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Leather Mens Ankle Boots

1-36 of 428 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)
New!
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Amber Gold
Clarks Desert Boot(
                                      Men's) -
                                     Beeswax
Clarks Desert Boot(
                                      Men's) -
                                     Maple Suede
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Mustard Leather
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Sand SixtyFive 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) -
                                     Navy Leather
Clarks Desert Boot(
                                      Men's) -
                                     New Black Suede
Clarks Desert Boot(
                                      Men's) -
                                     Rust Leather
Clarks Desert Boot(
                                      Men's) -
                                     Sand Somerset
Clarks Desert Boot(
                                      Men's) -
                                     Taupe Distressed Suede
Clarks Desert Boot(
                                      Men's) -
                                     Terracotta Suede
Clarks Desert Boot(
                                      Men's) -
                                     White Leather
$45.45 - $180.45
$130.00 - $400.00 up to 65% 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
Clarks Montacute Lord (Men's)
Clarks Montacute Lord (Men's)
Clarks Montacute Lord (Men's)
New!
Sale
Clarks Montacute Lord(
                                      Men's) -
                                     Brown Warm Lined Leather
Sale
Clarks Montacute Lord(
                                      Men's) -
                                     Dark Tan Leather
Sale
$48.95 - $139.95
$150.00 - $160.00 up to 69% off
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) -
                                     Black Smooth
Dr. Martens 1460 8-Eye Boot(
                                      Men's) -
                                     Black Nappa
Dr. Martens 1460 8-Eye Boot(
                                      Men's) -
                                     Cherry Red Arcadia
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
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
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
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
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
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
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
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
Dr. Martens 1460 8-Eye Boot
New!
Sale
Dr. Martens 1460 8-Eye Boot -
                                     Black Greasy
Dr. Martens 1460 8-Eye Boot -
                                     Black Python
Dr. Martens 1460 8-Eye Boot -
                                     Cherry Red Smooth
Sale
Dr. Martens 1460 8-Eye Boot -
                                     Green Smooth
Sale
Dr. Martens 1460 8-Eye Boot -
                                     Union Jack/Black Smooth
Sale
Dr. Martens 1460 8-Eye Boot -
                                     Black Smooth Mono
Dr. Martens 1460 8-Eye Boot -
                                     Grey Python
Dr. Martens 1460 8-Eye Boot -
                                     Navy Smooth Leather
Dr. Martens 1460 8-Eye Boot -
                                     White Smooth Mono
$99.99 - $139.95
$135.00 up to 26% 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) -
                                     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) -
                                     Dark Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Maple Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Rust Leather
$139.95
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
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 -
                                     Crazy Horse/Brown Gore/Gum Sole
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
Blundstone Super 550 Series Boot -
                                     Wheat/Brown Gore/Gum Sole
$179.95
UGG Neumel (Men's)
UGG Neumel (Men's)
UGG Neumel (Men's)
New!
Sale
UGG Neumel(
                                      Men's) -
                                     Chestnut
UGG Neumel(
                                      Men's) -
                                     China Tea
$139.95
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
$134.98
$145.00 7% off
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
Blundstone Dress Series Boot
New!
Sale
Blundstone Dress Series Boot -
                                     Black
Blundstone Dress Series Boot -
                                     Brown
Blundstone Dress Series Boot -
                                     Brown Crazy Horse
Blundstone Dress Series Boot -
                                     Burgundy
Blundstone Dress Series Boot -
                                     Rustic Black
Blundstone Dress Series Boot -
                                     Rustic Brown
Blundstone Dress Series Boot -
                                     Rustic Brown Brogue
$174.95
Frye Oliver Chukka (Men's)
Frye Oliver Chukka (Men's)
New!
Sale
Frye Oliver Chukka(
                                      Men's) -
                                     Dark Brown Leather
Sale
$139.95
$278.00 50% off
Polo Ralph Lauren Conquest Hi III Boot (Men's)
Polo Ralph Lauren Conquest Hi III Boot (Men's)
Polo Ralph Lauren Conquest Hi III Boot (Men's)
Polo Ralph Lauren Conquest Hi III Boot (Men's)
Polo Ralph Lauren Conquest Hi III Boot (Men's)
New!
Sale
Polo Ralph Lauren Conquest Hi III Boot(
                                      Men's) -
                                     Dark Brown Silky Nubuck
Sale
Polo Ralph Lauren Conquest Hi III Boot(
                                      Men's) -
                                     Dark Grey Silky Nubuck
Sale
Polo Ralph Lauren Conquest Hi III Boot(
                                      Men's) -
                                     New Snuff Silky Nubuck
Sale
Polo Ralph Lauren Conquest Hi III Boot(
                                      Men's) -
                                     Polo Tan Burnished Leather
$119.99 - $148.95
$149.00 up to 19% 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
Clarks Desert Trek Boot (Men's)
Clarks Desert Trek Boot (Men's)
Clarks Desert Trek Boot (Men's)
Clarks Desert Trek Boot (Men's)
Clarks Desert Trek Boot (Men's)
Clarks Desert Trek Boot (Men's)
New!
