Here in its 90th year, the boat shoe finds itself with more street cred than decades past, as cooler labels experiment with the easy-breezy footwear and old hands—like Sebago and boat-shoe inventor Sperry—riff on their bread-and-butter style.
That also means you’ve got a marina’s worth of options to choose from before you set sail on the Good Ship Boat Shoe. There’s no shortage of classics that will channel the throwback cool of JFK Jr. at his preternaturally chilled-out best—but you’ll also find upper-deck alternatives galore, like suede takes for a swank beachside wedding, chunky-soled BBQ stompers, and dainty Japanese city-strollers.
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