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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!
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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) -Grey Leather
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Clarks Bushacre 2 Boot(Men's) -Navy Leather
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Clarks Bushacre 2 Boot(Men's) -Taupe Distressed Suede
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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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Clarks Bushacre 2 Boot(Men's) -Brown Suede
$58.95 - $99.95
$100.00 up to 41% off
UGG Neumel Boot (Men's)
New!
Sale
UGG Neumel Boot(Men's) -Taupe Suede
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UGG Neumel Boot(Men's) -Black
UGG Neumel Boot(Men's) -Charcoal Suede
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) -White Pepper Suede
$107.95 - $149.95
$130.00 - $150.00 up to 23% 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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$120.00 - $130.00
$140.00 up to 14% off
Clarks Stinson Hi Moc Toe Boot (Men's)
New!
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Clarks Stinson Hi Moc Toe Boot(Men's) -Taupe Distressed Suede
New
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 - $109.95
$100.00 - $110.00 up to 18% off
Clarks Desert Boot (Men's)
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Clarks Desert Boot(Men's) -Sand/Sand Suede
New
Clarks Desert Boot(Men's) -Bordeaux 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) -Olive/Olive Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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Clarks Desert Boot(Men's) -Beeswax Full Grain Leather
Clarks Desert Boot(Men's) -Black/Black Suede
Clarks Desert Boot(Men's) -Brown
Clarks Desert Boot(Men's) -Brown/Brown Suede
Clarks Desert Boot(Men's) -Oak Suede
$93.95 - $129.95
$130.00 - $140.00 up to 33% off
Steve Madden Hestonn (Men's)
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Steve Madden Hestonn(Men's) -Tan Leather
Sale
$79.95
$90.00 11% off
UGG Neumel Waterproof Chukka Boot (Men's)
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UGG Neumel Waterproof Chukka Boot(Men's) -True Navy Full Grain Leather
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UGG Neumel Waterproof Chukka Boot(Men's) -Black Full Grain Leather
UGG Neumel Waterproof Chukka Boot(Men's) -Charcoal Full Grain Leather
UGG Neumel Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
$114.95 - $179.95
$180.00 up to 36% off
Rockport Sharp & Ready Chukka Boot (Men's)
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Rockport Sharp & Ready Chukka Boot(Men's) -Black Leather
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Rockport Sharp & Ready Chukka Boot(Men's) -Saddle Brown Leather
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Rockport Sharp & Ready Chukka Boot(Men's) -Brown/Brown Leather
Rockport Sharp & Ready Chukka Boot(Men's) -Castlerock Grey Leather
Rockport Sharp & Ready Chukka Boot(Men's) -Tobacco Suede
$116.99 - $155.00
$139.95 - $140.00 up to 16% off
ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
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ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Mocha Cow Oil Nubuck
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ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Black Cow Oil Nubuck
ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Cocoa Brown Cow Oil Nubuck
$129.95 - $229.95
$170.00 - $230.00 up to 24% off
Dunham Johnson Chukka (Men's)
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Dunham Johnson Chukka(Men's) -Black Leather
Sale
$111.95
$150.00 25% off
Rockport Rugged Bucks Waterproof Boot (Men's)
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Rockport Rugged Bucks Waterproof Boot(Men's) -Boston Tan
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Rockport Rugged Bucks Waterproof Boot(Men's) -Tan Full Grain Leather
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$100.00
$120.00 17% off
Dr. Martens Work Sussex 3 Eye Chukka (Men's)
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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
UGG Dustin Chukka Boot (Men's)
New!
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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
Timberland Kendrick Chukka Boot (Men's)
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Timberland Kendrick Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Kendrick Chukka Boot(Men's) -Medium Brown Full Grain Leather
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$94.95
$140.00 32% off
UGG Neumel Unlined Leather Chukka Boot (Men's)
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UGG Neumel Unlined Leather Chukka Boot(Men's) -Burgundy Suede
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UGG Neumel Unlined Leather Chukka Boot(Men's) -Moss Green Suede
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UGG Neumel Unlined Leather Chukka Boot(Men's) -Charcoal Unlined Leather
UGG Neumel Unlined Leather Chukka Boot(Men's) -Chestnut Unlined Leather
UGG Neumel Unlined Leather Chukka Boot(Men's) -Pumice Unlined Leather
$74.95 - $124.95
$100.00 - $125.00 up to 25% off
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
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Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
Sale
$99.95
$114.99 13% off
Naot Pilot (Men's)
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Naot Pilot(Men's) -Brown Gradient Handcrafted Leather
Naot Pilot(Men's) -Desert Suede
Naot Pilot(Men's) -Gray Suede
Naot Pilot(Men's) -Oily Coal Nubuck
Naot Pilot(Men's) -Seal Brown Suede
Naot Pilot(Men's) -Vintage Grey Leather
$239.95
Clarks Desert Trek (Men's)
New!
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Clarks Desert Trek(Men's) -Nut Brown Suede/Full Grain Leather
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Clarks Desert Trek(Men's) -Black/Black/Black Suede
$125.95 - $139.95
$140.00 up to 10% off
Twisted X Boots MDM0061 Driving Mocs Chukka Boot (Men's)
New!
Sale
Twisted X Boots MDM0061 Driving Mocs Chukka Boot(Men's) -Tan/Tooled Flowers Leather
Sale
$129.95
$139.99 7% off
Twisted X Boots MDM0014 (Men's)
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Twisted X Boots MDM0014(Men's) -Copper Leather
$104.99
Ariat Spitfire Chukka Boot (Men's)
New!
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Ariat Spitfire Chukka Boot(Men's) -Distressed Brown/Camo Full Grain Leather
New
Ariat Spitfire Chukka Boot(Men's) -Latigo Brown/Cortez Aztec Full Grain/Fabric
New
Ariat Spitfire Chukka Boot(Men's) -Aged Mahogany Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain 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) -Wicker/Mustard Navajo Full Grain Leather/Fabric
New
$99.95 - $109.95
Steve Madden Harken Chukka Boot (Men's)
New!
Sale
Steve Madden Harken Chukka Boot(Men's) -Black  Leather
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Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
Sale
$44.95 - $79.95
$90.00 up to 50% off
TOMS Chukka Boot Leather (Men's)
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TOMS Chukka Boot Leather(Men's) -Black Melange Woven
TOMS Chukka Boot Leather(Men's) -Brown Waterproof Pull Up Leather
$97.95 - $139.00
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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$72.00
$80.00 10% 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 Bardstown Plain Toe Chukka Boot (Men's)
New!
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Timberland Bardstown Plain Toe Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Bardstown Plain Toe Chukka Boot(Men's) -Medium Brown Full Grain Leather
Sale
$179.95
$300.00 40% off