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Leather Mens Ankle Boots

1-36 of 481 results
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Eastland Brooklyn (Men's)
Eastland Brooklyn (Men's)
Eastland Brooklyn (Men's)
New!
Sale
Eastland Brooklyn(
Men's) -
Black Leather
Sale
Eastland Brooklyn(
Men's) -
Burgundy Leather
Sale
$62.00
$115.00 46% 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)
Johnston & Murphy Copeland Chukka Boot (Men's)
New!
Sale
Johnston & Murphy Copeland Chukka Boot(
Men's) -
Taupe Water-Resistant Suede
New
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 - $154.95
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) -
Sand Somerset
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) -
Navy Leather
Clarks Desert Boot(
Men's) -
New Black Suede
Clarks Desert Boot(
Men's) -
Rust Leather
Clarks Desert Boot(
Men's) -
Taupe Distressed Suede
$82.45 - $129.95
$130.00 up to 37% off
Stacy Adams Madison 00015 (Men's)
Stacy Adams Madison 00015 (Men's)
Stacy Adams Madison 00015 (Men's)
Stacy Adams Madison 00015 (Men's)
Stacy Adams Madison 00015 (Men's)
Stacy Adams Madison 00015 (Men's)
New!
Sale
Stacy Adams Madison 00015(
Men's) -
Black Kidskin
Stacy Adams Madison 00015(
Men's) -
Brown Kidskin
Stacy Adams Madison 00015(
Men's) -
Steel Grey Kidskin
Stacy Adams Madison 00015(
Men's) -
Taupe Kidskin Leather
Stacy Adams Madison 00015(
Men's) -
White Kidskin Leather
$134.95
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
Dr. Martens 1460 8-Eye Boot (Men's)
New!
Sale
Dr. Martens 1460 8-Eye Boot(
Men's) -
Aztec Crazy Horse
Dr. Martens 1460 8-Eye Boot(
Men's) -
Bark Grizzly
Dr. Martens 1460 8-Eye Boot(
Men's) -
Cherry Red Arcadia
Sale
Dr. Martens 1460 8-Eye Boot(
Men's) -
Black Smooth
Dr. Martens 1460 8-Eye Boot(
Men's) -
Black Nappa
Dr. Martens 1460 8-Eye Boot(
Men's) -
Cherry Red Smooth
Dr. Martens 1460 8-Eye Boot(
Men's) -
Green Smooth
Dr. Martens 1460 8-Eye Boot(
Men's) -
White Smooth
$124.95 - $134.95
$125.00 - $135.00 up to 7% off
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
Blundstone Original 500 Series Boot
New!
Sale
Blundstone Original 500 Series Boot -
Black
Blundstone Original 500 Series Boot -
Black/Grey Gore
Blundstone Original 500 Series Boot -
Brown/Multi
Blundstone Original 500 Series Boot -
Stout Brown
Blundstone Original 500 Series Boot -
Stout Brown/Burnt Orange
Blundstone Original 500 Series Boot -
Stout Brown/Olive Gore
Blundstone Original 500 Series Boot -
Stout Brown/Orange Gore
$169.95
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)
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
$84.95
$99.00 14% off
Dr. Martens Heritage Ironbridge Steel Toe 8 Tie Boot
Dr. Martens Heritage Ironbridge Steel Toe 8 Tie Boot
Dr. Martens Heritage Ironbridge Steel Toe 8 Tie Boot
New!
Sale
Dr. Martens Heritage Ironbridge Steel Toe 8 Tie Boot -
Black Industrial Grizzly
Sale
Dr. Martens Heritage Ironbridge Steel Toe 8 Tie Boot -
Teak Industrial Trailblazer
Sale
$125.95
$145.00 13% off
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) -
Dark Green 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) -
Maple Suede
Clarks Wallabee Boot(
Men's) -
Rust Leather
$127.95 - $139.95
$140.00 up to 9% off
Merrell Moab Rover Mid Waterproof Boot (Men's)
Merrell Moab Rover Mid Waterproof Boot (Men's)
Merrell Moab Rover Mid Waterproof Boot (Men's)
Merrell Moab Rover Mid Waterproof Boot (Men's)
Merrell Moab Rover Mid Waterproof Boot (Men's)
New!
Sale
Merrell Moab Rover Mid Waterproof Boot(
Men's) -
Black
Merrell Moab Rover Mid Waterproof Boot(
Men's) -
Castle Rock
Merrell Moab Rover Mid Waterproof Boot(
Men's) -
Espresso
Merrell Moab Rover Mid Waterproof Boot(
Men's) -
Merrell Tan
$139.95
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
Dr. Martens 1460 8-Eye Boot 509566
New!
