The History of the Deck Shoe

Humble Beginnings


In the North East of America during the 1930’s, a sailor-turned-shoemaker, Paul Sperry, was out to create something that would allow him to safely traverse the deck of any boat during rough seas with wet and slippery flooring.

The inspiration for the early design was his pet dog – a Cocker Spaniel named Prince who found running on ice easy with the grooves found on his paws.

Sperry went to work cutting the same pattern into the shoes which provide them with unparalleled grip and traction on wet flooring – perfect for boats! This new product was named the Sperry Top-Sider.


Sperry set out to provide the new sole with a patent, and offered it out to various manufacturers including the U.S. Rubber Company and Converse.

The latter accepted his offer despite it costing more than the high end shoes of the time did, at $4.50 compared to $3.75.

The soles were manufactured by Converse before sipping was done by Sperry himself and sold.


As the Deck style became more popular within sailing circles, the US Navy picked up on its influence, and purchased the right to manufacture them to all its sailors.

As a result of the increased production, Sperry sold the business to the U.S. Rubber Company which saw the product marketed to the general public – just four years after their initial rejection.


The Deck shoe became a fashion icon in the 60’s due in part to the celebrity endorsements of the time. It was commonplace to see the then president John F. Kennedy wearing them which made the nautical – cool.

Throughout the decades, the Deck shoe fell in and out of fashion – but with its timeless appeal and excellent design authenticity, the style continued to sell around the world in its numbers.

From Chatham

Deck II G2

Blue // Chestnut // Walnut


The unrivalled British-designed lace up boat shoe, Deck II is a key style in our bestselling G2 collection, which is famed for its long-lasting, high quality shoes.

Deck Lady G2

Chestnut // Walnut


The unbeatable classic Deck Lady G2 shoe. Now features an improved rubber sole unit and updated branding.

Skipper Kids

Black // Brown


Skipper Children’s Boat Shoe – just like Dad’s deck shoes. A two eyelet classic boat shoe style in our beautiful pull up leathers.