Best Boat Shoes 2021: Stylish Slip-Ons for Sailing, Walking, Fashion - Rolling Stone
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RS Recommends: The Best Boat Shoes to Upgrade Your Summer Footwear

From classics like Sperry Top-Siders to more modern renditions, these kicks are ready for any summer activity – no boat required

best men's boat shoesbest men's boat shoes

Courtesy Sperry

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Shopping for men’s shoes is a strange endeavor right now. Sneakers are everywhere from the basketball court to the office while shoes like loafers and derbies are still being worn by well-dressed gents of all ages. Throw in sandals and cowboy boots and you’ve got one confusing and extremely exciting men’s shoe world. That’s where the best men’s boat shoes come into the mix.

The best boat shoes offer an in-between option that’s dressier than a sneaker but more casual and more comfortable than a dress shoe. Despite their name, boat shoes aren’t just for boating anymore (although they’re still great for that too). You can now spot boat shoes at beaches, weddings, bars, offices and just about any summery event you can think of.

If you’re in need of some summery kicks (that also work well into fall), read on for the best boat shoes to buy right now. We’ve found several options that range from classic Sperrys to designer picks to streetwear takes on the nautical staple. Check them out below.

1. Sperry Men’s Authentic Original Leather Boat Shoe

best mens boat shoes sperry

Courtesy Sperry

At 86 years old, the Sperry Top-Sider is still one of the best boat shoes around. The shoe’s original innovations were a grooved sole that would grip the deck of a boat without leaving scuff marks, as well as a 360-degree lace-up design to keep the shoes from falling off. These features are still present, but now they lend more iconic preppy style than utility. Wear them with jeans, a button-up shirt and a sport coat on business casual occasions, or dress them down with jeans and a tee for an elevated weekend outfit.

More proof that Sperry is still king of the boat shoe market? The brand has teamed up with John Legend on a number of campaigns and collaborations over the last few years.

UPDATE: As of writing, Sperry is having a spring sale, offering 40% off select styles with code SPRING40. Click here to shop the eligible styles, and use the code at checkout to activate savings.

Buy: Sperry Original Leather Boat Shoe at $94.95

2. Sebago Dockside Portland

boat shoes sebago

Sebago is another old-school manufacturer that’s still one of the best sources for boat shoes. These Dockside Portlands are one of our favorites from the throwback brand, with a premium leather construction and quintessential boat shoe details. You get a non-marking rubber outsole, heel lacing, and a comfort upgrade in the form of a molded EVA foam insole for all-day support. The Docksides come in a variety of colors, but we think this dark navy blue and white is a nice nod to nautical style.

Buy: Sebago Dockside Portland at $139.95

3. Sperry Men’s Authentic Original Float Boat Shoe

boat shoes float sperry

Courtesy Sperry

Made using 100% buoyant EVA, these Sperry Floats are a modern version of the brand’s classic boat shoe. Because they can float and get wet, they’re really a better pick for serious boating, beach days and lounging by the pool. They’re also designed with “gills” and “portholes” all over which drain of any water while keeping your feet cool. These features make the Floats good sandal alternatives — plus they’re grippier and stay on easier than most sandals.

Buy: Sperry Authentic Original Boat Shoe at $44.95

4. Brunello Cucinelli Suede Boat Shoes

boat shoes suede designer

Courtesy Mr. Porter

If you’re looking for an upscale boat shoe worthy of replacing loafers, check out these Brunello Cucinelli slip-ons. The shoes are made in Italy using premium calfskin suede in light beige, allowing year-round usage. Although their material is non-traditional, the Cucinellis sport some classic boat shoes design notes including wrap-around laces, rubber soles and moc-toe stitching. We recommend wearing them slightly dressy with slacks or chinos and a sophisticated button-up.

Buy: Brunello Cucinelli Suede Boat Shoes at $745

5. Cole Haan ZERØGRAND Venetian Loafer

loafer boat shoes cole haan

Cole Haan

Even though these Cole Haan ZERØGRANDs are called loafers, they’re really more of a sandal-boat shoe hybrid. The shoes’ high-quality nubuck material is nicely complemented by their casual slip-on style, which lends itself well to business casual attire. They’re also extremely comfortable thanks to a thick rubber outsole and a cushioned footbed. This comfort, combined with the slip-on design, makes the kicks great for traversing airports and traveling in general.

Buy: Cole Haan ZERØGRAND Loafer at $99.95

6. Reef Deckhand 3 TX Boat Shoe

sneaker boat shoes reef


Reef is known for casual shoe-slash-sandals that can handle lounging, quick hikes (say, to the beach), traveling and boating. We’re big fans of these Reef Deckhand kicks for anyone looking to grab some casual boat shoes. With a fabric and leather upper, laces and a moc toe, the shoes have a surfing-inspired look that’s still pulled together enough for hitting the bar or restaurant. Wear them with shorts or jeans and a tee or linen shirt for a comfy, vacation-ready look.

Buy: Reef Deckhand 3 Boat Shoe at $55

7. Timberland 2-Eye Boat Shoe

leather boat shoes timberland


Though best known for rugged boots, Timberland makes some of the best boat shoes around. These two-eye boat shoes from the footwear brand feature a premium leather upper, a grippy rubber outsole, and an all-around clean look, the kicks are ready for boating and yacht club dinners. Inside, you’ll also find a supportive footbed for lasting comfort while you stand on the deck or walk around town.

Buy: Timberland 2-Eye Boat Shoe at

In This Article: Fashion, footwear, RS Recommends, Shoes


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