Best Seller
Cole Haan Men's Ogden Stitch Chukka II Boot, Woodbury/Tortoise Leather, 7 Medium US

Cole Haan Men's Ogden Stitch Chukka II Boot, Woodbury/Tortoise Leather, 7 Medium US

Always keep the classics close to you with this great chukka that is great for the winter time more

$129.06

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Cole Haan Men's Graydon Chukka Boot, Black, 7 M US

Cole Haan Men's Graydon Chukka Boot, Black, 7 M US

Cole haan graydon chukka, the fusion of casual style with engineered technology to deliver fashionable comfort. more

$94.99

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Best Seller
Cole Haan Men's Orson Chukka Boot,Milkshake,10 M US

Cole Haan Men's Orson Chukka Boot,Milkshake,10 M US

Lace up front with blind eyelets. Chukka boot silhouette. Leather and synthetic lining. Synthetic insole. Durable man-made outsole. more

$188.00

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Cole Haan Men's Zerogrand STICHOUT Chukka Boot, Black Waxy/White, 7 Medium US

Cole Haan Men's Zerogrand STICHOUT Chukka Boot, Black Waxy/White, 7 Medium US

Crafted in rich oily leather and featuring stitch out construction that harks back to old-school chukka craftsmanship prevalent among heritage shoemakers, our latest ZERØGRAND reinvention features an extra layer in its EVA midsole for added comfort and... more

$112.99

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Cole Haan Men's Cranston Chukka Boot, Woodbury Tumble, 12 M US

Cole Haan Men's Cranston Chukka Boot, Woodbury Tumble, 12 M US

Cole haan cranston boot - the intersection of rugged maine inspired casual boots with grand.os technology. more

$230.01

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Cole Haan Men's Grand Tour Chukka Boot, Desert Taupe Suede/Ivory, 10.5 M US

Cole Haan Men's Grand Tour Chukka Boot, Desert Taupe Suede/Ivory, 10.5 M US

Cole haan grand tour - the fusion of style and engineering for enhanced comfort for your casual to dress needs. more

$128.41

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Cole Haan Men's Graydon Chukka Boot, Harvest Brown, 8.5 M US

Cole Haan Men's Graydon Chukka Boot, Harvest Brown, 8.5 M US

Cole haan graydon chukka, the fusion of casual style with engineered technology to deliver fashionable comfort. more

$147.39

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Cole Haan Men's Kennedy Grand Chukka II Boot, Black, 8.5 Medium US

Cole Haan Men's Kennedy Grand Chukka II Boot, Black, 8.5 Medium US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot. more

$170.00

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Cole Haan Men's Kennedy Grand Chukka II Boot, Black, 11.5 Medium US

Cole Haan Men's Kennedy Grand Chukka II Boot, Black, 11.5 Medium US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot. more

$147.92

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Cole Haan Men's Zerogrand STICHOUT Chukka Boot, Java Leather/Dark Roast, 10 Medium US

Cole Haan Men's Zerogrand STICHOUT Chukka Boot, Java Leather/Dark Roast, 10 Medium US

Crafted in rich oily leather and featuring stitch out construction that harks back to old-school chukka craftsmanship prevalent among heritage shoemakers, our latest zerogrand reinvention features an extra layer in its EVA midsole for added comfort and... more

$280.00

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Cole Haan Men's GRANTLAND Chukka WP Boot, Java, 10.5 Medium US

Cole Haan Men's GRANTLAND Chukka WP Boot, Java, 10.5 Medium US

Cole Haan grantland boot; the intersection of rugged, maine inspired casual boots with grand.Os technology. more

$278.12

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Cole Haan Men's Kennedy Grand Chukka II Boot, Mahogany, 9.5 Medium US

Cole Haan Men's Kennedy Grand Chukka II Boot, Mahogany, 9.5 Medium US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot. more

$170.00

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Cole Haan Men's Grand Tour Chukka Boot, Midnight Grey Suede/Magnet, 7 Medium US

Cole Haan Men's Grand Tour Chukka Boot, Midnight Grey Suede/Magnet, 7 Medium US

Cole Haan grand tour - the fusion of style and engineering for enhanced comfort for your casual to dress needs. more

$120.00

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Cole Haan Men's GRANTLAND Plain Toe LACE UP WP Fashion Boot, Black, 8 Medium US

