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    Leather Chukka Boots

    1-36 of 186 results
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    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Navy 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) -Tan Tumble
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $69.95 - $239.95
    $130.00 - $240.00 up to 46% 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) -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
    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) -Brown Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $53.95 - $89.95
    $90.00 up to 40% off
    Twisted X Boots MDMS003 (Men's)
    New!
    Sale
    Twisted X Boots MDMS003(Men's) -Dusty Tan Leather
    Sale
    $69.95
    $104.99 33% 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) -Dark Brown Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Chocolate Leather
    $109.95
    $110.00 - $140.00 up to 21% off
    Dr. Martens Ember Desert Boot (Men's)
    New!
    Sale
    Dr. Martens Ember Desert Boot(Men's) -Black Slippery Waterproof Nubuck Leather
    New
    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
    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
    Dr. Scholl's Hans Chukka Boot (Men's)
    New!
    Sale
    Dr. Scholl's Hans Chukka Boot(Men's) -Black Leather
    Sale
    $59.95
    $80.00 25% off
    Clarks Acre Bridge Chukka Boot (Women's)
    New!
    Sale
    Clarks Acre Bridge Chukka Boot(Women's) -Sand Cow Suede
    Sale
    Clarks Acre Bridge Chukka Boot(Women's) -Tan Cow Full Grain Leather
    Sale
    $59.95 - $76.95
    $95.00 up to 37% off
    Clarks Desert Boot (Women's)
    New!
    Sale
    Clarks Desert Boot(Women's) -Grey/Blue Suede
    Sale
    Clarks Desert Boot(Women's) -Light Cora Suede
    Sale
    Clarks Desert Boot(Women's) -Dark Navy Suede
    $57.95 - $119.95
    $120.00 - $140.00 up to 59% off
    Nunn Bush Galloway Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Galloway Plain Toe Chukka Boot(Men's) -Navy Suede
    Sale
    Nunn Bush Galloway Plain Toe Chukka Boot(Men's) -Tan Crazy Horse Leather
    Sale
    $63.99
    $80.00 20% off
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
    $204.95 - $229.95
    $230.00 up to 11% off
    UGG Hendrickson Capra Chukka Boot (Men's)
    New!
    Sale
    UGG Hendrickson Capra Chukka Boot(Men's) -Ceramic Leather
    Sale
    UGG Hendrickson Capra Chukka Boot(Men's) -Tamarind Leather
    Sale
    $87.95
    $160.00 45% off
    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
    $109.95
    $140.00 21% off
    Boston Boot Co. Cambridge Chukka Boot (Men's)
    New!
    Sale
    Boston Boot Co. Cambridge Chukka Boot(Men's) -Black Canvas
    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
    $197.00 49% off
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(Men's) -Tan Waxee Leather
    Sale
    Eastland Seneca(Men's) -Bomber Brown Leather
    Eastland Seneca(Men's) -Brown Leather 2
    Eastland Seneca(Men's) -Gray Leather
    Eastland Seneca(Men's) -Khaki Suede
    Eastland Seneca(Men's) -Natural Leather
    Eastland Seneca(Men's) -Peanut Leather
    $99.95 - $109.95
    $110.00 up to 9% off
    Rockport Ledge Hill Too Chukka Boot (Men's)
    New!
    Sale
    Rockport Ledge Hill Too Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    Sale
    Rockport Ledge Hill Too Chukka Boot(Men's) -Black Suede
    Rockport Ledge Hill Too Chukka Boot(Men's) -Dark Brown Leather
    $75.95 - $149.95
    $150.00 up to 49% 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
    Clarks Nevella Harper Chukka Boot (Women's)
    New!
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Black Leather
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Khaki Cow Suede
    Sale
    $63.95 - $95.95
    $160.00 up to 60% off
    UGG Leighton II Ankle Boot (Men's)
    New!
    Sale
    UGG Leighton II Ankle Boot(Men's) -British Tan Full Grain Leather
    Sale
    UGG Leighton II Ankle Boot(Men's) -Chestnut Full Grain Leather
    Sale
    $88.00 - $127.95
    $160.00 up to 45% off