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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 233 results
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    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 Grizzly
    Dr. Martens Ember Desert Boot(Men's) -Dark Brown Grizzly
    Dr. Martens Ember Desert Boot(Men's) -Mid Grey Bronx Suede
    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
    Steve Madden Hendric Chukka Boot(Men's) -Green Suede/Leather
    Sale
    $74.95 - $89.95
    $90.00 up to 17% off
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black Leather
    New
    Steve Madden Harken Chukka Boot(Men's) -Grey Leather
    New
    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 - $89.95
    $90.00 up to 20% 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) -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) -Taupe Distressed Suede
    $69.95 - $239.95
    $130.00 - $240.00 up to 46% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -Chestnut
    UGG Neumel Boot(Men's) -China Tea
    UGG Neumel Boot(Men's) -New Navy Suede
    $129.95 - $139.95
    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) -British Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Light Grey Suede
    $59.99
    $100.00 40% off
    UGG Freamon Hyperweave Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Black Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Burnt Olive Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Seal Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Tango Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Marino Textile
    $119.95 - $149.95
    $150.00 up to 20% off
    Clarks Melshire Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Melshire Top Chukka Boot(Men's) -Black Cow Full Grain Leather
    Sale
    Clarks Melshire Top Chukka Boot(Men's) -Tan Cow Full Grain Leather
    Sale
    $69.95
    $110.00 36% 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) -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
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% 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) -Fudge Suede
    Clarks Wallabee(Men's) -Maple Suede
    Clarks Wallabee(Men's) -Navy Tumbled Leather
    Clarks Wallabee(Men's) -Ochre Suede
    Clarks Wallabee(Men's) -Tan Tumble
    Clarks Wallabee(Men's) -Taupe Synthetic
    $134.95 - $159.95
    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
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    New!
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Tan/Biscuit Grizzly
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Black Grizzly
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Dark Brown Grizzly
    $89.95 - $114.95
    $115.00 up to 22% off
    Boston Boot Co. Commonwealth Boot (Men's)
    New!
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Black Leather
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Brown/Nicotine Leather
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Natural/White Leather
    Sale
    $99.95
    $207.00 52% off
    Cole Haan GrandPro Chukka Sneaker (Men's)
    New!
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Oiled Velour Suede
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Brown Oiled Velour Suede
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Midnight Grey Oiled Velour Suede
    Sale
    $119.95
    $150.00 20% 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