Size and fit

The Sperry Top-Sider Striper II Retro is offered in men’s sizes. While Sperry did not make these shoes available in women’s sizing, women buyers can still get their hands on these. They just have to subtract one and a half sizes from their usual size to get the equivalent sizing in men’s. The sneaker’s low-top construction gives the ankles a freer range of motion.

Sperry Striper II Retro Style

The Sperry Striper II Retro is made for summertime. Its clean, laidback look matches well with a wide variety of casual clothing. Walk leisurely under the bright, sunny days with this sneaker. Men can easily pair up this sneaker with chinos, relaxed and slim-fit shorts, light denim pants, button-downs, polo shirts, and rolled-up long-sleeved shirts. On the other hand, women can dress the Sperry pair up with comfortable bright-colored shorts or short skirts for that laidback summer fashion.

The Sperry Striper II Retro is offered in four classic-looking colorways, such as light grey, navy, white, and red.

Notable Features

The Sperry Top-Sider Striper II Retro has a durable, breathable canvas upper, fastened by a traditional lace-up style with fabric laces and rust-proof eyelets. Applied with the classic Molded Wave-Siping, its lightweight and flexible non-marking outsole delivers a sure-footed grip on both wet and dry surfaces.

Sperry Striper II Retro History

One night in the Sirocco boat, everyone was asleep but Paul Sperry, who slipped off the wet deck and plunged into the sea. Luckily, he managed to grab hold of some rigging and pulled himself back up. The incident gave him an idea to make a boat shoe that didn’t slip on wet surfaces. Once back on land, Sperry worked tirelessly on his design throughout the winter of 1935.

After countless experiments on the rubber soles, Sperry still couldn’t get the grip he wanted. Needing to clear his mind, Sperry stepped out into the snow and brought along his cocker spaniel, named Prince. Sperry was watching Prince running swiftly over the sheets of the ice when another idea struck him. When Prince came back, he checked the dog’s paws, found out what he wanted, and dashed to his workshop.

With a penknife, he painstakingly carved thin lines into a thin rubber sole. He mimicked the grooves on his dog’s paws. It dramatically improved grip on wet surfaces. He soon came up with a zig-zag herringbone cut pattern. When he finally glued the hand-cut rubber sole to the base of an old shoe, his first boat shoe prototype was done.

Not long, Sperry produced the world’s first boat shoe in 1935, the Canvas Circular Vamp Oxford (CVO). It was an instant roaring success. Throughout the decades, various Sperry sneakers appeared, all of which carry the brand's signature clean, preppy style and the famous outsole that has the legendary dog grooves in it.

Now going back to their archives, the brand brought back one of their classics, which elegantly endured the test of time: the Sperry Striper II Retro. Looking simply timeless, the Sperry Striper II Retro carries on Sperry’s legacy as being a topnotch, classic footwear brand.

Additional Info

  • The sneaker has a removable cushioned footbed, which molds to the contours of the foot, giving it a custom and comfortable fit.
  • A protective heel and toe bumper are added for a more retro look.


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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.