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Black Pebble
New
Dr. Martens 1460 8-Eye Boot 509566 -
Black Ajax
Dr. Martens 1460 8-Eye Boot 509566 -
Black Greasy
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Black Python
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Black Smooth Mono
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Cherry Red Smooth
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Green Smooth
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Grey Python
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Navy Smooth Leather
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
Union Jack/Black Smooth
Sale
Dr. Martens 1460 8-Eye Boot 509566 -
White Smooth Mono
$99.95 - $134.95
$125.00 - $135.00 up to 26% off
Dr. Martens Jadon 8-Eye Boot
Dr. Martens Jadon 8-Eye Boot
Dr. Martens Jadon 8-Eye Boot
New!
Sale
Dr. Martens Jadon 8-Eye Boot -
Black Polished Smooth
Dr. Martens Jadon 8-Eye Boot -
Cherry Red Polished Smooth
$169.95
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
Blundstone Super 550 Series Boot
New!
Sale
Blundstone Super 550 Series Boot -
Black
Blundstone Super 550 Series Boot -
Black/Red Gore/Red Sole
Blundstone Super 550 Series Boot -
Brown Crazy Horse
Blundstone Super 550 Series Boot -
Burgundy
Blundstone Super 550 Series Boot -
Moss/Olive Suede
Blundstone Super 550 Series Boot -
Navy
Blundstone Super 550 Series Boot -
Rustic Black
Blundstone Super 550 Series Boot -
Rustic Brown
Blundstone Super 550 Series Boot -
Rustic Brown/Brown Gore/Gum Sole
Blundstone Super 550 Series Boot -
Steel Grey/Black Gore
Blundstone Super 550 Series Boot -
Stout Brown/Olive
Blundstone Super 550 Series Boot -
Walnut
$179.95
Florsheim Duke (Men's)
Florsheim Duke (Men's)
Florsheim Duke (Men's)
New!
Sale
Florsheim Duke(
Men's) -
Cavello Kid Black
Florsheim Duke(
Men's) -
Cavello Kid Cognac
$134.95
Florsheim Essex (Men's)
Florsheim Essex (Men's)
Florsheim Essex (Men's)
New!
Sale
Florsheim Essex(
Men's) -
Black
Florsheim Essex(
Men's) -
Dark Cherry
$129.95
Merrell Moab Mid Waterproof (Men's)
Merrell Moab Mid Waterproof (Men's)
Merrell Moab Mid Waterproof (Men's)
Merrell Moab Mid Waterproof (Men's)
Merrell Moab Mid Waterproof (Men's)
New!
Sale
Merrell Moab Mid Waterproof(
Men's) -
Castle Rock/Black
Merrell Moab Mid Waterproof(
Men's) -
Dusty Olive/Black
Merrell Moab Mid Waterproof(
Men's) -
Olive
Merrell Moab Mid Waterproof(
Men's) -
Sedona Sage
$129.95
Stacy Adams Madison 00057 (Men's)
Stacy Adams Madison 00057 (Men's)
Stacy Adams Madison 00057 (Men's)
Stacy Adams Madison 00057 (Men's)
Stacy Adams Madison 00057 (Men's)
New!
Sale
Stacy Adams Madison 00057(
Men's) -
Black Leather
Stacy Adams Madison 00057(
Men's) -
Brown Leather
Stacy Adams Madison 00057(
Men's) -
Gray Leather
Stacy Adams Madison 00057(
Men's) -
Tan Leather
$144.95
Andrew Marc Hillcrest (Men's)
Andrew Marc Hillcrest (Men's)
New!
Sale
Andrew Marc Hillcrest(
Men's) -
Dark Brown/Dark Natural/Natural/Brown/Black Suede
Sale
$124.99
$248.00 50% off
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot (Men's)
New!
Sale
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot(
Men's) -
Burnt Maple
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot(
Men's) -
Grey
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot(
Men's) -
Merrell Tan
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot(
Men's) -
Olive
Merrell All Out Blaze Vent Mid Waterproof Hiking Boot(
Men's) -
Sodalite
$149.95
Mezlan Berne Chelsea Boot (Men's)
Mezlan Berne Chelsea Boot (Men's)
New!
Sale
Mezlan Berne Chelsea Boot(
Men's) -
Tan Suede
Sale
$252.95
$425.00 40% off
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
New!
Sale
Dr. Martens 2976 Chelsea Boot -
Aztec Rugged Crazy Horse
Dr. Martens 2976 Chelsea Boot -
Black Inuck
Dr. Martens 2976 Chelsea Boot -
Navy Waterproof Hi Suede
Sale
Dr. Martens 2976 Chelsea Boot -
Black Smooth
Dr. Martens 2976 Chelsea Boot -
Cherry Red Smooth
Dr. Martens 2976 Chelsea Boot -
Khaki Waterproof Hi Suede
$99.95 - $144.95
$130.00 - $145.00 up to 26% off