Men
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Orland 2-Eye Driver
Get behind the wheel in comfort and confidence with the 2-Eye Orland Driver Loafer. Crafted from nubuck leather with moccasin construction, it features adjustable 360° Lacing™, a cushioning foam insole, and Sperry’s signature Wave-Siping™ sole for sure-footing on wet or dry surfaces. This casual,...- $33.60
$59.49- $33.60
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Authentic Original™ 2-Eye Lug Boat Shoe – Official Sperry
Inject rugged appeal into your wardrobe with Sperry’s Authentic Original™ 2-Eye Lug Sole Boat Shoe. Its nubuck upper features moccasin stitching and a 360° Lacing System™, while its sole features our famous Wave-Siping™ technology for secure footing in wet or dry conditions. This everyday...- $29.99
$52.92- $29.99
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Authentic Original™ Venetian Loafer – Official Site | Classic Slip-On Shoes
Slip into the men’s Authentic Original™ Venetian Heritage Loafer to experience the best in comfort and elevated casual style. Crafted from supple leather, it features EVA cushioning and our signature razor-cut Wave-Siping™ outsole for supreme comfort and confidence with every step. Wherever your day...- $46.20
$87.06- $46.20
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Newman Chukka Boot II
- $35.98
$63.71- $35.98
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Men's 4-Pack Boot Socks
- $9.75
$14.61- $9.75
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Ventura Sandal
Destined to become your favorite warm weather shoe, make sure the Ventura Sandal is part of your wardrobe. Its cushioned footbed ensures ultimate comfort while its quick on and off design delivers ease of wear. Plus, with its molded Wave-Siping™ sole, you can be...- $12.99
$19.51- $12.99
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Helm 2 Eye Sneaker – Official Brand Name | Product Keywords
- $27.49
$45.77- $27.49
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Sperry x Todd Snyder x Mister Rogers' Neighborhood CVO Sneaker Reissue
Inspired by Mister Rogers’ enduring warmth and approachability to American style, the Sperry x Todd Snyder x Mister Rogers Neighborhood collaboration reimagines Top-Siders through a nostalgic lens. First introduced in 1935 and made iconic by figures like Mister Rogers, the 70s re-issue CVO comes...- $48.00
$88.73- $48.00
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Authentic Original™ Made in Maine 2-Eye Boat Shoe
Handcrafted by masters of their craft using the highest attention to detail, the Made in Maine Authentic Original™ 2-Eye Boat Shoe represents the pinnacle of luxury. Wave-Siping™ technnology provides grip on wet and dry surfaces and 360° Lacing™ ensures a custom fit. Crafted with...- $110.60
$322.37- $110.60
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Authentic Original™ 2-Eye Lug Boat Shoe – Official Sperry
Inject rugged appeal into your wardrobe with Sperry’s Authentic Original™ 2-Eye Lug Sole Boat Shoe. Its nubuck upper features moccasin stitching and a 360° Lacing System™, while its sole features our famous Wave-Siping™ technology for secure footing in wet or dry conditions. This everyday...- $29.99
$53.32- $29.99
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Gold Cup™ Authentic Original™ 2-Eye Boat Shoe
The Gold Cup Authentic Original™ 2-Eye Boat Shoe was created for those who cherish the finer things in life. Uniting premium leather with our signature 360° Lacing System™ and our famous razor-cut Wave-Siping™ outsole, the result is a shoe that gets better with time...- $68.25
$138.09- $68.25
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Men's 6-Pack Liner Socks
Built to keep you comfortable from morning to night, these socks pair moisture-wicking fabric with cushioned support for all-day wear. Whether you're breaking in new boat shoes or layering up for cooler days, they add just the right touch of warmth and style. A...- $9.75
$14.37- $9.75
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Davenport Venetian Driver
Slip into a timeless classic style with the Davenport Venetian Loafer. Flaunting unlined full-grain leather upper, a podded rubber outsole, and Adaptive Wave-Siping™ technologies, you can stay comfortable, grounded, and stylish all day long. Our signature loafer silhouette.- $44.98
$82.85- $44.98
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Gold Cup™ Authentic Original™ 2-Eye Boat Shoe – Classic Men's Leather Boat Shoes
Our original boat shoe, handcrafted with luxurious materials and unrivalled attention to detail. The Gold Cup Authentic Original 2-Eye Boat Shoe represents the pinnacle of a tradition stretching back nine decades. Crafted from premium pebble leather with lambskin lining, these boat shoes feature our...- $68.25
$138.74- $68.25
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Gold Cup™ CVO Sneaker – Official Brand Name & Product Keywords
A classic style icon is raised to the gold standard in this Gold Cup™ CVO Lace-Up. Made from the supplest leather using masterful craftsmanship, and featuring Wave-Siping™ for a solid grip and a removable insole for ultimate comfort, Sperry’s beloved sneaker silhouette is poised...- $57.75