Cole Haan Men's GRANTLAND Plain Toe LACE UP WP Fashion Boot, Black, 8 Medium US

Cole Haan grantland boot; the intersection of rugged, maine inspired casual boots with grand.Os technology. more

$87.99

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Cole Haan Men's GRANDEXPLORE MOC Toe Boot WP Hiking, Chestnut/Buffalo Plaid, 9.5 Medium US

Cole Haan Men's GRANDEXPLORE MOC Toe Boot WP Hiking, Chestnut/Buffalo Plaid, 9.5 Medium US

The grand explore moc toe boot brings the element of fashion infused with the rugged outdoor element for hiking. more

$250.00

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Cole Haan Men's Keaton Moc Toe Bit WP II Fashion Boot, Woodbury WP, 7.5 Medium US

Cole Haan Men's Keaton Moc Toe Bit WP II Fashion Boot, Woodbury WP, 7.5 Medium US

Keaton moc toe bit boot with waterproof leather and suede upper. Rubber lugged outsole. Leather lining. Lace up closure. more

$200.00

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Cole Haan Men's Williams WELT Chukka II Boot, Driftwood, 8 Medium US

Cole Haan Men's Williams WELT Chukka II Boot, Driftwood, 8 Medium US

Williams welt chukka is not your average boot by any measure with its rich colors and progressive design which can be hooked up with jeans for a night on the town. more

$159.79

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Cole Haan Men's Grand Explore All-Terrain OX Hiking Boot, Black Leather/Ironstone/Magnet wp, 10 Medium US

Cole Haan Men's Grand Explore All-Terrain OX Hiking Boot, Black Leather/Ironstone/Magnet wp, 10 Medium US

An all-terrain boot that is waterproof and can face any weather element (rain or shine). more

$250.00

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Cole Haan Men's Dumont Grand Chelsea WP Boot, muir Nubuck, 8.5 Medium US

Cole Haan Men's Dumont Grand Chelsea WP Boot, muir Nubuck, 8.5 Medium US

Elegant chelsea that is waterproof but still has a classic and timeless look. more

$231.07

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Cole Haan Men's Pinch Weekender Chukka Boot, woodbury suede, 7.5 Medium US

Cole Haan Men's Pinch Weekender Chukka Boot, woodbury suede, 7.5 Medium US

A pinch weekender chukka that everybody is looking from Cole Haan. more

$123.83

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Cole Haan Men's Original Grand Chukka Boot, Woodbury/Ivory, 9.5 M US

Cole Haan Men's Original Grand Chukka Boot, Woodbury/Ivory, 9.5 M US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$180.00

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Cole Haan Men's Original Grand Chukka Boot, Black, 11.5 M US

Cole Haan Men's Original Grand Chukka Boot, Black, 11.5 M US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$179.82

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Cole Haan Men's Original Grand Chukka Boot Black, 14 M US

Cole Haan Men's Original Grand Chukka Boot Black, 14 M US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$179.82

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Cole Haan Men's Original Grand Chukka Boot, Woodbury/Ivory, 7 W US

Cole Haan Men's Original Grand Chukka Boot, Woodbury/Ivory, 7 W US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$180.00

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Cole Haan Men's Original Grand Chukka Boot, Black, 16 M US

Cole Haan Men's Original Grand Chukka Boot, Black, 16 M US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$179.82

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Cole Haan Men's Original Grand Chukka Boot, Woodbury/Dark Roast, 7 W US

Cole Haan Men's Original Grand Chukka Boot, Woodbury/Dark Roast, 7 W US

You need to buy the Original Grand Chukka to complement your Original Grand Shortwing. more

$179.93

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Cole Haan Men's Ripley Grand Chukka Boot Fashion, Cognac, 7 M US

Cole Haan Men's Ripley Grand Chukka Boot Fashion, Cognac, 7 M US

A low profile rugged outsole that keeps your foot close to the ground using our proprietary elements of our grand.Os technology. more

$190.00

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Cole Haan Men's Ripley Grand Chukka Boot Fashion, Black, 11 M US

Cole Haan Men's Ripley Grand Chukka Boot Fashion, Black, 11 M US

A low profile rugged outsole that keeps your foot close to the ground using our proprietary elements of our grand.Os technology. more

$190.00

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Cole Haan Men's Bernard Chelsea Boot Black, 9 M US

