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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.
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    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
    Dockers Tulane Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Dark Tan Burnished Crazyhorse
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Black Oily Tumbled Full Grain
    Sale
    Dockers Tulane Plain Toe Chukka Boot(Men's) -Chocolate Oily Tumbled Full Grain
    Sale
    $69.99
    $90.00 22% off
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    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 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
    Clarks Clarkdale Jean Chukka Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Jean Chukka Boot(Men's) -Dark Tan Full Grain Leather
    Sale
    Clarks Clarkdale Jean Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    $144.50
    $170.00 15% off
    ECCO Jeremy Hybrid Chukka Boot (Men's)
    New!
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Cognac Cow Leather
    Sale
    $140.00
    $210.00 33% off
    TOMS Mateo Chukka Boot (Men's)
    New!
    Sale
    TOMS Mateo Chukka Boot(Men's) -Chocolate Brown Slub Chambray
    Sale
    TOMS Mateo Chukka Boot(Men's) -Charcoal Herringbone Coated Canvas
    Sale
    $78.40 - $82.95
    $98.00 up to 20% 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!
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    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 Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Suede
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Waxy Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Cranberry Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Beeswax Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Loden Green
    $80.95 - $109.95
    $100.00 - $110.00 up to 26% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Burgundy Suede
    Sale
    Clarks Wallabee(Men's) -Dark Ochre Suede
    Sale
    Clarks Wallabee(Men's) -Maple Suede
    Sale
    Clarks Wallabee(Men's) -Red Suede
    Sale
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee(Men's) -Black/Black Leather
    $114.75 - $134.95
    $135.00 - $160.00 up to 27% 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
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(Men's) -Redwood
    New
    UGG Freamon Chukka Boot(Men's) -Black Suede/Wool
    Sale
    UGG Freamon Chukka Boot(Men's) -Charcoal Suede/Wool
    Sale
    UGG Freamon Chukka Boot(Men's) -Navy Suede/Wool
    Sale
    UGG Freamon Chukka Boot(Men's) -New Navy Suede
    $59.95 - $149.95
    $110.00 - $150.00 up to 45% 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