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Leather Chukka Boots

1-36 of 105 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)
New!
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Amber Gold
Clarks Desert Boot(
                                      Men's) -
                                     Beeswax
Clarks Desert Boot(
                                      Men's) -
                                     Black Suede
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Black Smooth
Clarks Desert Boot(
                                      Men's) -
                                     Brown
Clarks Desert Boot(
                                      Men's) -
                                     Green Leather
Clarks Desert Boot(
                                      Men's) -
                                     Leaf Suede
Clarks Desert Boot(
                                      Men's) -
                                     New Black Suede
Clarks Desert Boot(
                                      Men's) -
                                     New Sand Suede
Clarks Desert Boot(
                                      Men's) -
                                     Rust Leather
Clarks Desert Boot(
                                      Men's) -
                                     Sand SixtyFive Suede
Clarks Desert Boot(
                                      Men's) -
                                     Taupe Distressed Suede
Clarks Desert Boot(
                                      Men's) -
                                     Terracotta Suede
$109.95 - $399.95
$130.00 - $400.00 up to 15% off
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
$149.95
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
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
New!
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Amber Harness Leather
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Charcoal Rough And Tough
Sale
$108.95 - $155.95
$310.00 up to 65% off
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)
ECCO Turn GORE-TEX Boot (Men's)
New!
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Black Lexi Leather
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Black Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Mocha Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Coffee Lexi Leather
$174.95 - $229.95
$230.00 up to 24% 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) -
                                     Espresso Nubuck
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Tan Full Grain Leather
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Wheat Nubuck
Sale
$109.95
$120.00 8% 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)
New!
Sale
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
Clarks Stratton Limit (Men's)
Clarks Stratton Limit (Men's)
Clarks Stratton Limit (Men's)
New!
Sale
Clarks Stratton Limit(
                                      Men's) -
                                     Black Leather
Clarks Stratton Limit(
                                      Men's) -
                                     Brown Leather
$134.95
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
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
$165.95
$207.00 20% off
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
New!
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
$157.95
$197.00 20% off
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
New!
Sale
Steve Madden Hestonn(
                                      Men's) -
                                     Dark Brown Leather
Steve Madden Hestonn(
                                      Men's) -
                                     Grey Leather
Steve Madden Hestonn(
                                      Men's) -
                                     Tan Leather
$84.95
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
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
Florsheim Rockit Chukka (Men's)
Florsheim Rockit Chukka (Men's)
Florsheim Rockit Chukka (Men's)
New!
Sale
Florsheim Rockit Chukka(
                                      Men's) -
                                     Black Distressed Milled Leather
Sale
Florsheim Rockit Chukka(
                                      Men's) -
                                     Brown Distressed Milled Leather
Sale
$101.95
$135.00 24% off
Born Jax (Men's)
Born Jax (Men's)
Born Jax (Men's)
Born Jax (Men's)
Born Jax (Men's)
New!
Sale
Born Jax(
                                      Men's) -
                                     Black Full Grain Leather
Born Jax(
                                      Men's) -
                                     Brown Full Grain Leather
Born Jax(
                                      Men's) -
                                     Dijon Suede
Born Jax(
                                      Men's) -
                                     Tan Full Grain Leather
$108.95 - $109.95
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)
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
Florsheim Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
New!
Sale
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Black Leather
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Brown Leather
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Cognac Leather
$119.95
Mark Nason Skechers Elmwood (Men's)
Mark Nason Skechers Elmwood (Men's)
New!
Sale
Mark Nason Skechers Elmwood(
                                      Men's) -
                                     Black
Sale
$99.95
$124.00 19% off
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) -
                                     Gray Leather
Eastland Seneca(
                                      Men's) -
                                     Peanut Leather
Eastland Seneca(
                                      Men's) -
                                     Tan Waxee Leather
$99.95 - $109.95
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
New!
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Anthracite Matte Metallic Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Black Sofia Crust Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Bronze Matte Metallic Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Dark Blue Box Leather
Sale
$97.95
$139.00 30% off
Boston Boot Co. Newbury Chukka Boot (Men's)
Boston Boot Co. Newbury Chukka Boot (Men's)
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
$173.95
$217.00 20% off
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
New!
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Black Full Grain Leather
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Cafe Full Grain Leather
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Tierra Full Grain Leather
Sale
$98.95
$129.00 23% off