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Douglas Harper's Etymology Dictionary
top-sider

kind of casual shoe, 1937, from topside in nautical sense of "upper deck of a ship," where the rubber soles would provide good grip; from top (n.1) + side (n.).

Usage examples of "top-sider".

He was dressed in a blue boatneck shirt, white cotton slacks, and white canvas Top-Siders.

Today, he wore his usual Hawaiian print shirt and Sperry Top-Siders with no socks but had opted for dark cargo shorts and a black armband as con-cessions to her grandmother's recent passing.

He tried to think of what Rodger Donovan had been like, striding along the Parisian boulevards in his Izod shirts, white duck trousers, and Top-Siders.

He was clad in a purple Ralph Lauren cotton polo shirt, a pair of old, smeared white ducks, and scarred Top-Siders without socks.