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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 261 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
    Sale
    UGG Freamon Chukka Boot(Men's) -Black Suede
    UGG Freamon Chukka Boot(Men's) -New Navy Suede
    $83.95 - $119.95
    $120.00 up to 30% off
    Dr. Martens Ember Desert Boot (Men's)
    New!
    Sale
    Dr. Martens Ember Desert Boot(Men's) -Dark Brown Bronx Suede
    Sale
    Dr. Martens Ember Desert Boot(Men's) -Black Slippery Waterproof Nubuck Leather
    New
    Dr. Martens Ember Desert Boot(Men's) -Tan Slippery Waterproof Nubuck Leather
    New
    Dr. Martens Ember Desert Boot(Men's) -Black Grizzly
    Dr. Martens Ember Desert Boot(Men's) -Dark Brown Grizzly
    Dr. Martens Ember Desert Boot(Men's) -Tan Grizzly
    $87.95 - $119.95
    $110.00 - $120.00 up to 20% off
    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
    TOMS Chukka Boot Leather (Men's)
    New!
    Sale
    TOMS Chukka Boot Leather(Men's) -Black Full Grain Leather
    Sale
    $96.95
    $129.00 25% off
    Steve Madden Hendric Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Hendric Chukka Boot(Men's) -Navy Suede/Leather
    Sale
    $62.95
    $90.00 30% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    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) -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) -Tan Tumble
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $69.95 - $239.95
    $130.00 - $240.00 up to 46% off
    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) -Brown Multi Leather/Fabric
    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
    $44.95 - $89.95
    $90.00 up to 50% off
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
    New
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    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) -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) -British Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Light Grey Suede
    $59.99 - $99.95
    $100.00 up to 40% off
    Clarks Chilver Hi Gore-Tex (Men's)
    New!
    Sale
    Clarks Chilver Hi Gore-Tex(Men's) -Black Leather
    Sale
    Clarks Chilver Hi Gore-Tex(Men's) -Dark Brown Nubuck
    Sale
    $149.95
    $160.00 6% off
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Grey Suede
    New
    Clarks Wallabee Boot(Men's) -Slate Blue Suede
    New
    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
    $139.95 - $149.95
    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
    $109.95
    $110.00 - $140.00 up to 21% off
    Frye Sam Chukka (Men's)
    New!
    Sale
    Frye Sam Chukka(Men's) -Chestnut Antique Leather
    Sale
    Frye Sam Chukka(Men's) -Cognac Antique Leather
    Sale
    $223.95 - $234.95
    $298.00 up to 25% off
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Waxy Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Brown 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) -Dark Tan Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Grey 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
    Naot Pilot (Men's)
    New!
    Sale
    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
    $199.95 - $239.95
    Ariat Spitfire Chukka Boot (Men's)
    New!
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber/Blue Laces Full Grain Leather
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Vintage Bomber Full Grain Leather
    Sale
    $89.95
    $99.95 10% off
    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
    $84.98
    $95.00 11% 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
    $63.99
    $80.00 20% 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