Size and fit

The Sperry women’s Sailor Shoe has a low-top profile that gives the ankles more freedom of movement. A 360-degree saddle lacing system, run by satin laces, locks the feet in with custom fitting.

Sperry Sailor Style

Looking smart, sophisticated, and laidback at the same time, the Sperry Sailor can be easily dressed up and down. Women can pair this shoe with bright-colored loose-fit jeans paired with a sleeveless shirt wrapped in a washed-blue cardigan. Then top it off with a hat or cap of choice for that casual springy or summery look. For semi-formal wear, the Sperry Sailor also compliments shorts, skirts, and dresses all too well.

The Sperry Sailor is offered in a small variety of plain colorways, in Grey, Ivory, Lilac, and Mint.

Notable Features

The Sperry Sailor Boat Shoe has a soft pastel nubuck upper, which is secured by a 360-degree lacing system with ribbon satin laces. Its non-marking rubber outsole has the famous, patented Razor-Cut Wave-Siping design that provided countless sailors sure-footed traction on wet decks. All this gives the shoe the classic Sperry look.

Sperry Sailor History

Paul Sperry produced his first Top-Sider boat shoe in the mid-1930s: the Canvas Circular Vamp Oxford. The CVO was a thing of sheer simplicity and utility. The upper was made of a single piece that wrapped the whole foot, lined with cotton for a quick dry. The rubber sole was vulcanized to the upper. Such a simple combination made for stable, comfortable footwear.

An adventurer and innovator, Sperry kept on improving the quality of the Top-Siders. He knew he could still make a more durable leather version of the shoe. So he devised a new tanning method that conditioned leather to be tough enough to sustain prolonged exposure to salt and water without crumbling to bits.

Finally, in 1937, Sperry released the leather Top-Sider, the Authentic Original (AO). It was the first shoe to have the classic moccasin toe stitching and 360-degree saddle lacing. Many sailors found the improvements to be effective. The AO was an instant success.

In the 1960s, subcultures begin to embrace the Sperry sneakers. Surfers liked their casual, laidback looks. Tennis players wore them in the courts. College students saw them as casual, pretty, and fashionable—perfect to pair with chinos, madras shorts, oxford shirts, and loose blazers. Throughout the decades, this preppy style, as it was called, hit the mainstream.

After years of making a living in the seas, the Top-Siders had evolved and successfully stepped on land. The brand continues to do so until now, innovating their designs while paying homage to the signature Sperry style.

Among the brand’s latest releases, the Sperry Sailor style is a hybrid of the classic Sperry boat shoe silhouette and a sneaker’s outsole. Its toe box takes on the elegant almond-toe shape, and instead of rawhide laces, ribbon satin laces fastened the upper, giving the Sperry brand a new, fun look.  

Additional Info

  • The shoe has a full-length Memory Foam footbed for all-day underfoot support.
  • Its upper is made of an easy-wearing “broken-in” leather, which helps the foot feel cool.

Facts / Specs

Top: Low
Inspired from: Other
Closure: Laces
Material: Leather, Rubber Sole, EVA
Colorways: White / Purple / Green / Grey / Pink / Red / Yellow / Brown
SKUs: STS83230 / STS83428 / STS83430 / STS83433 / STS83701 / STS84356 / STS84357 / STS84359 / STS85188

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Danny McLoughlin
Danny McLoughlin

Danny is a sports nut with a particular interest in football and running. He loves to watch sports as much as he loves to play. Danny was lead researcher on RunRepeat and The PFA’s report into Racial Bias in Football Commentary. His football and running research has been featured in The Guardian, BBC, New York Times and Washington Post.