Sperry Top-Sider Men's (13,569 RESULTS)

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in...
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Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 11.5M Men's Shoes

Sperry Top-Sider Dockyard Sport...

Sperry Top-Sider
Sperry Top-Sider
$130.00 $99.99

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Sperry Top-Sider Men's Authentic Original 2-Eye Sahara Shoes - 0197640
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Sperry Top-Sider Men's Authentic Original 2-Eye Sahara Shoes, Size 8 W - 0197640

Sperry Top-Sider Men's Authentic...

TheShoeMart
Sperry Top-Sider
$87.95
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Have a comfortable day walking around in these handsewn Leeward 2-Eye Moccasins by Sperry. Not only are they fashionable but they are also comfort your feet with a shock absorbing EVA heel...
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Men's Sperry Top-Sider Leeward 2-Eye - Sahara Lace Up Shoes

Men's Sperry Top-Sider Leeward 2-Eye...

Shoebuy.com
Sperry Top-Sider
$77.95
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Free Shipping Both Ways! A unique balance of comfort and good looks. These lightweight shoes are packed with rugged features and a sporty, casual style. Full grain, oil-tanned leather upper...
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Sperry Top-Sider Santa Cruz Thong Men's Sandals

Sperry Top-Sider Santa Cruz Thong...

Zappos.com
Sperry Top-Sider
$54.95
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Weathered leather is formed into a handsome one-eye boat shoe laced with contrast rawhide and featuring a wave-siped sole for traction. Color(s): dark brown, grey, navy. Brand: Sperry... Men's Sperry Top-Sider 'Authentic Original' Boat Shoe

Men's Sperry Top-Sider 'Authentic...

Nordstrom
Sperry Top-Sider
$89.95
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Free Shipping Both Ways! The Sperry Top-Sider Avenue Duck Toggle shoe makes sure you are prepared to stay stylishly cozy when the weather turns wet and cold. Stain and water-resistant...
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Sperry Top-Sider Avenue Duck Toggle Men's Slip on Shoes

Sperry Top-Sider Avenue Duck Toggle...

Zappos.com
Sperry Top-Sider
$95.00
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Sperry Top-Sider Men's Halyard 2-Eye SW Chocolate Shoes - 0777867
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Sperry Top-Sider Men's Halyard 2-Eye SW Chocolate Shoes, Size 14 M - 0777867

Sperry Top-Sider Men's Halyard 2-Eye...

TheShoeMart
Sperry Top-Sider
$59.95
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Durable boat shoe features nylon mesh quarter panels and a padded tongue for comfort and breathability. Superior foot support and stability features enhance the fit. Color(s): dark tan, off...
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Men's Sperry Top-Sider 'Billfish' Boat Shoe

Men's Sperry Top-Sider 'Billfish'...

Nordstrom
Sperry Top-Sider
$99.95
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Free Shipping on all orders! Please keep in mind there may be some color transfer after first use. This is normal. Whether it's the work week or weekend, these classic slip-ons fit the... Sperry Top-Sider Tremont Kiltie Tassel Men's Slip on Shoes

Sperry Top-Sider Tremont Kiltie...

6pm.com
Sperry Top-Sider
$90.00 $62.99
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With a stain and water resistant leather uppers, the Lanyard 2-Eye is the ideal for walking around the beach. Featuring a shock absorbing EVA heel and an air mesh and perfed upper panels,...
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Men's Sperry Top-Sider Lanyard 2-Eye - Linen Lace Up Shoes

Men's Sperry Top-Sider Lanyard 2-Eye...

Shoebuy.com
Sperry Top-Sider
$79.95
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Free Shipping on all orders! Walk into the waves of soothing comfort and never emerge with the Sperry Top-Sider Halyard 2-Eye boat shoe. Distressed canvas upper with stitch detailing along...
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Sperry Top-Sider Halyard Two-Tone Men's Shoes

Sperry Top-Sider Halyard Two-Tone...

6pm.com
Sperry Top-Sider
$60.00 $32.99
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The iconic boat shoe elevates style to the next level as part of the Gold Cup Collection. Their finely tooled premium leather uppers are sewn by hand and lined with luxuriously soft...
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Sperry Top-Sider Gold Cup Authentic Original 2-Eye Boat Shoe Tan/BrownLeather, Size 8W Men's Shoes

Sperry Top-Sider Gold Cup Authentic...

Sperry Top-Sider
Sperry Top-Sider
$150.00 $114.99
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These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in...
  •  
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 10.5M Men's Shoes

Sperry Top-Sider Dockyard Sport...

Sperry Top-Sider
Sperry Top-Sider
$130.00 $99.99

Added to Favorites

These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in...
  •  
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 8M Men's Shoes

Sperry Top-Sider Dockyard Sport...

Sperry Top-Sider
Sperry Top-Sider
$130.00 $99.99

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In 1935 Paul Sperry invented the first sailing shoe, and we've been busy re-inventing it ever since! We work with the US Sailing Team to be sure we design shoes for even the most extreme...
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Sperry Top-Sider Sea Kite Sneaker Gray, Size 10M Men's Shoes

Sperry Top-Sider Sea Kite Sneaker...

Sperry Top-Sider
Sperry Top-Sider
$80.00 $59.99

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Purchase a Gift CardHaving trouble finding the perfect size? Send a Gift Card - the perfect fit!Gift cards can only be shipped within the United States and be redeemed online at...
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Sperry Top-Sider Sperry Gift Card e-GiftCard, Size

Sperry Top-Sider Sperry Gift Card...

