siders are not just for show on your usual outings with your family and friends. They were built for durability, the capacity to take you to different wonders all over the world. They were built not only to help keep you upright during rainy days, but to keep you going throughout life.

You can take them anywhere with you, from the most serene beaches to the highest peak of mountains.

So yeah, Sperry pretty much accomplished all that. Remember all those little glories and the little story of how Paul created the perfect top-siders whenever you see a preppy boy wearing this world class boat shoe.

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