Sale
Clarks Desert Trek Boot(
                                      Men's) -
                                     Beeswax
Clarks Desert Trek Boot(
                                      Men's) -
                                     Beeswax Leather
Sale
Clarks Desert Trek Boot(
                                      Men's) -
                                     Blue/Grey Leather
Clarks Desert Trek Boot(
                                      Men's) -
                                     Bronze/Brown Leather
Clarks Desert Trek Boot(
                                      Men's) -
                                     Travel Trek Leather
$90.45 - $149.95
$120.00 - $150.00 up to 25% off
Born Hemlock (Men's)
Born Hemlock (Men's)
Born Hemlock (Men's)
New!
Sale
Born Hemlock(
                                      Men's) -
                                     Castagno Full Grain Leather
Born Hemlock(
                                      Men's) -
                                     Chestnut Full Grain Leather
$109.95
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
Dr. Martens 2976 Chelsea Boot
Dr. Martens 2976 Chelsea Boot
New!
Sale
Dr. Martens 2976 Chelsea Boot -
                                     Grey Mare Waterproof Hi Suede
New
Dr. Martens 2976 Chelsea Boot -
                                     Khaki Waterproof Hi Suede
New
Dr. Martens 2976 Chelsea Boot -
                                     Aztec Rugged Crazy Horse
Dr. Martens 2976 Chelsea Boot -
                                     Black Inuck
Dr. Martens 2976 Chelsea Boot -
                                     Black Smooth
Dr. Martens 2976 Chelsea Boot -
                                     Cherry Red Smooth
Dr. Martens 2976 Chelsea Boot -
                                     Milkshake Waterproof Hi Suede
New
Dr. Martens 2976 Chelsea Boot -
                                     Navy Waterproof Hi Suede
New
$129.95 - $144.95
Merrell Annex Mid GORE-TEX (Men's)
Merrell Annex Mid GORE-TEX (Men's)
Merrell Annex Mid GORE-TEX (Men's)
Merrell Annex Mid GORE-TEX (Men's)
Merrell Annex Mid GORE-TEX (Men's)
New!
Sale
Merrell Annex Mid GORE-TEX(
                                      Men's) -
                                     Blue Wing
Merrell Annex Mid GORE-TEX(
                                      Men's) -
                                     Castle Rock
Merrell Annex Mid GORE-TEX(
                                      Men's) -
                                     Clay
Merrell Annex Mid GORE-TEX(
                                      Men's) -
                                     Light Beige
$179.95
Red Wing Blacksmith 6
Red Wing Blacksmith 6
Red Wing Blacksmith 6
Red Wing Blacksmith 6
New!
Sale
Red Wing Blacksmith 6
Red Wing Blacksmith 6
Red Wing Blacksmith 6
$299.95
Dr. Martens Pascal 8-Eye Boot
Dr. Martens Pascal 8-Eye Boot
Dr. Martens Pascal 8-Eye Boot
Dr. Martens Pascal 8-Eye Boot
Dr. Martens Pascal 8-Eye Boot
New!
Sale
Dr. Martens Pascal 8-Eye Boot -
                                     Cherry Red Antique Temperley
New
Dr. Martens Pascal 8-Eye Boot -
                                     Charcoal Antique Temperley
Dr. Martens Pascal 8-Eye Boot -
                                     Navy Antique Temperley
Dr. Martens Pascal 8-Eye Boot -
                                     White/Black Painter Leather
$129.95 - $134.95
Giorgio Brutini Genuine Kidskin 80575 (Men's)
Giorgio Brutini Genuine Kidskin 80575 (Men's)
Giorgio Brutini Genuine Kidskin 80575 (Men's)
Giorgio Brutini Genuine Kidskin 80575 (Men's)
Giorgio Brutini Genuine Kidskin 80575 (Men's)
Giorgio Brutini Genuine Kidskin 80575 (Men's)
New!
Sale
Giorgio Brutini Genuine Kidskin 80575(
                                      Men's) -
                                     Black
Giorgio Brutini Genuine Kidskin 80575(
                                      Men's) -
                                     Cream
Giorgio Brutini Genuine Kidskin 80575(
                                      Men's) -
                                     Dark Brown
Giorgio Brutini Genuine Kidskin 80575(
                                      Men's) -
                                     Navy
Giorgio Brutini Genuine Kidskin 80575(
                                      Men's) -
                                     Red
$84.95
Rockport Elkhart (Men's)
Rockport Elkhart (Men's)
Rockport Elkhart (Men's)
Rockport Elkhart (Men's)
New!
Sale
Rockport Elkhart(
                                      Men's) -
                                     Black Leather
Rockport Elkhart(
                                      Men's) -
                                     Chocolate Leather
Rockport Elkhart(
                                      Men's) -
                                     Dark Brown Leather
$134.95 - $149.95
Dr. Martens Vegan 1460 8-Eye Boot
Dr. Martens Vegan 1460 8-Eye Boot
Dr. Martens Vegan 1460 8-Eye Boot
Dr. Martens Vegan 1460 8-Eye Boot
New!
Sale
Dr. Martens Vegan 1460 8-Eye Boot -
                                     Black Felix Rub Off
Dr. Martens Vegan 1460 8-Eye Boot -
                                     Cherry Red Cambridge Brush
Dr. Martens Vegan 1460 8-Eye Boot -
                                     Hot Pink Cambridge Brush
$129.95
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)
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