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    Leather Chukka Boots

    1-36 of 205 results
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    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's) -Greystone Suede
    New
    Clarks Bushacre 2 Boot(Men's) -Sage Suede
    New
    Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Chestnut Suede
    $74.99 - $99.95
    $100.00 up to 25% off
    Timberland Killington Chukka Boot (Men's)
    New!
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Full Grain Leather/Mesh
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Leather
    Sale
    Timberland Killington Chukka Boot(Men's) -Black Full Grain Leather/Mesh
    Timberland Killington Chukka Boot(Men's) -Black Leather
    Timberland Killington Chukka Boot(Men's) -Light Brown Full Grain Leather
    Timberland Killington Chukka Boot(Men's) -Medium Brown Full Grain Leather/Mesh
    $74.95 - $124.95
    $125.00 up to 40% off
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Grey Suede
    Sale
    Clarks Wallabee Boot(Men's) -Slate Blue Suede
    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) -Dark Brown Suede
    Clarks Wallabee Boot(Men's) -Maple Suede
    $127.50 - $139.95
    $140.00 - $150.00 up to 15% off
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black  Leather
    Steve Madden Harken Chukka Boot(Men's) -Grey Leather
    $84.95 - $89.95
    $90.00 up to 6% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Black Smooth
    Sale
    Clarks Desert Boot(Men's) -Burgundy Textile
    Sale
    Clarks Desert Boot(Men's) -Midnight
    Sale
    Clarks Desert Boot(Men's) -Natural Tan
    Sale
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    Sale
    Clarks Desert Boot(Men's) -Olive Suede
    Sale
    Clarks Desert Boot(Men's) -Tan Tumble
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $100.95 - $204.00
    $130.00 - $240.00 up to 22% off
    Clarks Stratton Limit Boot (Men's)
    New!
    Sale
    Clarks Stratton Limit Boot(Men's) -Black Leather
    Sale
    Clarks Stratton Limit Boot(Men's) -Brown Leather
    Sale
    $119.95
    $135.00 11% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    New!
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Chocolate Leather
    $98.45 - $139.95
    $110.00 - $140.00 up to 10% off
    Cole Haan Williams Welt Chukka II (Men's)
    New!
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Chestnut Burnish Leather/Suede
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Driftwood/Driftwood Suede
    Sale
    $159.95
    $250.00 36% off
    UGG Freamon Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Brindle Full Grain Leather
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    UGG Freamon Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
    $79.95 - $149.95
    $150.00 up to 47% off
    UGG Maksim Chukka Boot (Men's)
    New!
    Sale
    UGG Maksim Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Maksim Chukka Boot(Men's) -Stormy Seas Suede
    Sale
    UGG Maksim Chukka Boot(Men's) -Black Suede
    UGG Maksim Chukka Boot(Men's) -Brindle Suede
    UGG Maksim Chukka Boot(Men's) -Grizzly Full Grain Leather
    UGG Maksim Chukka Boot(Men's) -Tamarind Suede
    $67.95 - $129.95
    $125.00 - $130.00 up to 46% off
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Castlerock Grey
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Boston Tan
    Rockport Rugged Bucks Waterproof Boot(Men's) -New Black Leather
    Rockport Rugged Bucks Waterproof Boot(Men's) -Tan Full Grain Leather
    $102.45 - $109.95
    $120.00 up to 15% off
    Clarks Un.Elott Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Un.Elott Mid Chukka Boot(Men's) -Black Cow Full Grain Leather
    Sale
    Clarks Un.Elott Mid Chukka Boot(Men's) -Burgundy Cow Full Grain Leather
    Sale
    $137.95
    $180.00 23% off
    Nunn Bush Lancaster Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
    Sale
    $56.00
    $80.00 30% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -Redwood
    New
    UGG Neumel Boot(Men's) -Black
    UGG Neumel Boot(Men's) -Chestnut
    UGG Neumel Boot(Men's) -China Tea
    UGG Neumel Boot(Men's) -Dark Fawn
    UGG Neumel Boot(Men's) -New Navy Suede
    $139.95 - $149.95
    Clarks Hinman Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Hinman Mid Chukka Boot(Men's) -Black Leather
    Sale
    Clarks Hinman Mid Chukka Boot(Men's) -Dark Tan Suede
    Sale
    $85.00
    $100.00 15% off
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Suede
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Catalina Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    $97.95 - $106.45
    $120.00 - $135.00 up to 27% off
    UGG Leighton Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Chestnut Suede
    $90.95 - $169.95
    $170.00 up to 46% off
    Clarks Clarkdale Bara Chukka Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Bara Chukka Boot(Men's) -Dark Tan Full Grain Leather
    Sale
    Clarks Clarkdale Bara Chukka Boot(Men's) -Olive Suede
    Sale
    $144.50
    $170.00 15% off
    Clarks Desert Trek (Men's)
    New!
    Sale
    Clarks Desert Trek(Men's) -Sand Suede
    Sale
    Clarks Desert Trek(Men's) -Black Interest Leather
    Clarks Desert Trek(Men's) -Black Suede
    Clarks Desert Trek(Men's) -Cola Hairy
    $119.00 - $139.95
    $140.00 up to 15% off
    UGG Dagmann Chukka Boot (Men's)
    New!
    Sale
    UGG Dagmann Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Dagmann Chukka Boot(Men's) -Navy Suede
    Sale
    UGG Dagmann Chukka Boot(Men's) -Olive Suede
    Sale
    UGG Dagmann Chukka Boot(Men's) -Chestnut Suede
    UGG Dagmann Chukka Boot(Men's) -Grizzly Full Grain Leather
    $99.95 - $199.95
    $200.00 up to 50% off