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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 Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Black Smooth
    Clarks Desert Boot(Men's) -Black/Black Leather
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -Burgundy Textile
    Clarks Desert Boot(Men's) -Natural Tan
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Olive Suede
    Clarks Desert Boot(Men's) -Tan Tumble
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $129.95 - $239.95
    Dr. Martens Baynes Chukka Boot
    New!
    Sale
    Dr. Martens Baynes Chukka Boot -Black Ajax Embossed/PU Coated Split Leather
    Dr. Martens Baynes Chukka Boot -Black Kaya
    Sale
    Dr. Martens Baynes Chukka Boot -Dark Grey Kaya Perfed
    Sale
    Dr. Martens Baynes Chukka Boot -Dark Red Kaya Perfed
    Sale
    Dr. Martens Baynes Chukka Boot -Grey Kaya
    Sale
    Dr. Martens Baynes Chukka Boot -Indigo Kaya Perfed
    Sale
    Dr. Martens Baynes Chukka Boot -Sand Kaya
    Sale
    Dr. Martens Baynes Chukka Boot -Mid Grey Ajax Embossed/PU Coated Split Leather
    Dr. Martens Baynes Chukka Boot -Mid Olive Ajax Embossed/PU Coated Split Leather
    Dr. Martens Baynes Chukka Boot -Old Oxblood Ajax Embossed/PU Coated Split Leather
    $82.95 - $109.95
    $110.00 - $115.00 up to 25% off
    TOMS Mateo Chukka Boot (Men's)
    New!
    Sale
    TOMS Mateo Chukka Boot(Men's) -Charcoal Herringbone Coated Canvas
    Sale
    TOMS Mateo Chukka Boot(Men's) -Chocolate Brown Slub Chambray
    Sale
    $82.95
    $98.00 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
    G.H. Bass & Co. Bennett Chukka (Men's)
    New!
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Black Tumbled Leather
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Brown Crazy Horse Leather
    Sale
    $99.99
    $135.00 26% off
    Robert Wayne Greyson Chukka Boot (Men's)
    New!
    Sale
    Robert Wayne Greyson Chukka Boot(Men's) -Taupe Suede
    Sale
    Robert Wayne Greyson Chukka Boot(Men's) -
    Sale
    Robert Wayne Greyson Chukka Boot(Men's) -Sand Suede
    Sale
    $59.00
    $79.00 25% off
    Nunn Bush Savage Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Savage Chukka Boot(Men's) -Cognac Leather
    Sale
    Nunn Bush Savage Chukka Boot(Men's) -Black Leather
    Sale
    Nunn Bush Savage Chukka Boot(Men's) -Brown Leather
    Sale
    $75.99
    $95.00 20% off
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    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) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
    Clarks Bushacre 2 Boot(Men's) -Chestnut Suede
    Clarks Bushacre 2 Boot(Men's) -Dark Brown
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Gold Suede
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Tobacco Suede
    Clarks Bushacre 2 Boot(Men's) -Walnut Suede
    $59.99 - $99.95
    $100.00 up to 40% 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) -Medium Brown Full Grain Leather/Mesh
    $89.95 - $124.95
    $125.00 up to 28% 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
    ECCO Jeremy Hybrid Chukka Boot (Men's)
    New!
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Black Cow Nubuck
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Cognac Cow Leather
    $157.50 - $209.95
    $210.00 up to 25% 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
    $109.95
    $110.00 - $140.00 up to 21% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee(Men's) -Black/Black Leather
    Clarks Wallabee(Men's) -Burgundy Suede
    Clarks Wallabee(Men's) -Dark Ochre Suede
    Clarks Wallabee(Men's) -Maple Suede
    Clarks Wallabee(Men's) -Red Suede
    $134.95 - $149.95
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Navy Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Suede
    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) -Black Waxy Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Cranberry Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Brown Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Tan Leather
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% 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
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(Men's) -Black Suede/Wool
    New
    UGG Freamon Chukka Boot(Men's) -Charcoal Suede/Wool
    New
    UGG Freamon Chukka Boot(Men's) -Navy Suede/Wool
    New
    UGG Freamon Chukka Boot(Men's) -New Navy Suede
    $109.95 - $119.95
    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
    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) -Dark Brown Suede
    Clarks Wallabee Boot(Men's) -Grey Suede
    Clarks Wallabee Boot(Men's) -Maple Suede
    Clarks Wallabee Boot(Men's) -Slate Blue Suede
    $139.95 - $159.95
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    New!
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Black Bear Track
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
    Sale
    $71.25
    $95.00 25% off