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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.
Vionic Chase Chukka Boot (Men's)
New!
Sale
Vionic Chase Chukka Boot(Men's) -Tan Suede
Vionic Chase Chukka Boot(Men's) -Black Suede
$159.95
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 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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$59.95 - $65.95
$100.00 up to 40% off
Dunham Royalton Chukka (Men's)
New!
Sale
Dunham Royalton Chukka(Men's) -Brown Leather
Dunham Royalton Chukka(Men's) -Flagstone Leather
$149.95
Timberland Britton Hill Clean Chukka Boot (Men's)
New!
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Timberland Britton Hill Clean Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Britton Hill Clean Chukka Boot(Men's) -Medium Brown Full Grain Leather
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$104.95 - $129.99
$150.00 up to 30% off
UGG Neumel Boot (Men's)
New!
Sale
UGG Neumel Boot(Men's) -Charcoal Suede
New
UGG Neumel Boot(Men's) -Black
UGG Neumel Boot(Men's) -Chestnut
UGG Neumel Boot(Men's) -Chestnut Leather
UGG Neumel Boot(Men's) -Chestnut Two Tone Suede
UGG Neumel Boot(Men's) -Cordovan Cow Suede
UGG Neumel Boot(Men's) -Espresso Cow Suede
UGG Neumel Boot(Men's) -New Navy Suede
UGG Neumel Boot(Men's) -Salty Blue Suede
UGG Neumel Boot(Men's) -Taupe Suede
UGG Neumel Boot(Men's) -White Pepper Suede
$129.95 - $149.95
Timberland Classic TBL® Chukka (Men's)
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Timberland Classic TBL® Chukka(Men's) -Wheat Nubuck Leather
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Timberland Classic TBL® Chukka(Men's) -Black Smooth Leather
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$99.95
$135.00 26% off
Clarks Desert Boot (Men's)
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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) -Bordeaux Suede
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Clarks Desert Boot(Men's) -Brown/Brown 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) -Olive/Olive Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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Clarks Desert Boot(Men's) -Brown
$98.99 - $130.00
$130.00 - $140.00 up to 29% 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) -Black Suede
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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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Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
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$89.99
$100.00 - $110.00 up to 18% off
Cole Haan Original Grand Chukka Boot (Men's)
New!
Sale
Cole Haan Original Grand Chukka Boot(Men's) -Woodbury Leather/Ivory
New
Cole Haan Original Grand Chukka Boot(Men's) -Black Leather/Black
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Cole Haan Original Grand Chukka Boot(Men's) -Woodbury Leather/Dark Roast
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$149.99 - $179.95
$180.00 up to 17% off
ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
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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
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
New!
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Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
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$79.95
$114.99 30% off
Sorel Madson Chukka Waterproof Boot (Men's)
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Sorel Madson Chukka Waterproof Boot(Men's) -Black/Black Waterproof Full Grain Leather
New
Sorel Madson Chukka Waterproof Boot(Men's) -Camel Brown/Pebble Waterproof Suede
New
Sorel Madson Chukka Waterproof Boot(Men's) -Crouton Waterproof Full Grain Leather
New
Sorel Madson Chukka Waterproof Boot(Men's) -Major/Cordovan Waterproof Full Grain Leather
New
$170.00
Steve Madden Hestonn (Men's)
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Steve Madden Hestonn(Men's) -Tan Leather
Sale
$79.95
$90.00 11% off
Rockport Essential Details Waterproof Chukka Boot (Men's)
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Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
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$109.95
$125.00 12% off
Clarks Weaver Boot (Men's)
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Clarks Weaver Boot(Men's) -Tan/Tan Full Grain Leather
$160.00
Nunn Bush Galloway Chukka Boot (Men's)
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Nunn Bush Galloway Chukka Boot(Men's) -Beige Suede
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Nunn Bush Galloway Chukka Boot(Men's) -Dark Brown Suede
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$63.95
$80.00 20% off
Rockport Marshall Chukka Boot (Men's)
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Rockport Marshall Chukka Boot(Men's) -Cognac Leather
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Rockport Marshall Chukka Boot(Men's) -Black Leather
Rockport Marshall Chukka Boot(Men's) -Dark Brown Leather
$89.45 - $119.95
$120.00 up to 25% off
Steve Madden Harver Chukka Boot (Men's)
New!
Sale
Steve Madden Harver Chukka Boot(Men's) -Black Leather
New
Steve Madden Harver Chukka Boot(Men's) -Cognac Leather
Steve Madden Harver Chukka Boot(Men's) -Tan Leather
$89.95
Nunn Bush Lancaster Chukka Boot (Men's)
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Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
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$63.95
$80.00 20% off
Rockport Charson Lace Up Ankle Boot (Men's)
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Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
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Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
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$99.95
$140.00 29% off
Timberland Logan Bay Plain Toe Chukka Boot (Men's)
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Timberland Logan Bay Plain Toe Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Logan Bay Plain Toe Chukka Boot(Men's) -Medium Brown Full Grain Leather
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$99.95
$130.00 23% off
Clarks Stinson Lo (Men's)
New!
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Clarks Stinson Lo(Men's) -Beeswax Leather
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Clarks Stinson Lo(Men's) -Black Leather
Sale
$89.99
$100.00 10% off
UGG Dustin Chukka Boot (Men's)
New!
Sale
UGG Dustin Chukka Boot(Men's) -Black Suede
UGG Dustin Chukka Boot(Men's) -Chestnut Suede
UGG Dustin Chukka Boot(Men's) -Seal Suede
UGG Dustin Chukka Boot(Men's) -True Navy Suede
$99.95
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
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$84.98
$95.00 11% off