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Sailing in Style: What to Wear on a Boat

The date’s set, your bags are (almost) packed, heck, the boat’s at the dock. Don’t head out of town yet, though: You’re going to need to know what to wear on a boat, and as soon as possible, at that. Take a little old-school inspiration in the form of a rugged fisherman’s sweater, throw on some tailored swim shorts, step out in boat shoes that are land and water-ready, then consider yourself geared up to hit the water in style.

After all, this is no time to pull any punches. You might meet relentless or driving winds on the water, and perhaps on the same day — there’s no excuse not to be ready to embrace whatever the high seas (or the lake, or the river!) bring your way. Our stylish picks for what to wear on a boat can help cast off the right way.

Todd Snyder x Sebago Portland Boat Shoes

Todd Snyder x Sebago Portland Boat Shoes

Let’s start with a critical first piece of gear to wear on a boat: Your boat shoes. Sebago has been making some of the best ones around for years, and they’ve now gotten an update that looks stylish on the water, and back in the city, courtesy of lauded NYC designer Todd Snyder.

Pedro and Tailor Tee  

Pedro and Tailor Tee

A T-shirt becomes more than just a T-shirt if you find the right one, and Pedro & Tailor has carefully crafted this essential tee to work more than stylish no matter where it goes (yes, on and off the boat). Made with soft, American-grown Supima cotton, it’s a tasteful and cool summer tee you can wear to grab a beer back on the mainland.

Armor-Lux Original Striped Jumper

Armor-Lux Original Striped Jumper

They don’t call it the high seas for nothing: When the water gets a bit too choppy and the breeze picks up, throw on this handsome, rugged striped jumper from an iconic brand.

Everest Isles Swimmer Short

Everest Isles Swimmer Short

Say goodbye to the baggy swim trunks you’ve (maybe) had for years. These tailored swim shorts from Everest Isles are cut as stylishly as your favorite shorts, with that crucial water-ready capability thrown in for good measure.

Howler Brothers Aguacero Jacket

Howler Brothers Aguacero Jacket

Hey, we told you it could get choppy and windy out there. Keep this functional, adventure-ready rain jacket on hand from a brand that knows a few things about the great outdoors.

Seiko Prospex Diver Watch

Seiko Prospex Diver Watch

For casual swimming and more intensive diving — and of course, a cold beer to top it all off — you need a tough dive watch that delivers the goods in terms of form and function.

Huckberry Canvas Snapback

Every guy needs a well-worn, much-loved hat with some stories to go along with it. For tales of adventure (and relaxing days) on the water, get this durable, cool-as-heck canvas snapback from Huckberry.

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