Sperry Top-Sider
Sperry Top-Sider
$100.00
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Jeffrey New York provides a designer twist to an American Original. Sperry's iconic silhouette paired with Jeffrey's signature flare has lead to a fashion forward collection that's sure to...
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Sperry Top-Sider CVO Slip-On Sneaker by Jeffrey CobaltBluePonyHair, Size 10M Men's Shoes

Sperry Top-Sider CVO Slip-On Sneaker...

Sperry Top-Sider
Sperry Top-Sider
$150.00
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Slip on a dress casual style and be prepared to make a statement. Built from a heritage brand, Sperry designs emanate smartness while maintaining durable comfort. Classic comfort and...
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Sperry Top-Sider Tremont Kiltie Tassel Loafer Amaretto, Size 11.5M Men's Shoes

Sperry Top-Sider Tremont Kiltie...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

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Slip on a dress casual style and be prepared to make a statement. Built from a heritage brand, Sperry designs emanate smartness while maintaining durable comfort. Classic comfort and...
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Sperry Top-Sider Tremont Kiltie Tassel Loafer Amaretto, Size 10.5W Men's Shoes

Sperry Top-Sider Tremont Kiltie...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

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These aren't your father's boat shoes. The original Sperry silhouette adapted for a more urban feel, our Chukkas are made to appease the trendy and style savvy guy. For the ultimate in...
  •  
Sperry Top-Sider Dockyard Sport Chukka Boot DarkBrown, Size 11M Men's Shoes

Sperry Top-Sider Dockyard Sport...

Sperry Top-Sider
Sperry Top-Sider
$130.00 $99.99

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The classic winter boot is now styled to the next level as part of the Gold Cup Collection. The Gold Bay Boot features premium seam-sealed waterproof leather uppers and are lined with...
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Sperry Top-Sider Gold Cup Gold Bay Boot DarkBrown, Size 10M Men's Shoes

Sperry Top-Sider Gold Cup Gold Bay...

Sperry Top-Sider
Sperry Top-Sider
$250.00 $179.99
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Slip on a dress casual style and be prepared to make a statement. Built from a heritage brand, Sperry designs emanate smartness while maintaining durable comfort. Classic comfort and...
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Sperry Top-Sider Tremont Kiltie Tassel Loafer Amaretto, Size 9.5W Men's Shoes

Sperry Top-Sider Tremont Kiltie...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

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Finely crafted traditional wing tip oxfords with brogue details take on a modern vibe with contrasting outsoles and laces. The Gold Cup Collection features premium hand-sewn leather uppers...
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Sperry Top-Sider Gold Cup Bellingham ASV Wingtip Oxford Brown/Ivory/TaupeLeather, Size 12M Men's Shoes

Sperry Top-Sider Gold Cup Bellingham...

Sperry Top-Sider
Sperry Top-Sider
$180.00 $134.99
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Purchase a Gift CardHaving trouble finding the perfect size? Send a Gift Card - the perfect fit!Gift cards can only be shipped within the United States and be redeemed online at...
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Sperry Top-Sider Sperry Gift Card e-GiftCard, Size

Sperry Top-Sider Sperry Gift Card...

Sperry Top-Sider
Sperry Top-Sider
$75.00

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In 1935, Paul Sperry invented the boat shoe. 75 years later our American Originals have been infused with 21st century fashion. The result: the Authentic Original collection. Classic...
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Sperry Top-Sider Authentic Original Suede Boat Shoe Green, Size 9.5M Men's Shoes

Sperry Top-Sider Authentic Original...

Sperry Top-Sider
Sperry Top-Sider
$88.00

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The Made in Maine collection of footwear is hand stitched by artisans in Maine, using U.S. sourced leather and the finest materials. Handcrafted with a commitment to quality, Sperry...
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Sperry Top-Sider Authentic Original Boat Shoe by Made in Maine MahoganyLeather, Size 11.5M Men's Shoes

Sperry Top-Sider Authentic Original...

Sperry Top-Sider
Sperry Top-Sider
$250.00
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These Authentic Original Leather 1-Eye Boat Shoes feature a classic silhouette with an updated trendy twist. Whether you are on board or on shore, these shoes will be sure to make waves.
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Sperry Top-Sider Authentic Original Two-Tone 2-Eye Boat Shoe Burgundy/Tan, Size 8.5M Men's Shoes

Sperry Top-Sider Authentic Original...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

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Slip on a dress casual style and be prepared to make a statement. Built from a heritage brand, Sperry designs emanate smartness while maintaining durable comfort. Classic comfort and...
  •  
Sperry Top-Sider Tremont Kiltie Tassel Loafer Amaretto, Size 12M Men's Shoes

Sperry Top-Sider Tremont Kiltie...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

Added to Favorites

Slip on a dress casual style and be prepared to make a statement. Built from a heritage brand, Sperry designs emanate smartness while maintaining durable comfort. Classic comfort and...
  •  
Sperry Top-Sider Tremont Kiltie Tassel Loafer Amaretto, Size 8.5M Men's Shoes

Sperry Top-Sider Tremont Kiltie...

Sperry Top-Sider
Sperry Top-Sider
$90.00 $69.99

Added to Favorites