Most Comfortable Boat Shoes from Sperry

Sperry knows that comfort is just as important as style when it comes to boat shoes. A great option for casual days by the water or a night out on the town, boat shoes are a comfortable footwear choice when you’re looking to add some nautical-inspired flair to any look.

First, the Authentic Original™ Boat Shoe
Available in men’s and women’s sizes, our Authentic Original has defined coastal style for decades. The secret to this iconic style’s comfort? The premium leather upper and moccasin construction literally wrap around your feet. The upper of the Authentic Original™ boat shoe is made from one piece of leather that goes under your foot and then is pulled up and hand-stitched to an upper piece to create the iconic moccasin toe look. As you wear the shoe, the leather underfoot molds to your foot shape, creating a comfortable boat shoe that’s authentically yours.

Women’s Authentic Original™ boat shoe
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Men’s Authentic Original™ boat shoe
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Read on to learn more about our most comfortable women’s boat shoes and our most comfortable men’s boat shoes.

Sperry’s most comfortable boat shoes for women
Women’s Authentic Original™ PLUSHWAVE™ 2.0 Boat Shoe
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This take on our Authentic Original™ boat shoe updates the icon with increased comfort features including PLUSHWAVE™ technology and a shock-absorbing EVA heel cup. Our PLUSHWAVE™ technology is a memory foam-like material that allows for enhanced comfort with every step. While we consider any boat shoe with PLUSHWAVE™ technology the most comfortable boat shoe, this is one of the most comfortable boat shoes for walking due to its shock-absorbing and memory foam qualities. Additionally, this boat shoe has super soft laces that allow for a more secure tie, and pops of color at the heel and inside the footbed add a fresh visual flourish.

Women’s Starfish Boat Shoe
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A lower profile with a single eyelet elevates this more streamlined take on the iconic Sperry boat shoe. The combination of a handsewn moccasin construction and a shock-absorbing heel cup guarantee all-day comfort, while the rawhide laces complete the classic look. With these comfort features, the Starfish is a comfortable boat shoe option that goes great with any look.

Women’s Freshfish Boat Shoe
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This sleek, tonal take on our iconic silhouette is as comfortable as it is stylish. The Freshfish Boat Shoe is made with premium leather and flaunts metallic details and fixed cross-over laces. With the addition of our signature PLUSHWAVE™ technology and a slightly wider moccasin construction, this shoe provides superior, lightweight comfort for all-day wear.

Women’s Gold Cup™ Authentic Original™ Montana Boat Shoe
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The highest quality materials meet elevated style in the Gold Cup™ Authentic Original™ Montana boat shoe. Its upper is made from premium, full-grain leather and its rich lambskin linings cradle the foot. A cushioned heel cup reduces the shock of every step while an Ortholite® insert delivers all-day comfort. Easily one of the most comfortable women’s boat shoes, this elevated style is the ultimate choice for a luxury nautical shoe.

Sperry’s most comfortable boat shoes for men
Men’s Billfish™ 3-Eye Boat Shoe
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Classic style inspired by sport vibes. Made with full-grain leather and perforated side panels, the Billfish™ 3-Eye boat shoe gives you the comfort and support of a sneaker with the stylings of a boat shoe. Featuring full-length cushioning along the footbed for all-day support, this comfortable men’s boat shoe is perfect for a day on your feet.

Men’s Gold Cup™ Authentic Original™ Rivingston Boat Shoe
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Boat shoe? More like a yacht shoe, if we’re talking swag factor and comfort! This luxurious take on our classic boat shoe features an ultra-soft lambskin lining and next-level cushioning underfoot, thanks to the shock-absorbing heel cup and Ortholite® insole. Every feature in this shoe has an elevated look and feel—from the ultra-high-end materials to the last eyelet. When you’re ready to splurge on a comfortable boat shoe, look no further than the Gold Cup™ Authentic Original™ Rivingston boat shoe.

Men’s Sea Kite Sport Moc Boat Shoe
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Our original leather boat shoe meets our performance water sneaker. The Sea Kite Moc is durable, comfortable, and always ready to set sail. Its molded EVA midsole minimizes the impact of the sea (or the pavement) and provides cushioning and shock absorption all day long. Featuring full-grain leather and a handsewn construction, you’ll love the look as much as the feel of this comfortable boat shoe style.

Men’s Mako Canoe Moc Boat Shoe
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Our signature silhouette has been updated for versatility and comfort. Featuring rich, full-grain leather uppers in a classic boat shoe moccasin construction, the Mako 2-Eye boat shoe flaunts a padded tongue and shock-absorbing heel cup for enhanced comfort in timeless classic style. The full-length cushioning ensures all-day comfort while the molded Wave-Siping™ technology enhances traction for a comfortable boat shoe with a stable tread.

Men’s Authentic Original™ PLUSHWAVE™ 2.0 Boat Shoe
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Our Authentic Original™ Boat Shoe gets a fresh update with max comfort. Featuring our signature PLUSHWAVE™ technology, this style feels as light-as-air and provides ultra-cushioning. And made with full-grain leather, it keeps its classic nautical look but flaunts a pop of color on the heel. Easily our best boat shoe for walking, this style is just as chic as it is comfortable.

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