Straight classic! The Sperry Top-Sider Original is quite possibly the best boat shoe ever constructed. First made in 1935, Sperrys have only recently become a mainstay among the style cognoscente. Handsewn with genuine leather, they're ridiculously comfortable and highly versatile. Whether you're ON A BOAT! or cold lampin' at a clam bake, Sperry's retro-nautical design looks on-point in nearly any setting. Retire those $2 flip-flops and rock a pair of Sperrys instead. Bonus: they also come in a variety of colors and materials. ($64.95) Buy it now
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