They're half formal, half casual, super comfy, and totally dorky -- but you've got to love them. Something about wearing boat shoes always makes me feels ironic, like I'm mocking yacht club culture. Yet, it's really the kind of mocking that's based on jealousy, because I wish I had a giant boat too -- who doesn't? -- but class envy is only a part of the beauty of boat shoes.

Sperry's Top-siders are a totally iconic piece of preppy men's fashion, you can wear them with shorts or slacks -- and if you ever do find yourself trying to chug a beer on a slippery fiberglass boat, it doesn't hurt to have a pair.

They're the kind of shoes that can legitimately fall into both the men's fashion and gear categories, so they're kind of a double-whammy. They're super-flexible, slip resistant, and they don't mark up your boat when you slide around. Plus, I can wear them without socks and I don't look like 'white trash' -- except for the trucker hat.

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