$117.70- $57.75
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CVO Sneaker Reissue
Some shoes follow trends. This one started them. The CVO Reissue Lace-Up is a faithful recreation of Paul Sperry's iconic Circular Vamp Oxford — originally designed in the 1935s and still turning heads today. Built on a canvas upper with a memory foam lining,...- $40.50
$73.92- $40.50
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Billfish™ 3-Eye Boat Shoe – Classic Nautical Style & Comfort
A sporty, modern take on our iconic boat shoe, the Billfish is equipped to handle everything life–and the sea–throws at you. These reimagined boat shoes are made with luxurious nubuck, mesh panelling and our classic moccasin stitching, with a full-length cushioned midsole and a...- $35.98
$64.13- $35.98
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Men's 3-Pack Ankle Socks
Built to keep you comfortable from morning to night, these socks pair moisture-wicking fabric with cushioned support for all-day wear. Whether you're breaking in new boat shoes or layering up for cooler days, they add just the right touch of warmth and style. A...- $8.45
$12.74- $8.45
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Helm 2 Eye Sneaker – Official Brand Name | Product Keywords
A boat shoe with a sneaker sensibility, the Helm 2-Eye is ready to join you on all your outings. Designed with supreme comfort and casual style in mind, this twill lace-up shoe features 360° Lacing™ for an adjustable fit and a molded Wave-Siping™ outsole...- $40.50
$74.32- $40.50
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Harpoon 3-Eye Boat Shoe
The men’s Harpoon Lace-Up is a modern, sporty take on our iconic boat shoe. Built for comfort, it features a breathable mixed material upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes...- $21.99
$36.55- $21.99
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Authentic Original™ Cloud Boat Shoe
Let your shoes make a statement of your great taste and impeccable standards with this Cloud Authentic Original™ Lux Boat Shoe. Crafted from exquisitely unique materials, and with Sperry’s signature comfort features including EVA cushioning, 360° Lacing™ and a razor-cut Wave-Siping™ sole, this high-end...- $27.49
$45.91- $27.49
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Maritime Sneaker – Official Site | Shop Now
- $27.49
$45.62- $27.49
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CVO Sneaker Reissue – Official Site
Some shoes follow trends. This one started them. The CVO Reissue Lace-Up is a faithful recreation of Paul Sperry's iconic Circular Vamp Oxford — originally designed in the 1935s and still turning heads today. Built on a canvas upper with a memory foam lining,...- $40.50
$75.33- $40.50
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Dipsail Mesh 3 Eye Boat Sneaker – Official Site
- $27.49
$45.63- $27.49
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Men's 3-Pack No-Show Socks
Built to keep you comfortable from morning to night, these socks pair moisture-wicking fabric with cushioned support for all-day wear. Whether you're breaking in new boat shoes or layering up for cooler days, they add just the right touch of warmth and style. A...- $4.54
$6.84- $4.54
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Gold Cup™ Authentic Original™ 1-Eye Boat Shoe – Classic Men's Leather Boat Shoe
- $60.00
$110.40- $60.00
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Porto Flip Flop
Step into comfort with the Porto sandals. These mens' sandals feature a padded thong strap for superior comfort with a cork footbed that offers natural breathability and cushioning. The rubber sole is equipped with Wave-Siping™ technology for added traction on wet surfaces.- $8.44
$12.84- $8.44
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Helm 2 Eye Sneaker – Official Brand Name | Product Keywords
A boat shoe with a sneaker sensibility, the Helm 2-Eye is ready to join you on all your outings. Designed with supreme comfort and casual style in mind, this twill lace-up shoe features 360° Lacing™ for an adjustable fit and a molded Wave-Siping™ outsole...- $40.50
$74.76- $40.50
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Authentic Original™ 2-Eye Boat Shoe – Official Site | Classic Style & Premium Comfort
Our most iconic silhouette, the Authentic Original™ 2-Eye Boat Shoe stands out for its superior craftsmanship and attention to detail. It features traditional moccasin construction, 360° Lacing™ for a snug fit, EVA cushioning for ultimate comfort and our famous razor-cut Wave-Siping™ outsole for stability...- $46.20
$87.55- $46.20
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Sperry x Todd Snyder x Mister Rogers' Neighborhood CVO Sneaker Reissue – Official Sperry Collaboration
Inspired by Mister Rogers’ enduring warmth and approachability to American style, the Sperry x Todd Snyder x Mister Rogers Neighborhood collaboration reimagines Top-Siders through a nostalgic lens. First introduced in 1935 and made iconic by figures like Mister Rogers, the 70s re-issue CVO comes...- $48.00
$87.61- $48.00
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