Know Your Terms: Boat Shoe

Because dropping the lingo is half the fun of dressing well.

The Original: Sperry Top-Sider

In 1935, sailing aficionado Paul Sperry became unduly fascinated by the grooved pads lining his cocker spaniel’s paws, which seemed to give little “Prince” great traction on slippery surfaces. Inspired, he cut a herringbone pattern—aka “siping”—into his own rubber soles, and thus the deck shoe was born. Made with either a canvas or leather upper, Sperry’s Top-Sider became an instant hit with boaters, and in 1939 the Navy licensed the model for its mateys, solidifying its status as the off-shore shoe nonpareil. Originally distinguished by its white, non-marking sole, today’s Top-Sider (or any of the legions of boat shoes to be created in its wake) is as likely to have a black or even lime green non-marking sole—and is as likely to be found in the Gilt MANual offices as on a yacht off the Vineyard.

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  1. Jeremy says:

    curious: what looks good paired with boat shoes? additionally, are these a sock-less shoe?

  2. Christopher says:

    Jeremy, nicely tailored shorts of all varieties and chinos with a little roll look great with a boat shoe. And absolutely never ever so much as let a sock within their vicinity.

  3. Andrew says:

    I’ve been known to hide ultra-low socks under my boat shoes. Don’t tell anyone.

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