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Sperry Is Selling This Classic Boat Shoe for $50 Off. It's the Biggest Fall Fashion Flex

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The classic boat shoe is making a quiet resurgence. Deck shoes have always occupied a niche space, and lately, menswear obsessives are revisiting and embracing them. Boat shoes may not be for everyone—they don’t have the swagger of a desert boot, the elegance of a suede derby, or the charm of a moccasin. But JFK looked damn good in boat shoes, and you can, too. They have heritage, they're immensely versatile and comfortable, and they own their distinctive silhouettes unabashedly. 

If you're going to join 'em, you ought to do it right: Sperry Unisex Authentic Original 3-Eye Vibram Boat Shoes embody all of those points and take things up a notch with a rich suede upper and durable Vibram sole at a very accessible price point. These are the slyly stylish boat shoes for men that other boat shoes want to be—and they work for events and seasons you might not expect.

I spend a lot of time at market appointments, scouring the industry for garments and goods that deserve readers' attention. I’ve never been much of a boat shoe guy, but the latest iteration from Sperry, the undeniable granddaddy of the category, intrigued me. Sperry Top-Siders have been synonymous with boat shoes for decades, but this reimagined version—with its sumptuous suede upper (or leather if you prefer) and rugged Vibram sole—felt like a fresh take.

In today's landscape, there's a noticeable shift toward a more lived-in and casually elegant vibe—and these Sperry boat shoes fit right into that. Though they're available in chestnut brown leather, it's the light tan suede (you don’t see that often in boat shoes) that embodies that laid-back, artisanal feel. The first thing I noticed was just how soft the suede felt. The upper molded to my foot almost immediately, yet felt robust for protection and insulation in the cooler weather ahead. Suede is not water-friendly, so it makes sense that you don’t see them as often in shoes built for boats; maybe don't take them on your next sailing adventure, but as lifestyle wear, these are a handsome, comfortable, dependable style flex.

Best Boat Shoes for Men That Happens to Be Perfect for Fall: Sperry Unisex Authentic Original 3-Eye Vibram Boat Shoes

Sperry Unisex Authentic Original 3-Eye Vibram Boat Shoe

Courtesy Image

The thick, moccasin-type laces are substantial and stay securely tied, a welcome relief given how easily boat shoelaces can come undone. Instead of the traditional metal eyelets, they feature simple hole punches, and the 360-degree skip lace system makes for a snug fit around the top of your foot and heel. Inside, they're padded with an EVA heel cup that absorbs shock. These shoes almost have a sneaker-like comfort to them.

Traditionally, boat shoes feature rubber soles for grip. Sperry has elevated this by incorporating a Vibram lug sole. This thick rubber outsole, characterized by deep indentations, offers excellent traction for slip resistance, long-lasting wear, and stability on uneven or slippery terrain. Boat shoes typically don't feature a lug sole, as it can look too bulky, but here, the aesthetic works and adds a cool contrast in an off-white hue. While I would not recommend these shoes for serious climbing or extreme outdoor activity, the Vibram soles equip them with the traction you'll appreciate for dropping temperatures and crunching leaves, whether on light weekend hikes or city streets.

With Sperry's remarkable history, these shoes bring more than just style—they carry heritage. Throw the rugged sole into the mix, along with a buttery suede, and you've got a boat shoe built for fall. Boat shoes might not be everyone's go-to, but if you're on the fence, these are the stylish, solid choice you've been searching for. You can dress them up with khakis and a blazer, or down with jeans and a leather jacket. Sperry Unisex Authentic Original 3-Eye Vibram Boat Shoes prove that you can rock these maritime classics even in chillier months—especially when they look and feel this good.

Related: 19 Best Casual Shoes for Men to Look Sharp When Dressed Down