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    Discount Mens Chukka Boots

    1-36 of 82 results
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    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    $59.99 - $239.95
    $130.00 - $240.00 up to 54% 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
    $84.95 - $99.95
    $100.00 up to 15% 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
    $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
    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) -Chocolate Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $87.95
    $140.00 37% 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
    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
    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
    Sale
    $91.95 - $99.95
    $110.00 up to 16% 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
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Wheat Nubuck Leather
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Black Smooth Leather
    Sale
    $109.95 - $119.95
    $135.00 up to 19% off
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    $172.95 - $229.95
    $230.00 up to 25% off
    Nunn Bush Hawley Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Black Leather
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Brown Leather
    Sale
    $72.00
    $90.00 20% off
    Frye Mark Chukka (Men's)
    New!
    Sale
    Frye Mark Chukka(Men's) -Copper
    Sale
    Frye Mark Chukka(Men's) -Dark Brown
    Sale
    $223.95
    $298.00 25% off
    Nunn Bush Woodbury (Men's)
    New!
    Sale
    Nunn Bush Woodbury(Men's) -Brown Suede
    Sale
    Nunn Bush Woodbury(Men's) -Sand Suede
    Sale
    $64.00
    $80.00 20% off
    UGG Neumel Wheat Chukka Boot (Men's)
    New!
    Sale
    UGG Neumel Wheat Chukka Boot(Men's) -
    Sale
    $112.95
    $150.00 25% off
    Stacy Adams Astro 53404 (Men's)
    New!
    Sale
    Stacy Adams Astro 53404(Men's) -Black Smooth Leather
    Sale
    $79.95 - $89.95
    $90.00 up to 11% off
    Nunn Bush Rawson Chukka (Men's)
    New!
    Sale
    Nunn Bush Rawson Chukka(Men's) -Black Leather
    Sale
    Nunn Bush Rawson Chukka(Men's) -Chestnut Leather
    Sale
    $71.95
    $90.00 20% off
    Clarks Truxton Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Truxton Top Chukka Boot(Men's) -Black Waterproof Cow Full Grain Leather
    Sale
    $105.95
    $115.00 8% off
    UGG Bosley Chukka Boot (Men's)
    New!
    Sale
    UGG Bosley Chukka Boot(Men's) -Black
    Sale
    UGG Bosley Chukka Boot(Men's) -Chestnut
    Sale
    $142.95
    $190.00 25% off
    UGG Freamon Capra Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Capra Chukka Boot(Men's) -Chocolate
    Sale
    UGG Freamon Capra Chukka Boot(Men's) -Primer Leather
    Sale
    $97.95
    $130.00 25% 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
    $89.95 - $114.95
    $115.00 up to 22% off
    Rockport Path To Greatness High Chukka Boot (Men's)
    New!
    Sale
    Rockport Path To Greatness High Chukka Boot(Men's) -Grey Leather
    Sale
    Rockport Path To Greatness High Chukka Boot(Men's) -New Dress Blues Leather
    Sale
    Rockport Path To Greatness High Chukka Boot(Men's) -Tan Leather
    Sale
    $89.99
    $130.00 31% off
    Clarks Hawkley Rise Chukka (Men's)
    New!
    Sale
    Clarks Hawkley Rise Chukka(Men's) -Tan Leather
    Sale
    $114.95
    $125.00 8% off
    Boston Boot Co. Cambridge Chukka Boot (Men's)
    New!
    Sale
    Boston Boot Co. Cambridge Chukka Boot(Men's) -Brown Canvas
    Sale
    Boston Boot Co. Cambridge Chukka Boot(Men's) -Brown Leather
    Sale
    Boston Boot Co. Cambridge Chukka Boot(Men's) -Natural Canvas
    Sale
    $99.95 - $196.95
    $197.00 up to 49% off
    Nunn Bush Robinson Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Robinson Chukka Boot(Men's) -Black Leather
    Sale
    Nunn Bush Robinson Chukka Boot(Men's) -Chestnut Leather
    Sale
    $72.00
    $90.00 20% off
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(Men's) -Tan Waxee Leather
    Sale
    $99.95 - $109.95
    $110.00 up to 9% off
    UGG Hendrickson Chukka Boot (Men's)
    New!
    Sale
    UGG Hendrickson Chukka Boot(Men's) -Black Leather
    Sale
    UGG Hendrickson Chukka Boot(Men's) -Cordovan Leather
    Sale
    UGG Hendrickson Chukka Boot(Men's) -Navy Leather
    Sale
    UGG Hendrickson Chukka Boot(Men's) -Stout Suede
    Sale
    $97.95 - $129.95
    $130.00 - $140.00 up to 30% off
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy McGuffey Chukka Boot(Men's) -Chocolate Suede
    Sale
    $104.95 - $124.95
    $124.95 - $125.00 up to 16% off
    Dr. Martens Bonny 6 Eye Chukka Boot
    New!
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -Black 12oz Waxy Canvas/Kanga S
    Sale
    $59.95 - $84.95
    $80.00 - $85.00 up to 29% off
    Steve Madden Hendric Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Hendric Chukka Boot(Men's) -Green Suede/Leather
    Sale
    Steve Madden Hendric Chukka Boot(Men's) -Tan Suede/Leather
    Sale
    $67.95 - $89.95
    $90.00 up to 24% off
    Nunn Bush Tomah Ankle Boot (Men's)
    New!
    Sale
    Nunn Bush Tomah Ankle Boot(Men's) -Brown Suede
    Sale
    $64.00
    $80.00 20% off
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    New!
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Black Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Brown Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Chestnut Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Navy Suede
    Sale
    $86.45
    $100.00 14% off
    Florsheim Castellano Chukka (Men's)
    New!
    Sale
    Florsheim Castellano Chukka(Men's) -Black Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Brown Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Saddle Tan Leather
    Sale
    $119.95
    $140.00 14% off
    Dr. Scholl's Rhys Chukka Boot (Men's)
    New!
    Sale
    Dr. Scholl's Rhys Chukka Boot(Men's) -Black Leather
    Sale
    Dr. Scholl's Rhys Chukka Boot(Men's) -Brown Derby Leather
    Sale
    Dr. Scholl's Rhys Chukka Boot(Men's) -Taupe Suede
    Sale
    $74.95
    $94.99 21% 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
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    Andrew Marc Winchester Boot (Men's)
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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 ...
    Glide through a busy work day wearing the Ian Mid Chukka Boot by ECCO. This ankle boot has a direct-injected, ...
    ECCO Ian Mid Chukka Boot (Men's)
    Description:
    Glide through a busy work day wearing the Ian Mid Chukka Boot by ECCO. This ankle boot has a direct-injected, one-component welt-assisted polyurethane outsole. The leather lining ensures a soft and comfortable feel, and the removable leather-covered ECFS™ inlay sole ...