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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.
    1-36 of 255 results
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    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(Men's) -Chestnut/White
    UGG Freamon Chukka Boot(Men's) -Horchata Suede
    New
    UGG Freamon Chukka Boot(Men's) -Black Suede
    UGG Freamon Chukka Boot(Men's) -New Navy Suede
    $109.95 - $119.95
    Nunn Bush Hawley Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Brown Leather
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Black Leather
    Sale
    $71.95
    $90.00 20% off
    Steve Madden Hendric Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Hendric Chukka Boot(Men's) -Navy Suede/Leather
    Steve Madden Hendric Chukka Boot(Men's) -Green Suede/Leather
    Sale
    $74.95 - $89.95
    $90.00 up to 17% off
    Jambu Tavern Chukka Boot (Men's)
    New!
    Sale
    Jambu Tavern Chukka Boot(Men's) -Tobacco Nubuck/Vintage Leather
    New
    Jambu Tavern Chukka Boot(Men's) -Black/Grey Tumbled Nubuck/Vintage Leather
    New
    Jambu Tavern Chukka Boot(Men's) -Stone Nappa Leather/Tumbled Leather
    New
    $188.95
    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
    $99.95 - $139.95
    $140.00 up to 29% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Burgundy Textile
    New
    Clarks Desert Boot(Men's) -Natural Tan
    New
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Black Smooth
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -Khaki Leather
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    New
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Tan Tumble
    New
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $59.99 - $239.95
    $130.00 - $240.00 up to 54% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -New Navy Suede
    New
    UGG Neumel Boot(Men's) -Chestnut
    UGG Neumel Boot(Men's) -China Tea
    $129.95 - $139.95
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Charcoal Leather
    New
    Clarks Wallabee(Men's) -Fudge Suede
    New
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee(Men's) -Black/Black Leather
    Clarks Wallabee(Men's) -Maple Suede
    Clarks Wallabee(Men's) -Natural Tan
    New
    Clarks Wallabee(Men's) -Navy Tumbled Leather
    New
    Clarks Wallabee(Men's) -Tan Tumble
    New
    Clarks Wallabee(Men's) -Taupe Synthetic
    New
    $134.95 - $239.95
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black  Leather
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Brown Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $71.95 - $84.95
    $90.00 up to 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) -Sand Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -British Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Light Grey Suede
    $84.95 - $99.95
    $100.00 up to 15% 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
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -British Tan Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Khaki 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) -Brown Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Grey Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Loden Green
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% off
    Clarks Desert Trek (Men's)
    New!
    Sale
    Clarks Desert Trek(Men's) -Black Interest Leather
    New
    Clarks Desert Trek(Men's) -Cola Hairy
    New
    Clarks Desert Trek(Men's) -Black Suede
    Clarks Desert Trek(Men's) -Natural Tan
    New
    Clarks Desert Trek(Men's) -Sand Suede
    New
    $139.95 - $239.95
    Florsheim Castellano Chukka (Men's)
    New!
    Sale
    Florsheim Castellano Chukka(Men's) -Saddle Tan Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Black Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Brown Leather
    Sale
    $119.95
    $140.00 14% off
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    New!
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Dark Brown Full Grain Leather
    $99.95 - $109.95
    $110.00 up to 9% off
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Catalina Leather
    New
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Leather
    Rockport Classic Break Chukka Boot(Men's) -Black Suede
    Rockport Classic Break Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    $124.95 - $134.95
    $135.00 up to 7% off
    UGG Neumel Wheat Chukka Boot (Men's)
    New!
    Sale
    UGG Neumel Wheat Chukka Boot(Men's) -
    Sale
    $112.95
    $150.00 25% off
    Nunn Bush Galloway Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Galloway Chukka Boot(Men's) -Army Green Suede
    Sale
    Nunn Bush Galloway Chukka Boot(Men's) -Beige Suede
    Sale
    Nunn Bush Galloway Chukka Boot(Men's) -Dark Brown Suede
    Sale
    $63.99
    $80.00 20% off
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    The Florsheim Hamilton Chukka Boot is a classic dress boot with a modern edge, constructed from our finest materials. Clean ...
    Florsheim Hamilton Chukka Boot (Men's)
    Description:
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    The Leighton Bomber Chukka Boot features a two-tone suede upper and Twinsole™ removable insoles for the perfect blend of style ...
    UGG Leighton Bomber Chukka Boot (Men's)
    Description:
    The Leighton Bomber Chukka Boot features a two-tone suede upper and Twinsole™ removable insoles for the perfect blend of style and comfort. Twinsole™ interchangeable insoles: one set with 7mm curly UGGpure™ wool, one lined with leatherNatural crepe outsoleOiled suede combined ...