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Mens Chukka Boots

Men's chukka boots are made with the fashionable gentleman in mind. They are open-laced ankle boots with rubber or leather soles, and you can find great pairs at the best price right here. We have chukka boots for men from all the top brands, like Timberland, UGG, Dr. Martens, ECCO, Clarks and Johnston & Murphy, so you know you'll find the right pair.
Eastland Jack Chukka Boot (Men's)
New!
Sale
Eastland Jack Chukka Boot(Men's) -Burgundy Full Grain Leather
New
Eastland Jack Chukka Boot(Men's) -Brown Leather
Eastland Jack Chukka Boot(Men's) -Grey Full Grain Leather
Eastland Jack Chukka Boot(Men's) -Peanut Leather
$124.95
Florsheim Edge Chukka Boot (Men's)
New!
Sale
Florsheim Edge Chukka Boot(Men's) -Black Nubuck
Florsheim Edge Chukka Boot(Men's) -Charcoal Nubuck
Florsheim Edge Chukka Boot(Men's) -Loden Nubuck
Florsheim Edge Chukka Boot(Men's) -Navy Nubuck
Florsheim Edge Chukka Boot(Men's) -Olive Nubuck
$109.95
UGG Cali Chukka Sneaker (Men's)
New!
Sale
UGG Cali Chukka Sneaker(Men's) -Chestnut Suede
UGG Cali Chukka Sneaker(Men's) -Navy Full Grain Leather
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UGG Cali Chukka Sneaker(Men's) -Stout Full Grain Leather
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UGG Cali Chukka Sneaker(Men's) -Antelope Suede
UGG Cali Chukka Sneaker(Men's) -Navy Suede
UGG Cali Chukka Sneaker(Men's) -Seal Suede
$114.95 - $179.95
$180.00 - $200.00 up to 43% off
Clarks Wallabee Boot (Men's)
New!
Sale
Clarks Wallabee Boot(Men's) -Beeswax/Beeswax Leather
Clarks Wallabee Boot(Men's) -Black/Black Leather
Clarks Wallabee Boot(Men's) -Black/Black Suede
Clarks Wallabee Boot(Men's) -Maple Suede
$149.95
Clarks Bushacre 2 Boot (Men's)
New!
Sale
Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
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Clarks Bushacre 2 Boot(Men's) -Black Leather
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Clarks Bushacre 2 Boot(Men's) -Black Suede
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Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Olive Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
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Clarks Bushacre 2 Boot(Men's) -Grey Leather
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Clarks Bushacre 2 Boot(Men's) -Navy Leather
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Clarks Bushacre 2 Boot(Men's) -Wheat Suede
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Clarks Bushacre 2 Boot(Men's) -Wine Leather
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$54.99 - $67.99
$100.00 up to 45% off
ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
New!
Sale
ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Black Cow Oil Nubuck
ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Mocha Cow Oil Nubuck
$169.95 - $229.95
Ariat Spitfire Chukka Boot (Men's)
New!
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Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
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Ariat Spitfire Chukka Boot(Men's) -Aged Mahogany Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber/Blue Laces Full Grain Leather
Ariat Spitfire Chukka Boot(Men's) -Vintage Bomber Full Grain Leather
$99.95 - $109.95
$99.95 - $109.95 up to 9% off
Clarks Stinson Hi Moc Toe Boot (Men's)
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Clarks Stinson Hi Moc Toe Boot(Men's) -Beeswax Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Black Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Olive Leather
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$89.99 - $98.99
$100.00 - $110.00 up to 10% off
Steve Madden Harken Chukka Boot (Men's)
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Steve Madden Harken Chukka Boot(Men's) -Black  Leather
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Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
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$79.95
$90.00 11% off
Timberland Davis Square Fabric/Leather Chukka Boot (Men's)
New!
Sale
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Medium Grey Nubuck/Cordura® Fiber
New
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Navy Nubuck/Cordura® Fiber
New
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Black Nubuck/Cordura® EcoMade Fiber
Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Wheat Nubuck/Cordura® EcoMade Fiber
$59.95 - $79.95
Dunham Royalton Chukka (Men's)
New!
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Dunham Royalton Chukka(Men's) -Flagstone Leather
New
Dunham Royalton Chukka(Men's) -Brown Leather
$149.95
Rockport Marshall Chukka Boot (Men's)
New!
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Rockport Marshall Chukka Boot(Men's) -Black Leather
Rockport Marshall Chukka Boot(Men's) -Cognac Leather
Rockport Marshall Chukka Boot(Men's) -Dark Brown Leather
$89.45 - $119.95
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
New!
Sale
Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
Sale
$99.95
$114.99 13% off
Rockport Essential Details Waterproof Chukka Boot (Men's)
New!
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Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
Sale
$109.95
$125.00 12% off
Dunham Johnson Chukka (Men's)
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Dunham Johnson Chukka(Men's) -Black Leather
$149.95
Steve Madden Hestonn (Men's)
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Steve Madden Hestonn(Men's) -Tan Leather
Sale
$79.95
$90.00 11% off
Clarks Desert Boot (Men's)
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Clarks Desert Boot(Men's) -Bordeaux Suede
New
Clarks Desert Boot(Men's) -Brown/Brown Suede
New
Clarks Desert Boot(Men's) -Beeswax Full Grain Leather
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Clarks Desert Boot(Men's) -Black/Black Suede
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Clarks Desert Boot(Men's) -Blue/Grey Suede
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Clarks Desert Boot(Men's) -Mahogany Suede
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Clarks Desert Boot(Men's) -Navy Canvas
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Clarks Desert Boot(Men's) -Oak Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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Clarks Desert Boot(Men's) -Beeswax
Clarks Desert Boot(Men's) -Brown
Clarks Desert Boot(Men's) -Olive/Olive Suede
New
$96.99 - $129.95
$130.00 - $140.00 up to 31% off
Clarks Hinman Mid Chukka Boot (Men's)
New!
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Clarks Hinman Mid Chukka Boot(Men's) -Black Leather
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Clarks Hinman Mid Chukka Boot(Men's) -Dark Tan Suede
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Clarks Hinman Mid Chukka Boot(Men's) -Mahogany Leather
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$89.99
$100.00 10% off
Rockport Dustyn Chukka Boot (Men's)
New!
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Rockport Dustyn Chukka Boot(Men's) -Black Leather
New
Rockport Dustyn Chukka Boot(Men's) -New Caramel Leather
New
$124.95
Dr. Martens Work Sussex 3 Eye Chukka (Men's)
New!
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Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Black Bear Track
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Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
Sale
$84.98
$95.00 11% off
Timberland Killington Chukka Boot (Men's)
New!
Sale
Timberland Killington Chukka Boot(Men's) -Black Leather
Sale
$99.95
$125.00 20% off