Boat shoes have gotten a bad reputation over the years — relegated to the same “out” category as salmon-colored shorts — but Strategist style columnist Chris Black says they’re on the upswing. (He’s often seen wearing a pair from The Row.) Plus, they’re a great transitional shoe for this not-summer-not-yet-fall weather. You can’t get more classic than Sperry, which has been in the boat-shoe business since the 1930s. And it just so happens that we’ve unearthed a shockingly good deal on a pair of quintessential Sperrys at Amazon: Originally $110, these top-siders are currently $50 in the “sahara” shade (other colors are also on sale, but they aren’t as deeply discounted). The trademarked “Original” style features hand-stitched moccasin details, laces through the sides of the heel for an adjustable fit, and rust-resistant eyelets. They’re exactly what you think of when you hear the words “boat shoe.”
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