Men's Boots & Chukkas

Displaying 452 items
Aquatalia GREY Irus Leather & Mesh Lace-Up Boots
Aquatalia
$595.00
$249.99
58% Off
Diesel GREY D-Cage Leather Combat Boots
Diesel
$298.00
$104.99
65% Off
Pajar Canada BROWN Tour Waterproof Leather Boots
Pajar Canada
$175.00
$69.99
60% Off
Massimo Matteo BROWN Buckled Leather Chelsea Boots
Massimo Matteo
$295.00
$99.99
66% Off
Jo Ghost BROWN Almond Toe Leather Ankle Boots
Jo Ghost
$525.00
$174.99-$249.99
Up to 67% Off
Sperry BROWN Windsor Leather Loafer Boots
Sperry
$220.00
$119.99
45% Off
Nettleton BROWN Suede Chelsea Boots
Nettleton
$595.00
$199.99
66% Off
Aquatalia BROWN Heath Suede Hiking Boots
Aquatalia
$595.00
$249.99
58% Off
Aquatalia BROWN Vladimir Suede Ankle Boots
Aquatalia
$595.00
$174.99-$249.99
Up to 71% Off
Jo Ghost BROWN Lizard-Embossed Leather Boots
Jo Ghost
$525.00
$249.99
52% Off
Aquatalia BROWN William Suede Boots
Aquatalia
$550.00
$249.99
55% Off
Aquatalia BROWN Christopher Suede Hiking Boots
Aquatalia
$595.00
$249.99
58% Off
Sorel BROWN Ankeny Leather Hiking Boots
Sorel
$140.00
$89.99
36% Off
To Boot New York BROWN Rosemont Leather Boots
To Boot New York
$398.00
$199.99
50% Off
Vince BROWN Novato Leather Chukka Boots
Vince
$350.00
$164.97
53% Off
Aquatalia BROWN Adrian Leather Chelsea Boots
Aquatalia
$450.00
$219.99
51% Off
Original Penguin TAN Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
Sutor Mantellassi BROWN Peleo Leather Boots
Sutor Mantellassi
$815.00
$295.99
64% Off
Mezlan BROWN Brogue Leather Boots
Mezlan
$450.00
$159.97
64% Off
Cole Haan BRITISH TAN Conway Waterproof Chelsea Boots
Cole Haan
$300.00
$99.99-$159.99
Up to 67% Off
Original Penguin BLACK Jaden Leather Boots
Original Penguin
$230.00
$114.99
50% Off
Timberland BLACK American Craft Leather Combat Boots
Timberland
$350.00
$169.99
51% Off
Mezlan BLACK Higgins Leather Boots
Mezlan
$450.00
$229.99
49% Off
Mezlan BLACK Essen Leather Ankle Boots
Mezlan
$395.00
$199.99
49% Off
Jo Ghost BLACK Shearling-Lined Leather Boots
Jo Ghost
$555.00
$279.99
50% Off
Jo Ghost BLACK Laced Leather Boots
Jo Ghost
$575.00
$259.99
55% Off
Johnston & Murphy DARK BROWN Fullerton Chukka Boots
Johnston & Murphy
$185.00
$89.99
51% Off
Johnston & Murphy DARK BROWN Bryson Side-Zip Chelsea Boots
Johnston & Murphy
$298.00
$149.99
50% Off
Saks Fifth Avenue DARK BROWN Baylor Leather Boots
Saks Fifth Avenue
$99.99
Ben Sherman DARK BROWN Gabe Leather Chukka Boots
Ben Sherman
$130.00
$69.99
46% Off
Aquatalia BURGUNDY Waterproof Leather Boots
Aquatalia
$595.00
$249.99
58% Off
Sorel ELK Ankeny Leather Hiking Boots
Sorel
$140.00
$69.99
50% Off
Sperry TAUPE Windsor Suede Lace-Up Boots
Sperry
$220.00
$119.99
45% Off
Ben Sherman TAN Faux Leather Ankle Boots
Ben Sherman
$110.00
$49.99
55% Off
Vince FLINT Aldous Suede Boots
Vince
$395.00
$189.99
52% Off
Ben Sherman NAVY BLUE Omega Chukka Boots
Ben Sherman
$130.00
$59.99
54% Off
