Men's Boots & Chukkas

Displaying 462 items
Paul Stuart TAN Textured Leather Ankle Boots
Paul Stuart
$795.00
$279.97
65% Off
Original Penguin TAN Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% 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
Johnston & Murphy TAN Lofting Leather Gore Boots
Johnston & Murphy
$298.00
$149.99
50% Off
Ben Sherman TAN Faux Leather Ankle Boots
Ben Sherman
$110.00
$49.99
55% Off
Ben Sherman TAN Brent Leather Boots
Ben Sherman
$150.00
$69.99
53% Off
Sorel ELK Ankeny Leather Hiking Boots
Sorel
$140.00
$89.99
36% Off
Boss Hugo Boss DARK BROWN Leather Chelsea Boots
Boss Hugo Boss
$445.00
$239.99
46% Off
Ben Sherman DARK BROWN Gabe Leather Chukka Boots
Ben Sherman
$130.00
$69.99
46% Off
Saks Fifth Avenue DARK BROWN Baylor Leather Boots
Saks Fifth Avenue
$99.99
Johnston & Murphy DARK BROWN Fullerton Chukka Boots
Johnston & Murphy
$185.00
$89.99
51% Off
Bruno Magli DARK BROWN Leather Chelsea Boots
Bruno Magli
$460.00
$149.99
67% Off
UGG Australia BLACK UGG Zetik Waterproof Leather Boot
UGG Australia
$115.00
$89.99
22% Off
Sperry TAUPE Windsor Suede Lace-Up Boots
Sperry
$220.00
$119.99
45% Off
Nettleton TAUPE Suede Chelsea Boots
Nettleton
$595.00
$199.99
66% Off
UGG Australia BROWN UGG Camino Suede Chelsea Boot
UGG Australia
$140.00
$109.99
21% Off
UGG Australia BROWN UGG Camino Suede Chukka Boot
UGG Australia
$135.00
$109.99
19% Off
Mezlan BLUE MULTI 18769 Leather & Suede Wingtip Boots
Mezlan
$450.00
$159.97-$229.99
Up to 64% Off
Saks Fifth Avenue SAND Roma Suede Chelsea Boots
Saks Fifth Avenue
$99.99
$69.99
30% Off
Camper BROWN Camper Camper Neuman Ankle Boot
Camper
$195.00
$109.99
44% Off
Salvatore Ferragamo BLUE Salvatore Ferragamo Suede Boot
Salvatore Ferragamo
$660.00
$179.99
73% Off
Roberto Cavalli CAMEL Suede Chelsea Boots
Roberto Cavalli
$675.00
$249.99
63% Off
Cole Haan CHESTNUT Nathan Cap-Toe Leather Boots
Cole Haan
$250.00
$99.99
60% Off
Ben Sherman NAVY BLUE Omega Chukka Boots
Ben Sherman
$130.00
$59.99
54% Off
Saks Fifth Avenue MEDIUM BROWN Arrezzo Wingtip Leather Ankle Boots
Saks Fifth Avenue
$99.99
$69.99
30% Off
Antonio Maurizi BROWN Antonio Maurizi Suede Chelsea Boot
Antonio Maurizi
$535.00
$205.99
61% Off
Kenneth Cole REACTION BROWN Round-Toe Leather Ankle Boots
Kenneth Cole REACTION
$158.00
$69.99
56% Off
Pajar Canada BLACK Tour Waterproof Leather Boots
Pajar Canada
$175.00
$69.99
60% Off
Pajar Canada BROWN Tour Waterproof Leather Boots
Pajar Canada
$175.00
$69.99
60% Off
Pajar Canada COGNAC Tour Pebbled Leather Side-Zip Boots
Pajar Canada
$175.00
$69.99
60% Off
To Boot New York BROWN Athens Suede Ankle Boots
To Boot New York
$450.00
$229.99
49% Off
Diesel BLACK D-Vibe Leather Hiking Boots
Diesel
$248.00
$90.99
63% Off
Diesel GREY D-Cage Leather Combat Boots
Diesel
$298.00
$104.99
65% 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
$275.00
$99.99
64% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$89.99
