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    Discount Mens Chukka Boots

    1-36 of 88 results
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    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 Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    $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
    $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
    $119.95 - $149.95
    $150.00 up to 20% 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) -Black Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $71.95 - $89.95
    $90.00 up to 20% off
    Dunham Gavin-DUN Chukka (Men's)
    New!
    Sale
    Dunham Gavin-DUN Chukka(Men's) -Black Leather
    Sale
    Dunham Gavin-DUN Chukka(Men's) -Chocolate Leather
    Sale
    $116.25
    $160.00 27% 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
    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
    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
    $89.95 - $139.95
    $140.00 up to 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
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% 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
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Catalina Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    $91.95 - $134.95
    $135.00 up to 32% 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
    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 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
    Twisted X Boots MDM0017 Driving Mocs (Men's)
    New!
    Sale
    Twisted X Boots MDM0017 Driving Mocs(Men's) -Distressed Grain Leather
    Sale
    $69.95
    $109.99 36% off
    Rockport Dressports Business Chukka Boot (Men's)
    New!
    Sale
    Rockport Dressports Business Chukka Boot(Men's) -Black Leather
    Sale
    $108.95
    $135.00 19% 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
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% 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
    Clarks Stinson Lo (Men's)
    New!
    Sale
    Clarks Stinson Lo(Men's) -Beeswax Leather
    Sale
    Clarks Stinson Lo(Men's) -Black Leather
    Sale
    $89.95 - $94.95
    $100.00 up to 10% 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
    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
    Teva Durban Boot Leather (Men's)
    New!
    Sale
    Teva Durban Boot Leather(Men's) -Bison
    Sale
    Teva Durban Boot Leather(Men's) -Black
    Sale
    $97.95
    $130.00 25% off
    Boston Boot Co. Newbury Chukka Boot (Men's)
    New!
    Sale
    Boston Boot Co. Newbury Chukka Boot(Men's) -Black Leather
    Sale
    Boston Boot Co. Newbury Chukka Boot(Men's) -Natural Leather
    Sale
    $99.95
    $217.00 54% off
    Clarks Hawkley Rise Chukka (Men's)
    New!
    Sale
    Clarks Hawkley Rise Chukka(Men's) -Tan Leather
    Sale
    $63.95
    $125.00 49% 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
    $127.95
    $160.00 20% 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
    $71.95
    $90.00 20% 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
    Twisted X Boots MDMS003 (Men's)
    New!
    Sale
    Twisted X Boots MDMS003(Men's) -Dusty Tan Leather
    Sale
    $69.95
    $104.99 33% off
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    $204.95 - $229.95
    $230.00 up to 11% off
    Dunham REVseek (Men's)
    New!
    Sale
    Dunham REVseek(Men's) -Brown Leather
    Sale
    $112.50
    $155.00 27% 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
    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
    $119.95
    $140.00 14% off
    Florsheim Doon Chukka (Men's)
    New!
    Sale
    Florsheim Doon Chukka(Men's) -Black
    Sale
    Florsheim Doon Chukka(Men's) -Brown Smooth
    Sale
    $89.95
    $120.00 25% off