Men's Boots & Chukkas

Displaying 260 items
Kenneth Cole REACTION BROWN Round-Toe Leather Ankle Boots
Kenneth Cole REACTION
$158.00
$69.99
56% Off
Ben Sherman BROWN Classic Leather Boots
Ben Sherman
$145.00
$53.97
63% Off
Steve Madden BLACK Leather Buckle Boots
New!
Steve Madden
$140.00
$99.99
29% Off
Ben Sherman TAN Brent Leather Boots
New!
Ben Sherman
$150.00
$79.99
47% Off
Original Penguin BROWN Lex Leather Ankle Boots
Original Penguin
$170.00
$54.97
68% Off
Saks Fifth Avenue BLACK Suede Wingtip Boots
Saks Fifth Avenue
$398.00
$135.99
66% Off
Magnanni GREY Leather Chukka Boots
New!
Magnanni
$495.00
$249.99
49% Off
Giuseppe Zanotti BROWN Suede Chukka Boots
Giuseppe Zanotti
$995.00
$499.99
50% Off
Mezlan BROWN Brogue Leather Boots
Mezlan
$450.00
$159.97
64% Off
Pajar Canada BROWN Tour Waterproof Leather Boots
Pajar Canada
$175.00
$104.99
40% Off
Pajar Canada BROWN Larry Suede Hiking Boots
Pajar Canada
$185.00
$49.97-$52.97
Up to 73% Off
Saks Fifth Avenue Made in Italy TAN Buckle-Strap Suede Chelsea Boots
New!
Saks Fifth Avenue Made in Italy
$169.99
Boss Hugo Boss BLACK Side-Zip Leather Chelsea Boots
New!
Boss Hugo Boss
$298.00
$159.99
46% Off
COLE HAAN GRAND OS BLACK ZeroGrand Rugged Leather Chukka Boots
COLE HAAN GRAND OS
$300.00
$139.99
53% Off
Bruno Magli BLACK Fedro Leather & Suede Wingtip Boots
New!
Bruno Magli
$520.00
$229.99
56% Off
The Frye Company COGNAC Essex Chelsea Shearling
The Frye Company
$298.00
$109.00
63% Off
Saks Fifth Avenue BLACK Rimini Eye Leather Chukka Boots
Saks Fifth Avenue
$200.00
$99.99
50% Off
G.H. Bass & Co. Factory Outlet BLACK Wren Boot
Comparable Value
$110.00
$69.99
36% 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
The Frye Company DARK BROWN Corey Lace Up
The Frye Company
$258.00
$149.00
42% Off
Original Penguin TAN Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
Saks Fifth Avenue TAN Roma Suede Chelsea Boots
Saks Fifth Avenue
$99.99
$74.99-$99.99
25% Off
Massimo Matteo TAN Buckled Leather Chelsea Boots
Massimo Matteo
$295.00-$325.00
$104.99-$149.99
Up to 68% Off