65% Off
Timberland CHESTNUT Bardstown Leather Chukka Boots
Timberland
$350.00
$169.99
51% Off
Timberland RUM RAISIN American Craft Moc-Toe Leather Boots
Timberland
$350.00
$169.99
51% Off
Timberland CASTLEROCK Bardstown Leather Chukka Boots
Timberland
$350.00
$169.99
51% Off
Timberland BLACK American Craft Leather Combat Boots
Timberland
$350.00
$169.99
51% Off
Timberland DARK BROWN American Craft Leather Boots
Timberland
$350.00
$169.99
51% Off
Diesel SUNSHINE Leather Hiking Boots
Diesel
$248.00
$90.99
63% Off
Cole Haan BLACK Conway Waterproof Chelsea Boots
Cole Haan
$300.00
$99.99-$159.99
Up to 67% Off
Warfield & Grand BLACK Warfield & Grand Market Leather Boot
Warfield & Grand
$235.00
$99.99
57% Off
Antonio Maurizi BLACK Antonia Maurizi Suede Boot
Antonio Maurizi
$535.00
$199.00
63% Off
Cole Haan SLATE BLUE Zerogrand Suede Boots
Cole Haan
$250.00
$83.99
66% Off
Steve Madden DARK TAN Morris Cap-Toe Leather Boots
Steve Madden
$120.00
$79.99
33% Off
To Boot New York SIENNA Brighton Suede Ankle Chelsea Boots
To Boot New York
$425.00
$149.99
65% Off
Salvatore Ferragamo BLACK Salvatore Ferragamo Bankley Suede Ankle Boot
Salvatore Ferragamo
$1,290.00
$949.99
26% Off
Vince FLINT Brunswick Suede Chukka Boots
Vince
$350.00
$189.99
46% Off
Sorel BLACK Cheyanne II Short Waterproof Boots
Sorel
$135.00
$69.99-$89.99
Up to 48% Off
Salvatore Ferragamo BLACK Salvatore Ferragamo Twist Gancini Leather Ankle Boot
Salvatore Ferragamo
$1,090.00
$759.99
30% Off
Original Penguin SHIITAKE Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
Bruno Magli ROASTED DARK BROWN Cardone Leather & Suede Boots
Bruno Magli
$520.00
$229.99
56% Off
Belstaff BURNISHED Attwell Burnished Leather Boots
Belstaff
$575.00
$279.97
51% Off
Pajar Canada COGNAC NAVY Pete Lace Up Boots
Pajar Canada
$165.00
$69.97
58% Off
Giuseppe Zanotti LAVA Cap-Toe Chelsea Boots
Giuseppe Zanotti
$995.00
$499.99
50% Off
Karl Lagerfeld Paris BLACK Leather & Sock Chelsea Boots
Karl Lagerfeld Paris
$250.00
$149.99
40% Off
Bruno Magli BLACK Fedro Leather & Suede Wingtip Boots
Bruno Magli
$520.00
$229.99
56% Off
COLE HAAN GRAND OS WOODBURY Zerogrand Hiker II Leather Boots
COLE HAAN GRAND OS
$300.00
$99.99
67% Off
To Boot New York CACAO Brighton Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Original Penguin COGNAC Jaden Leather Boots
Original Penguin
$230.00
$99.99
57% Off
Saks Fifth Avenue BLACK Leather Chelsea Boots
Saks Fifth Avenue
$169.99
Rush by Gordon Rush BROWN Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$250.00
$88.00
65% Off
John Varvatos Star U.S.A. CHARCOAL Star Leather Chelsea Boots
John Varvatos Star U.S.A.
$298.00
$99.99
66% Off
Karl Lagerfeld Paris BLACK Leather Chelsea Boots
Karl Lagerfeld Paris
$375.00
$119.99
68% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Chelsea Boot
Rush by Gordon Rush
$250.00
$92.00
63% Off
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