Phone
    Call
    1 (888) 200 - 8414
    Mon - Fri: 8:00 AM - Midnight ET
    Sat - Sun: 8:00 AM - 11:00 PM ET
    FREE shipping and FREE exchanges. every day. no minimum.
    0 Cart
    Loading...
    Your cart is currently unavailable
    Loading...
    Advanced search is currently unavailable

    Leather Chukka Boots

    1-36 of 166 results
     1 2 3 4 5 
    Sort by
    Display
    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
    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
    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
    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
    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
    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
    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
    $76.95
    $95.00 19% 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
    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
    Twisted X Boots MDMS003 (Men's)
    New!
    Sale
    Twisted X Boots MDMS003(Men's) -Dusty Tan Leather
    Sale
    $69.95
    $104.99 33% 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
    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
    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
    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
    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
    Sebago Vershire Chukka Boot (Men's)
    New!
    Sale
    Sebago Vershire Chukka Boot(Men's) -Black Waxy Oiled Full Grain Leather
    Sale
    Sebago Vershire Chukka Boot(Men's) -Brown Waxy Oiled Full Grain Leather
    Sebago Vershire Chukka Boot(Men's) -Dark Taupe Waxy Oiled Full Grain Leather
    $107.95 - $139.95
    $140.00 up to 23% off
    Related Products
    A classic meets comfort with Crevo's Cray Chukka Boot. Soft mixed materials create a simple, yet unique look, while the ...
    Crevo Cray Chukka Boot (Men's)
    Description:
    A classic meets comfort with Crevo's Cray Chukka Boot. Soft mixed materials create a simple, yet unique look, while the real leather welt calls back to the style's roots. Combined with a flexible, non-slip rubber outsole and memory foam footbed, ...
    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. ...
    Dustin is a lace up waterproof boot that provides comfort and support. Lightweight EVA midosle and memory foam cushioning provide ...
    Aetrex Ventures Collection Dustin Chukka Boot (Men's)
    Description:
    Dustin is a lace up waterproof boot that provides comfort and support. Lightweight EVA midosle and memory foam cushioning provide a customized fit and comfort. Lynco® orthotics and Aegis® annti-microbial technology provide support and protects against fungi, odor and bacteria. ...