It's the shoe that graces the cover of The Official Preppy Handbook so the Sperry Top-Sider's preppy
The Top-Sider was invented in 1935 by Paul Sperry, a sailor who slipped on the deck of his boat one night and fell overboard into Long Island Sound.
The 1937 patent for the Sperry top-sider
Once he pulled himself back onboard and was safely back on land, Sperry began experimenting with ways to make a non-slip shoe. It turned out the answer lay with his cocker spaniel, Prince.
One cold day, inspired by Prince's ability to run nimbly over a sheet of ice and snow without slipping, Sperry used a pen knife to carve cuts into a rubber outsole that mimicked the grooves on his dog’s paws. It was the first step toward what became his patented "Razor Siping" sole.
The shoes proved to be so effective that in 1939 the U.S. Navy named them off of the military branch's official shoes, and they became the official footwear of the casual uniform of the United States Naval Academy.
Paul Sperry with his creation
Where'd the "Top-Sider" name come from? Sailors refer to the upper deck of a ship as "topside," so it's a fitting moniker for shoes that allow them to stay "topside" without slipping overboard. (Just don't confuse it with Sebago's competing Docksides, which came later.)
The line has expanded significantly since its inception, and it now comes in all kinds of colors and materials (even patent leather!). Sperry himself continued to work for the company until he died at the age of 82 in 1987.
Sperry Top-Sider, $25 and up
We'll leave you with a few vintage Sperry ads, including a couple from the World War II era, when one proclaimed, "Like other good things, they will be back after the war":
This story originally appeared on Townandcountrymag.com.
* Minor edits have been made by the