The shoe that any summer outfit is incomplete without began its design trajectory as the greatest innovation to sailor’s footwear. Designed by Paul A. Sperry in 1935, these shoes were specifically created to withstand maritime deck conditions.

The shoes consist of a canvas or leather upper-shoe with non-marking rubber soles grooved with a siping pattern. These small grooves were actually inspired by the paws of Prince, Paul Sperry’s dog, and designed to provide extra traction on wet surfaces. 

Designed specifically for boat life, Sperrys won over their niche market, becoming the official shoe of the navy in 1939.

In the 81 years following the introduction of the Sperry Top-Sider, the shoe’s design remained fairly constant while its context began to shift. 

Soon after Sperrys beginning, Abercrombie & Fitch began distributing the shoes. However, it was only in the 1960s that the modern boat shoe truly took off in popular culture as adoring masses attempted to emulate John F. Kennedy’s effortlessly charming New England look. The shoe continued its social climb, ultimately celebrated as the exemplary shoe of the preppy style in The Official Preppy Handbook in 1980.

Today, Sperry Top-Siders have become a summer favorite — utilizing the shoe’s quintessential nautical themes to arrive at a casual, fresh look.

But whatever you do, do not wear them with socks.