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    Leather Chukka Boots

    1-36 of 154 results
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    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    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)-Black Smooth
    Clarks Desert Boot(Men's)-Brown
    Clarks Desert Boot(Men's)-Khaki Leather
    Clarks Desert Boot(Men's)-New Black Suede
    Clarks Desert Boot(Men's)-Oakwood Suede
    Clarks Desert Boot(Men's)-Off White Interest Suede
    Clarks Desert Boot(Men's)-Taupe Distressed Suede
    $59.99 - $159.95
    $130.00 - $160.00 up to 54% off
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's)-Beeswax 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
    $84.95
    $100.00 15% off
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's)-Black  Leather
    Steve Madden Harken Chukka Boot(Men's)-Black Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(Men's)-Brown Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(Men's)-Cognac Leather
    $89.95
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy Copeland Chukka Boot(Men's)-Black Tumbled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(Men's)-Camel Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Dark Gray Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Navy Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Red Brown Oiled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(Men's)-Tan Oiled Full Grain
    Johnston & Murphy Copeland Chukka Boot(Men's)-Taupe Water-Resistant Suede
    $149.95 - $154.95
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's)-Dark Green Suede
    Sale
    Clarks Wallabee Boot(Men's)-Beeswax/Beeswax Leather
    Clarks Wallabee Boot(Men's)-Dark Brown Suede
    Clarks Wallabee Boot(Men's)-Maple Suede
    $99.99 - $139.95
    $140.00 up to 29% off
    Clarks Stratton Limit Boot (Men's)
    Clarks Stratton Limit Boot (Men's)
    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)
    Rockport Charson Lace Up Ankle Boot (Men's)
    Rockport Charson Lace Up Ankle Boot (Men's)
    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
    $130.00 - $140.00 up to 23% off
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    New!
    Sale
    Clarks Desert Boot(Women's)-Beeswax Leather
    Clarks Desert Boot(Women's)-Black Suede
    Clarks Desert Boot(Women's)-Oakwood Suede
    Clarks Desert Boot(Women's)-Taupe Distressed
    $119.95
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    New!
    Sale
    Clarks Bushacre 2(Men's) -Black Leather
    Sale
    Clarks Bushacre 2(Men's) -Dark Green Suede
    Sale
    Clarks Bushacre 2(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2(Men's) -Navy Suede
    Sale
    $64.99 - $89.95
    $100.00 up to 35% off
    Pikolinos Glasgow 05M-6030F (Men's)
    Pikolinos Glasgow 05M-6030F (Men's)
    Pikolinos Glasgow 05M-6030F (Men's)
    New!
    Sale
    Pikolinos Glasgow 05M-6030F(Men's) -Choco/Cuero Leather
    Pikolinos Glasgow 05M-6030F(Men's) -Cuero
    $195.00 - $199.95
    UGG Bosley Chukka Boot (Men's)
    UGG Bosley Chukka Boot (Men's)
    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
    G.H. Bass & Co. Bennett Chukka (Men's)
    G.H. Bass & Co. Bennett Chukka (Men's)
    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
    $94.95
    $135.00 30% off
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Boston Tan
    Rockport Rugged Bucks Waterproof Boot(Men's) -Castlerock Grey
    Rockport Rugged Bucks Waterproof Boot(Men's) -Tan Full Grain Leather
    $109.95 - $119.95
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Mocha Oil Nubuck
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
    $172.95 - $229.95
    $230.00 up to 25% off
    Timberland Premium Chukka (Men's)
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    UGG Brompton Tweed (Men's)
    UGG Brompton Tweed (Men's)
    New!
    Sale
    UGG Brompton Tweed(Men's) -Grizzly
    Sale
    $149.95
    $200.00 25% off
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    New!
    Sale
    Florsheim Heritage Wingtip Boot(Men's) -Black Smooth/Milled
    Florsheim Heritage Wingtip Boot(Men's) -Cognac Smooth/Milled
    Florsheim Heritage Wingtip Boot(Men's) -Cognac Smooth/Navy
    $189.95
    Nunn Bush Hawley Chukka Boot (Men's)
    Nunn Bush Hawley Chukka Boot (Men's)
    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
    UGG Freamon Capra Chukka Boot (Men's)
    UGG Freamon Capra Chukka Boot (Men's)
    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
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    New!
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Aubergine Cow Suede
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Black Leather
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Khaki Cow Suede
    Sale
    $84.99 - $119.95
    $160.00 up to 47% off
    Clarks Truxton Top Chukka Boot (Men's)
    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
    Born Jax (Men's)
    Born Jax (Men's)
    New!
    Sale
    Born Jax(Men's) -Brown Full Grain Leather
    Sale
    $98.95
    $110.00 10% off
    UGG Leighton II Ankle Boot (Men's)
    UGG Leighton II Ankle Boot (Men's)
    UGG Leighton II Ankle Boot (Men's)
    UGG Leighton II Ankle Boot (Men's)
    New!
    Sale
    UGG Leighton II Ankle Boot(Men's) -Chestnut Full Grain Leather
    Sale
    UGG Leighton II Ankle Boot(Men's) -Stout Full Grain Leather
    Sale
    UGG Leighton II Ankle Boot(Men's) -British Tan Full Grain Leather
    $127.95 - $159.95
    $160.00 up to 20% off
    Related Products
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    Dr. Scholl's Original Collection Tyson Chukka Boot (Men's)
    Description:
    The Tyson is a burnished chukka boot built for durability. The distressed leather matches with a rubber sole and contrasted welt to provide a classic design that just works. The Energy Wave insole works to provide flexibility and breathability to ...
    Look your best in the Chad Boot, the classic dress appeal makes this a great option for casual and formal ...
    G.H. Bass & Co. Chad Boot (Men's)
    Description:
    Look your best in the Chad Boot, the classic dress appeal makes this a great option for casual and formal occasions. FeaturesGenuine leather sock liningLeather Welt and cushioned latex footbed.Stacked heel Shaft Height: 5.5" Circumference: 9.5" Fit: True to Size ...
    With a sport-inspired design, the versatile Woodson Chukka Boot from Dockers will play a key role in your wardrobe. Neoprene ...
    Dockers Woodson Chukka Boot (Men's)
    Description:
    With a sport-inspired design, the versatile Woodson Chukka Boot from Dockers will play a key role in your wardrobe. Neoprene sport liningMemory Foam insole shapes to foot for instant comfortFusion Footbed adds an extra layer of cushionFlyweight construction creates a ...