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Sperry Top-Sider 'Authentic Original' Relaxed Chukka Boot (Men)
 
Sperry Top-Sider 'Authentic Original' Relaxed Chukka Boot (Men)
Sperry Top-Sider Men's Boots: Own the Original, but with a trendier spin. American Original meets Enduring Style with this urban take on our classic silhouette.   ..Read More
Color: Black, Chestnut Leather, Black Suede   Size: 8.5m, 11.5 M (d), 10.5 M (d), 12 M (d), 11 M, 9.5 M (d) [...]  
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$82 to $120
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Sperry Cup Chukka Grey by Sperry Top Sider
 
Sperry Cup Chukka Grey by Sperry Top Sider
Sperry Cup Chukka Grey by Sperry Top Sider
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$100
Free shipping
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Sperry Men's Boots: Men's Authentic Original Chukka Boot
 
Sperry Men's Boots: Men's Authentic Original Chukka Boot
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.   ..Read More
Color: Black / Brown   Size: 11.0m  
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$100 to $101
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Sperry Men's Boots: Men's Sperry Top-Sider Boat Chukka by Made in Maine
 
Sperry Men's Boots: Men's Sperry Top-Sider Boat Chukka by Made in Maine
The Made in Maine collection of footwear is hand stitched by artisans in Maine, using U.S. sourced leather and the finest materials.
Color: Tan Leather, Brown Leather   Size: 7.0m, 8.0m  
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$390.00
Free shipping
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Sperry Women's Sedona Moccasin Boot by Jeffrey
 
Sperry Women's Sedona Moccasin Boot by Jeffrey
Sperry Top-Sider Women's Special Edition Shoes: Jeffrey Kalinsky of Jeffrey New York provides a designer twist to an American Original.   ..Read More
Color: Tan Suede, Sand Suede, Toasted Coconut Terri Suede   Size: 6 M, 7.5m, 6.0m, 9.5m  
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$99 to $130
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Sperry Top-Sider Winter Authentic Original Chukka Boots - Leather Shearling-Lined (For Men) - BROWN (12 )
 
Sperry Top-Sider Winter Authentic Original Chukka Boots - Leather Shearling-Lined ...
CLOSEOUTS .
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$98
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Sperry Top-Sider Winter Authentic Original Chukka Boots - Leather Shearling-Lined (For Men) - BROWN (7 )
 
Sperry Top-Sider Winter Authentic Original Chukka Boots - Leather Shearling-Lined ...
CLOSEOUTS .
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$98
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Sperry Top-Sider Leeward Chukka Men's Lace-up Boots
 
Sperry Top-Sider Leeward Chukka Men's Lace-up Boots
The classic style of the Leeward Chukka by Sperry Top-Sider will always bring you to the top of the class. Genuine handsewn tru-moc construction.   ..Read More
Color: Brown   Size: 10 M (d), 8 M (d), 11 M (d), 10.5 M (d), 9 M (d) [...]  
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$69.99
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Sperry Sperry Top-Sider Cloud Logo Shipyard Longshoreman Chukka Men's Coffee Leather
 
Sperry Sperry Top-Sider Cloud Logo Shipyard Longshoreman Chukka Men's Coffee Leather
Own the Original, but with a trendier spin. American Original meets Enduring Style with this urban take on our classic silhouette.
Color: Coffee Leather   Size: 11.0m  
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$60 to $90
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Sperry Mariner II ASV Lug Sole Chukka Men's Dark Brown / Olive
 
Sperry Mariner II ASV Lug Sole Chukka Men's Dark Brown / Olive
Sperry Top-Sider Men's Boots: These aren't your father's boat shoes.
Color: Dark Brown / Olive, Brown   Size: 10 M (d), 8 M (d), 7.5 M (d), 11 M (d), 10.5 M (d) [...]  
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$72 to $130
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Sperry Cloud Logo Drifter Chukka Espadrille Men's Black / White Printed Canvas
 
Sperry Cloud Logo Drifter Chukka Espadrille Men's Black / White Printed Canvas
Own the Original, but with a trendier spin. American Original meets Enduring Style with this urban take on our classic silhouette.
Color: Black / White Printed Canvas, Taupe Canvas   Size: 7.0m, 8.0m  
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$64.95
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Jeffrey for Sperry Top-Sider 'Sedona' Chukka Boot (Women)
 
Jeffrey for Sperry Top-Sider 'Sedona' Chukka Boot (Women)
Free Shipping and Free Returns Every Day!
Color: Tan Suede, Dark Brown Suede, Navy Suede   Size: 7 M, 10 M, 8.5 M, 6.5 M, 7.5 M, 11 M, 9 M, 8 M, 9.5 M [...]  
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$98.96
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Sperry Bahama Chukka Bomber Boot Men's Dark Brown
 
Sperry Bahama Chukka Bomber Boot Men's Dark Brown
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.   ..Read More
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$75
Free shipping
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Sperry Authentic Original Color Pop Chukka Boot Men's Oatmeal Leather / Citron
 
Sperry Authentic Original Color Pop Chukka Boot Men's Oatmeal Leather / Citron
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.   ..Read More
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$100
Free shipping
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Sperry Top-Sider 'Sperry Cup' Chukka Boot
 
Sperry Top-Sider 'Sperry Cup' Chukka Boot
The Cup Chukka by Sperry Top-Sider keeps your feet steady and your style smooth even when the water decides to get choppy.
Color: Black, Dark Brown, Light Peanut, Brown, Gray [...]   Size: 7 M, 10 M, 12 M, 10.5 M, 7.5 M (d), 8.5 M, 13 M, 10.5 M (d) [...]  
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$55 to $100
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Sperry Top-Sider Boat Oxford Desert Boot Men's Dress Lace-up Boots
 
Sperry Top-Sider Boat Oxford Desert Boot Men's Dress Lace-up Boots
Now you can have your cake and eat it too, the Sperry Top-Sider Boat Oxford Desert Boot takes the original and puts a trendy spin on the design. Premium leather upper material.   ..Read More
Color: Brown   Size: 8 M (d), 7.5 M (d), 11 M (d), 10.5 M (d), 11.5 M (d) [...]  
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$99.95
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Sperry Top-Sider 'Sperry Cup' Chukka Boot
 
Sperry Top-Sider 'Sperry Cup' Chukka Boot
Sperry Top-Sider Men's Boots: These aren't your father's boat shoes.
Color: Black, Dark Brown, Gray   Size: 8 M (d), 10.5 M, 7.0m, 8 M  
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$55 to $109
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Sperry Top-Sider Drifter Chukka Men's Lace-up Boots
 
Sperry Top-Sider Drifter Chukka Men's Lace-up Boots
Head out to your next adventure in total comfort and style with the Drifter Chukka boot from Sperry Top-Sider. Cotton canvas upper for better breathability and comfort.   ..Read More
Color: Black/ White Print, Taupe, Animal Print   Size: 7 M, 10 M, 12 M, 10.5 M, 7.5 M (d), 8.5 M, 13 M, 10.5 M (d) [...]  
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$52 to $65
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Sperry Top-Sider by Jeffrey 'Sedona' Chukka Boot
 
Sperry Top-Sider by Jeffrey 'Sedona' Chukka Boot
Jeffrey New York provides a designer twist to an American Original.
Color: Sand, Tan Suede, Sand Suede   Size: 7 M, 7.0m  
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$198.00
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Sperry Top-Sider Kid's A/O Chukka (Toddler/Little Kid/Big Kid)
 
Sperry Top-Sider Kid's A/O Chukka (Toddler/Little Kid/Big Kid)
Stride Rite
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$30 to $50
 
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