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Mens Chukka Boots

1-36 of 234 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 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) -
                                     Beeswax/Beeswax Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Black/Black Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Black/Black Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Bronze/Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Brown Tumbled Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Dark Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Leaf Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Maple Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Rust Leather
$139.95
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
Clarks Senner Drive (Men's)
Clarks Senner Drive (Men's)
New!
Sale
Clarks Senner Drive(
                                      Men's) -
                                     Chocolate Nubuck
Sale
$67.45
$100.00 33% 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
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
New!
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Tan Leather
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Taupe Nubuck
Sale
$90.95 - $109.95
$120.00 up to 24% off
Born Harrison (Men's)
Born Harrison (Men's)
Born Harrison (Men's)
Born Harrison (Men's)
New!
Sale
Born Harrison(
                                      Men's) -
                                     Castagno Full Grain Leather
Born Harrison(
                                      Men's) -
                                     Chestnut Full Grain Leather
Born Harrison(
                                      Men's) -
                                     Peltro Full Grain Leather
$109.95
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
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
New!
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Beeswax Leather
Clarks Stinson Hi(
                                      Men's) -
                                     Black Oily Leather
Clarks Stinson Hi(
                                      Men's) -
                                     Charcoal Grey Suede
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Chocolate Brown Suede
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Navy Cow Suede
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Black Suede
Clarks Stinson Hi(
                                      Men's) -
                                     Brown Oily Leather
Clarks Stinson Hi(
                                      Men's) -
                                     Grey/Grey Suede
Clarks Stinson Hi(
                                      Men's) -
                                     Sand Suede
$71.45 - $99.95
$100.00 up to 29% 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
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) -
                                     Navy Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Tan Leather
Sale
$89.95
$100.00 10% 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
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
Naot Pilot (Men's)
Naot Pilot (Men's)
Naot Pilot (Men's)
Naot Pilot (Men's)
Naot Pilot (Men's)
New!
Sale
Naot Pilot(
                                      Men's) -
                                     Blue Velvet Suede
Naot Pilot(
                                      Men's) -
                                     Gray Suede
Naot Pilot(
                                      Men's) -
                                     Seal Brown Suede
Naot Pilot(
                                      Men's) -
                                     Vintage Grey Leather
$199.95
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
Steve Madden Harken Chukka (Men's)
Steve Madden Harken Chukka (Men's)
Steve Madden Harken Chukka (Men's)
New!
Sale
Steve Madden Harken Chukka(
                                      Men's) -
                                     Black  Leather
Steve Madden Harken Chukka(
                                      Men's) -
                                     Cognac Leather
$84.95 - $89.95
Stacy Adams Trickster Moc Toe Chukka Boot 53419 (Men's)
Stacy Adams Trickster Moc Toe Chukka Boot 53419 (Men's)
Stacy Adams Trickster Moc Toe Chukka Boot 53419 (Men's)
Stacy Adams Trickster Moc Toe Chukka Boot 53419 (Men's)
Stacy Adams Trickster Moc Toe Chukka Boot 53419 (Men's)
New!
Sale
Stacy Adams Trickster Moc Toe Chukka Boot 53419(
                                      Men's) -
                                     Black PU
Stacy Adams Trickster Moc Toe Chukka Boot 53419(
                                      Men's) -
                                     Brown PU
Stacy Adams Trickster Moc Toe Chukka Boot 53419(
                                      Men's) -
                                     Cognac PU
Stacy Adams Trickster Moc Toe Chukka Boot 53419(
                                      Men's) -
                                     Navy PU
$74.95
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
New!
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Brown Smooth Leather
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Brown Suede
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Sand Suede
Sale
$68.00
$75.00 9% off