Cole Haan Men's Bernard Chelsea Boot Black, 9 M US

You just can not beat the price on the bernard using Cole Haan grand.Os technology in the footbed plus a signature puck for optimal energy return and cushioning. more

$150.00

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Cole Haan Men's Kennedy Grand Chelsea Waterproof Boot, Dogwood Nubuck wp, 7.5 M US

Cole Haan Men's Kennedy Grand Chelsea Waterproof Boot, Dogwood Nubuck wp, 7.5 M US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot) plus now waterproof. more

$200.00

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Cole Haan Men's Bernard Chelsea Boot, Chestnut/Black, 8 M US

Cole Haan Men's Bernard Chelsea Boot, Chestnut/Black, 8 M US

You just can not beat the price on the bernard using Cole Haan grand.Os technology in the footbed plus a signature puck for optimal energy return and cushioning. more

$150.00

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Cole Haan Men's Bernard Chelsea Boot Black, 13 M US

Cole Haan Men's Bernard Chelsea Boot Black, 13 M US

You just can not beat the price on the bernard using Cole Haan grand.Os technology in the footbed plus a signature puck for optimal energy return and cushioning. more

$150.00

FREE shipping

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Cole Haan Men's Kennedy Grand Chelsea Waterproof Boot, Dogwood Nubuck wp, 13 M US

Cole Haan Men's Kennedy Grand Chelsea Waterproof Boot, Dogwood Nubuck wp, 13 M US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot) plus now waterproof. more

$200.00

FREE shipping

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Cole Haan Men's Kennedy Grand Chukka Waterproof Boot, Black wp, 9 M US

Cole Haan Men's Kennedy Grand Chukka Waterproof Boot, Black wp, 9 M US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot) plus now waterproof. more

$190.00

FREE shipping

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Cole Haan Men's 2.Zerogrand Stitchlite Chukka Water Resistant Boot, ch Habana Heathered/Brazilian Sand, 11.5 M US

Cole Haan Men's 2.Zerogrand Stitchlite Chukka Water Resistant Boot, ch Habana Heathered/Brazilian Sand, 11.5 M US

Forging a path in inclement weather just got a whole lot easier with Cole Haan next-generation 2.Zerøgrand chukka. The knit material is lightweight and water resistant to deal with rain, snow and sleet but easliy can be worn during the warm months as... more

$250.00

FREE shipping

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Cole Haan Men's Kennedy Grand Chukka Waterproof Boot, Woodbury wp, 7.5 M US

Cole Haan Men's Kennedy Grand Chukka Waterproof Boot, Woodbury wp, 7.5 M US

The kennedy collection represents the entire array of fashion dress shoes (chelsea, chukka, postman, single monk and wingtip boot) plus now waterproof. more

$190.00

FREE shipping

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Cole Haan Men's 2.Zerogrand Stitchlite Chukka Water Resistant Boot, Blueberry wr/Dove, 9 M US

Cole Haan Men's 2.Zerogrand Stitchlite Chukka Water Resistant Boot, Blueberry wr/Dove, 9 M US

Forging a path in inclement weather just got a whole lot easier with Cole Haan next-generation 2.Zerøgrand chukka. The knit material is lightweight and water resistant to deal with rain, snow and sleet but easliy can be worn during the warm months as... more

$250.00

FREE shipping

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Cole Haan Men's Pinch Rugged Chukka Fashion Boot, Tortoise Shell/After Dark, 13 M US

Cole Haan Men's Pinch Rugged Chukka Fashion Boot, Tortoise Shell/After Dark, 13 M US

A saw like rugged outsole that is very appealing to the eye when walking down the street. more

$180.00

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Cole Haan Men's Nantucket Rugged Plain Boot Fashion, British tan, 11 M US

Cole Haan Men's Nantucket Rugged Plain Boot Fashion, British tan, 11 M US

A rugged boot that has our iconic zerogrand outsole. more

$140.00

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Cole Haan Men's Pinch Rugged Chukka Fashion Boot, Tortoise Shell/After Dark, 11.5 M US

Cole Haan Men's Pinch Rugged Chukka Fashion Boot, Tortoise Shell/After Dark, 11.5 M US

A saw like rugged outsole that is very appealing to the eye when walking down the street. more

$180.00

FREE shipping

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