Men's Boots & Chukkas

Displaying 250 items
Kenneth Cole New York RUST Distressed Suede Chelsea Boots
Kenneth Cole New York
$150.00
$62.99
58% Off
Stella McCartney RED BLACK Leather Chelsea Boots
Stella McCartney
$745.00
$389.97
48% Off
Karl Lagerfeld Paris BLACK Buckled Leather Ankle Boots
Karl Lagerfeld Paris
$375.00-$450.00
$129.99
Up to 71% Off
Karl Lagerfeld Paris BLACK Leather Chelsea Boots
Karl Lagerfeld Paris
$375.00
$119.99
68% Off
Kenneth Cole REACTION BLACK Round-Toe Leather Ankle Boots
Kenneth Cole REACTION
$158.00
$69.99
56% Off
COLE HAAN GRAND OS BLACK ZeroGrand Rugged Leather Chukka Boots
COLE HAAN GRAND OS
$300.00
$139.99
53% Off
John Galliano BLACK Lamb Fur-Trim Leather Boots
John Galliano
$640.00
$249.99
61% Off
Saks Fifth Avenue LIGHT TAUPE Monterosa Suede Outdoor Boots
Saks Fifth Avenue
$99.99
$55.97
44% Off
Original Penguin SHIITAKE Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
To Boot New York BLACK Brighton Chelsea Boots
To Boot New York
$425.00
$151.99-$199.99
Up to 64% Off
Pajar Canada COGNAC NAVY Pete Lace Up Boots
Pajar Canada
$165.00
$69.97
58% Off
Pajar Canada DARK NIGHT Larry Suede Hiking Boots
Pajar Canada
$185.00
$49.97-$52.97
Up to 73% Off
Roberto Cavalli CAMEL Suede Chelsea Boots
Roberto Cavalli
$675.00
$249.99
63% Off
G.H. Bass & Co. Factory Outlet TAN Broker Leather Boot
Comparable Value
$145.00-$170.00
$99.99
Up to 41% Off
Saks Fifth Avenue BLACK Suede Wingtip Boots
Saks Fifth Avenue
$398.00
$135.99
66% Off
Saks Fifth Avenue COGNAC Brickley Suede Chelsea Boots
Saks Fifth Avenue
$398.00
$135.99
66% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Louie Duck Boot
Comparable Value
$130.00
$84.99
35% Off
Robert Graham BLACK Metropolis Leather Chelsea Boots
New!
Robert Graham
$278.00
$109.99
60% Off
Swims GREY Motion Chukka Boots
Swims
$250.00
$119.99
52% Off
Karl Lagerfeld Paris BLACK Faux Fur-Lined Leather Boots
Karl Lagerfeld Paris
$400.00
$129.99
68% Off
Jo Ghost BLACK Leather Zip Boots
Jo Ghost
$550.00
$189.97
65% Off
Paul Stuart GREY Lace-Up Suede Hiker Boots
Paul Stuart
$695.00
$244.97
65% Off
Bruno Magli GREY Classic Suede Chelsea Boots
Bruno Magli
$520.00
$153.99
70% Off
Original Penguin BROWN Lex Leather Ankle Boots
Original Penguin
$170.00
$54.97
68% Off
Ben Sherman BROWN Classic Leather Boots
Ben Sherman
$145.00
$53.97
63% Off
Paul Stuart TAN Textured Leather Ankle Boots
Paul Stuart
$795.00
$279.97
65% Off
To Boot New York TAN Bandon Suede Chelsea Boots
To Boot New York
$395.00
$119.97
70% Off
Original Penguin TAN Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off