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    Leather Chukka Boots

    1-36 of 179 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)
    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)
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(
Men's) -
Bronze Nubuck
    New
    Clarks Desert Boot(
Men's) -
Camel Leather
    New
    Clarks Desert Boot(
Men's) -
Amber Gold
    Clarks Desert Boot(
Men's) -
Beeswax
    Clarks Desert Boot(
Men's) -
Black Smooth
    Clarks Desert Boot(
Men's) -
Brown
    Clarks Desert Boot(
Men's) -
Charcoal Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Green Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Tan Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Taupe Nubuck
    New
    Clarks Desert Boot(
Men's) -
Khaki Leather
    New
    Clarks Desert Boot(
Men's) -
Multicolour Suede
    New
    Clarks Desert Boot(
Men's) -
Navy Leather
    Clarks Desert Boot(
Men's) -
New Black Suede
    Clarks Desert Boot(
Men's) -
Nut Brown Suede
    New
    Clarks Desert Boot(
Men's) -
Off White Interest Suede
    Clarks Desert Boot(
Men's) -
Petrol Blue Leather
    New
    Clarks Desert Boot(
Men's) -
Rust Leather
    Clarks Desert Boot(
Men's) -
Taupe Distressed Suede
    Clarks Desert Boot(
Men's) -
Wolf Suede
    New
    $129.95 - $179.95
    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) -
Sand Suede
    Sale
    $84.95
    $99.00 14% off
    UGG Freamon II Chukka Boot (Men's)
    UGG Freamon II Chukka Boot (Men's)
    UGG Freamon II Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon II Chukka Boot(
Men's) -
Black Full Grain Leather
    New
    UGG Freamon II Chukka Boot(
Men's) -
Espresso Full Grain Leather
    New
    $149.95
    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)
    Clarks Desert Boot (Women's)
    New!
    Sale
    Clarks Desert Boot(
Women's) -
Black/White Graphic Print Suede
    New
    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 - $139.95
    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)
    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)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(
Men's) -
Bronze Suede
    New
    Clarks Wallabee Boot(
Men's) -
Multicolour Suede
    New
    Clarks Wallabee Boot(
Men's) -
Beeswax/Beeswax Leather
    Clarks Wallabee Boot(
Men's) -
Black/Black Leather
    Clarks Wallabee Boot(
Men's) -
Black/Black Suede
    Clarks Wallabee Boot(
Men's) -
Dark Brown Suede
    Clarks Wallabee Boot(
Men's) -
Dark Green Suede
    Clarks Wallabee Boot(
Men's) -
Maple Suede
    Clarks Wallabee Boot(
Men's) -
Navy Leather
    Clarks Wallabee Boot(
Men's) -
Petrol Blue Leather
    New
    Clarks Wallabee Boot(
Men's) -
Rust Vintage Suede
    New
    $139.95 - $199.95
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    New!
    Sale
    Timberland Grantly Chukka Boot(
Men's) -
Black Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Brown Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Dark Brown Full Grain Leather/Suede
    $139.95
    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
    New
    Clarks Nevella Harper Chukka Boot(
Women's) -
Black Leather
    New
    Clarks Nevella Harper Chukka Boot(
Women's) -
Khaki Cow Suede
    New
    $159.95
    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
    Pikolinos Glasgow 05M-6030F (Men's)
    Pikolinos Glasgow 05M-6030F (Men's)
    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
    New
    Pikolinos Glasgow 05M-6030F(
Men's) -
Black
    Pikolinos Glasgow 05M-6030F(
Men's) -
Cuero
    Pikolinos Glasgow 05M-6030F(
Men's) -
Ron/Grey
    $195.00 - $199.95
    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
    Rockport Charson Lace Up Ankle Boot(
Men's) -
Chocolate Leather
    Rockport Charson Lace Up Ankle Boot(
Men's) -
Dark Brown Leather
    Sale
    $109.95 - $139.95
    $140.00 up to 21% 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)
    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
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Castlerock Grey
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Tan Full Grain Leather
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Espresso Nubuck
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
New Dress Blues Leather
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Wheat Nubuck
    $109.95 - $119.95
    $120.00 up to 8% 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) -
British Tan Full Grain Leather
    New
    UGG Leighton II Ankle Boot(
Men's) -
Chestnut Full Grain Leather
    New
    UGG Leighton II Ankle Boot(
Men's) -
Stout Full Grain Leather
    New
    $159.95
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(
Men's) -
Bomber Brown Leather
    Eastland Seneca(
Men's) -
Brown Leather 2
    Eastland Seneca(
Men's) -
Tan Waxee Leather
    Sale
    Eastland Seneca(
Men's) -
Gray Leather
    Eastland Seneca(
Men's) -
Khaki Suede
    Eastland Seneca(
Men's) -
Natural Leather
    Eastland Seneca(
Men's) -
Navy Leather
    Eastland Seneca(
Men's) -
Peanut Leather
    $99.95 - $109.95
    $110.00 up to 9% 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)
    New!
