Yachting Shoe

AKA: boat shoes, deck shoes, topsiders

How to say it: yot-ing shoo

Traditional Features: 

Yachting Shoe

  • canvas or leather upper
  • non-marking sole with a herringbone groove pattern to provide grip
  • moccasin-like style
  • visible, durable stitching

21st Century Yachting Shoes

Yachting shoes are no longer solely the realm of boating enthusiasts; designers from the high-end to the high-street are cashing in on the constant popularity of the classic style and releasing version of the shoe in several variations that fit the brand and current trends.

Christian Louboutin Sketchers

Christian Louboutin, Sketchers

Sperry TODS

Sperry, TOD’S


…of the style: The yachting shoe was introduced by Paul Sperry in 1935. Sperry, an avid boatman, was walking his dog one day in Connecticut when he noticed that his cocker spaniel was able to run across the ice without slipping. Inspired by his dog and pattern of grooves on his paws, Sperry made herringbone-like cuts in the bottom of his sailing shoes  and manage to create a non-slip surface – the Sperry Top-sider was born.

The top-siders were a hit with fellow boaters as the white soles of the shoes not only provided traction on the slippery boat surfaces, but also didn’t mark the boat decks thanks to their white colour. However, the shoe remained somewhat of a niche product until the mid 1930s when Abercrombie and Fitch began distributing the shoes in their stores. In 1939 the US Navy recognised the benefit of the style and negotiated a deal to allow it to manufacture the shoe for it’s sailors – a practice which continues today.

With the introduction of Sail Magazine in1966, followed by the release of the Jaw’s movies sfrom 1975, the yachting shoe began to go mainstream. In 1980 the Official Preppy Handbook proclaimed the shoe to be an integral part of the Prep uniform and the style was cemented as a fashion classic.

Over the years the yachting shoe has maintained its hold on Preppy and boating style and has floated in and out of more mainstream fashion as the trends changed. Many designers regularly release the shoe in various colours and materials, playing with the classic styling to help it fit into the current fashions. It is a comfortable, versatile and easy to wear style and will no doubt maintain a stable level of popularity on the footwear market for many years to come.

…of the name: The shoe is called a ‘yachting shoe’ because it was originally designed to be worn on yachts and boats.

Random Facts

  • the first Sperry Top-siders cost $4.50
  • Paul Sperry’s dog was called Prince

For more info on Yachting Shoes try Wikipedia, Visual.ly, Gentleman’s Gazette or the Fairchild’s Dictionary of Fashion

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