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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 251 results
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    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
    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) -Fudge Suede
    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
    $90.95 - $239.95
    $130.00 - $240.00 up to 30% 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
    $71.95 - $84.95
    $90.00 up to 20% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -Black
    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
    $84.95 - $99.95
    $100.00 up to 15% 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) -Charcoal Leather
    Clarks Wallabee(Men's) -Fudge Suede
    Clarks Wallabee(Men's) -Maple Suede
    Clarks Wallabee(Men's) -Navy Tumbled Leather
    Clarks Wallabee(Men's) -Night Blue
    Clarks Wallabee(Men's) -Tan Tumble
    Clarks Wallabee(Men's) -Taupe Synthetic
    $134.95 - $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
    $99.95 - $139.95
    $140.00 up to 29% 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
    Clarks Stinson Hi Moc Toe Boot(Men's) -Khaki Leather
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% 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
    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
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Wheat Nubuck Leather
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    Timberland Classic TBLŪ Chukka(Men's) -Black Smooth Leather
    Sale
    $109.95 - $119.95
    $135.00 up to 19% off
    Clarks Hawkley Rise Chukka (Men's)
    New!
    Sale
    Clarks Hawkley Rise Chukka(Men's) -Tan Leather
    Sale
    $87.95
    $125.00 30% off
    Drew Keith (Men's)
    New!
    Sale
    Drew Keith(Men's) -Black Leather
    Sale
    Drew Keith(Men's) -Brandy Leather
    Sale
    $166.45
    $190.00 12% off
    Florsheim Rockit Chukka (Men's)
    New!
    Sale
    Florsheim Rockit Chukka(Men's) -Brown Distressed Milled Leather
    Sale
    Florsheim Rockit Chukka(Men's) -Black Distressed Milled Leather
    $101.95 - $134.95
    $135.00 up to 24% 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
    Related Products
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    Dr. Scholl's Original Collection Tyson Chukka Boot (Men's)
    Description:
    The Tyson is a burnished chukka boot built for durability. The distressed leather matches with a rubber sole and contrasted welt to provide a classic design that just works. The Energy Wave insole works to provide flexibility and breathability to ...
    Put the final stylish touch on your look with the refreshing Vershire Chukka Boot. Showing off a handsewn genuine moccasin ...
    Sebago Vershire Chukka Boot (Men's)
    Description:
    Put the final stylish touch on your look with the refreshing Vershire Chukka Boot. Showing off a handsewn genuine moccasin construction that provides custom comfort and extended durability. Lace up closureNickel free non-corrosive eyeletsLeather rawhide lacesOrthoLite® cushioned footbedGenuine leather welt ...
    The Bosley Chukka Boot features a rugged bomber-jacket-inspired full grain leather upper and soft, moisture-wicking UGGpure™ wool insole. 10mm UGGpure™ ...
    UGG Bosley Chukka Boot (Men's)
    Description:
    The Bosley Chukka Boot features a rugged bomber-jacket-inspired full grain leather upper and soft, moisture-wicking UGGpure™ wool insole. 10mm UGGpure™ wool insole naturally wicks away moistureTreadlite by UGG™ outsoleBomber-jacket-inspired full-grain leather upper2-eyelet designLeather lace10mm ...