    Sale
    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
    Sale
    $84.95 - $89.95
    $90.00 up to 6% off
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Hendric Chukka Boot(
Men's) -
Green Suede/Leather
    New
    Steve Madden Hendric Chukka Boot(
Men's) -
Navy Suede/Leather
    New
    Steve Madden Hendric Chukka Boot(
Men's) -
Tan Suede/Leather
    New
    $89.95
    Clarks Un.Astin Chukka Boot (Women's)
    Clarks Un.Astin Chukka Boot (Women's)
    Clarks Un.Astin Chukka Boot (Women's)
    Clarks Un.Astin Chukka Boot (Women's)
    Clarks Un.Astin Chukka Boot (Women's)
    New!
    Sale
    Clarks Un.Astin Chukka Boot(
Women's) -
Aubergine Cow Suede
    New
    Clarks Un.Astin Chukka Boot(
Women's) -
Black Cow Full Grain Leather
    New
    Clarks Un.Astin Chukka Boot(
Women's) -
Khaki Cow Full Grain Leather
    New
    Clarks Un.Astin Chukka Boot(
Women's) -
Navy Cow Suede
    New
    $149.95
    Clarks Athie Terra Wedge Bootie (Women's)
    Clarks Athie Terra Wedge Bootie (Women's)
    Clarks Athie Terra Wedge Bootie (Women's)
    Clarks Athie Terra Wedge Bootie (Women's)
    New!
    Sale
    Clarks Athie Terra Wedge Bootie(
Women's) -
Black Leather
    New
    Clarks Athie Terra Wedge Bootie(
Women's) -
Dark Taupe Suede
    New
    Clarks Athie Terra Wedge Bootie(
Women's) -
Rust Vintage Suede
    New
    $149.95
    Born Jax (Men's)
    Born Jax (Men's)
    Born Jax (Men's)
    New!
    Sale
    Born Jax(
Men's) -
Brown Full Grain Leather
    Born Jax(
Men's) -
Tan Full Grain Leather
    $108.95 - $109.95
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    New!
    Sale
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Dark Bitter Chocolate 2 Suede
    New
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Black
    Rockport Total Motion Fusion Desert Boot(
Men's) -
New Dress Blues
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Rocksand
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Tan
    $149.95
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    New!
    Sale
    Florsheim Castellano Chukka(
Men's) -
Black Leather
    Florsheim Castellano Chukka(
Men's) -
Brown Leather
    Florsheim Castellano Chukka(
Men's) -
Saddle Tan Leather
    $139.95
    Merrell Around Town Chukka Boot (Women's)
    Merrell Around Town Chukka Boot (Women's)
    Merrell Around Town Chukka Boot (Women's)
    Merrell Around Town Chukka Boot (Women's)
    Merrell Around Town Chukka Boot (Women's)
    New!
    Sale
    Merrell Around Town Chukka Boot(
Women's) -
Granite
    New
    Merrell Around Town Chukka Boot(
Women's) -
Huckleberry
    New
    Merrell Around Town Chukka Boot(
Women's) -
Brown Sugar
    Merrell Around Town Chukka Boot(
Women's) -
Sedona Sage
    $109.95
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    New!
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Black Soft Calf PU
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Dark Brown Tumble PU
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Tan Burnished Calf PU
    Sale
    $55.45
    $65.00 15% off
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    Stacy Adams Delaney Chukka Boot 25053 (Men's)
    New!
    Sale
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Black Burnished Leather/Suede
    New
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Brown Burnished Leather/Suede
    New
    Stacy Adams Delaney Chukka Boot 25053(
Men's) -
Cognac Burnished Leather/Suede
    New
    $104.95
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    The Freamon 2 eyelet Chukka Boot fuses athletic sensibilities with classic UGG® heritage details.Versatile, interchangeable 7mm Curly UGGpure™ and canvas ...
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