Original Penguin SHIITAKE Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
UGG Australia BLACK UGG Biltmore Moto Leather Boot
UGG Australia
$170.00
$135.99
20% Off
UGG Australia BLACK UGG Tahoe Leather Boot
UGG Australia
$225.00
$179.99
20% Off
Saks Fifth Avenue BLACK Rimini Eye Leather Chukka Boots
Saks Fifth Avenue
$200.00
$99.99
50% Off
Donald Pliner BLACK Donald Pliner Mark Leather Boot
Donald Pliner
$295.00
$39.00
87% Off
Warfield & Grand BLACK Warfield & Grand Crest Leather Boot
Warfield & Grand
$235.00
$95.99
59% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$89.99
65% Off
UGG Australia BLACK UGG Butte Waterproof Leather & Suede Boot
UGG Australia
$225.00
$179.99
20% Off
Steve Madden COGNAC Yearn Leather Chelsea Boots
Steve Madden
$140.00
$69.99
50% Off
UGG Australia BLACK UGG Morrison Pull-On Leather Boot
UGG Australia
$200.00
$159.99
20% Off
Kenneth Cole New York COGNAC Class 2.0 Leather Ankle Boots
Kenneth Cole New York
$175.00
$69.99
60% Off
Saks Fifth Avenue SAND Roma Suede Chelsea Boots
Saks Fifth Avenue
$99.99
$69.99
30% Off
Sorel BLACK Cheyanne II Short Waterproof Boots
Sorel
$135.00
$69.99-$89.99
Up to 48% Off
Warfield & Grand BLUE Warfield & Grand Keystone Suede Boot
Warfield & Grand
$225.00
$89.99
60% Off
Original Penguin BLACK Original Penguin Shane Leather Boot
Original Penguin
$200.00
$99.99
50% Off
Church's BLUE Church's Ryder 3 Suede Boot
Church's
$595.00
$249.99
58% Off
Original Penguin BROWN Original Penguin Samson Suede Chelsea Boot
Original Penguin
$160.00
$99.99
38% Off
Steve Madden BLACK Leather Buckle Boots
Steve Madden
$140.00
$69.99
50% Off
Frye RED Frye Greyson Leather Boot
Frye
$428.00
$119.99
72% Off
Saks Fifth Avenue Made in Italy TAN Buckle-Strap Suede Chelsea Boots
Saks Fifth Avenue Made in Italy
$169.99
$149.99
12% Off
Cole Haan CHESTNUT Nathan Cap-Toe Leather Boots
Cole Haan
$250.00
$99.99
60% Off
Cole Haan SLATE BLUE Zerogrand Suede Boots
Cole Haan
$250.00
$83.99
66% Off
Roberto Cavalli CAMEL Suede Chelsea Boots
Roberto Cavalli
$675.00
$249.99
63% Off
Jo Ghost WOOD Suede Leather Boots
Jo Ghost
$529.00
$249.99
53% Off
Karl Lagerfeld Paris BLACK Faux Fur-Lined Leather Boots
Karl Lagerfeld Paris
$395.00
$129.99
67% Off
To Boot New York CACAO Brighton Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Steve Madden BLACK Irving Chelsea Boots
Steve Madden
$120.00
$79.99
33% Off
Salvatore Ferragamo BLUE Salvatore Ferragamo Suede Boot
Salvatore Ferragamo
$660.00
$179.99
73% Off
Cole Haan BLACK Nantucket Leather Boots
Cole Haan
$250.00
$139.99
44% Off
Bruno Magli BLACK Fedro Leather & Suede Wingtip Boots
Bruno Magli
$520.00
$229.99
56% Off
Mezlan COGNAC Essen Leather Boots
Mezlan
$395.00
$199.99
49% Off
John Varvatos Star U.S.A. CHARCOAL Star Leather Chelsea Boots
John Varvatos Star U.S.A.
$298.00
$99.99
66% Off
Johnston & Murphy TAUPE Cormac Suede Chukka Boots
Johnston & Murphy
$299.00
$149.99
50% Off
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