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    Mens Leather Chukka Boots

    1-36 of 146 results
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    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 Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Burgundy Textile
    New
    Clarks Desert Boot(Men's) -Natural Tan
    New
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Black Smooth
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -Khaki Leather
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    New
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Tan Tumble
    New
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $59.99 - $239.95
    $130.00 - $240.00 up to 54% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -New Navy Suede
    New
    UGG Neumel Boot(Men's) -Chestnut
    UGG Neumel Boot(Men's) -China Tea
    $129.95 - $139.95
    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) -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
    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) -Sand Suede
    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 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
    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
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Catalina Leather
    New
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Leather
    Rockport Classic Break Chukka Boot(Men's) -Black Suede
    Rockport Classic Break Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    $124.95 - $134.95
    $135.00 up to 7% 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
    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
    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
    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
    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
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% 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
    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
    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
    UGG Hendrickson Chukka Boot(Men's) -Black Suede
    UGG Hendrickson Chukka Boot(Men's) -Dark Fawn Suede
    $97.95 - $129.95
    $130.00 - $140.00 up to 30% 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
    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
    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
    Related Products
    The Neumel Donegal Chukka Boot features a soft sheepskin insole and leather and Donegal tweed upper. Cushioning foam insole lined ...
    UGG Neumel Donegal Chukka Boot (Men's)
    Description:
    The Neumel Donegal Chukka Boot features a soft sheepskin insole and leather and Donegal tweed upper. Cushioning foam insole lined with 17mm UGGpure™ wool that naturally wicks away moistureFlexible, lightweight molded EVA outsole with patented tread designWoolrich® Donegal tweed and ...
    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 ...
    Clean and simple design creates a classic silhouette; the Dorville Chukka Boot is perfect for any occasion with its wood-wrapped ...
    Crevo Dorville Chukka Boot (Men's)
    Description:
    Clean and simple design creates a classic silhouette; the Dorville Chukka Boot is perfect for any occasion with its wood-wrapped heel and flexible outsole. Genuine, supple leathers are stylish, while the memory foam sock adds comfort for all-day, easy wear. ...