Men's Boots & Chukkas

Displaying 421 items
Robert Graham BLACK Dawson Floral-Embossed Chelsea Boots
Robert Graham
$268.00
$109.99
59% Off
Sorel BLACK Ankeny Mid-Hiking Boots
New!
Sorel
$140.00
$89.99
36% Off
Pajar Canada BLACK Tour Waterproof Leather Boots
Pajar Canada
$175.00
$104.99
40% Off
Pajar Canada BROWN Tour Waterproof Leather Boots
Pajar Canada
$175.00
$104.99
40% Off
Cole Haan BRITISH TAN Conway Waterproof Chelsea Boots
Cole Haan
$300.00
$159.99
47% Off
Original Penguin SHIITAKE Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
U.S. Polo Assn. TAN PARTT Camo Boot
$49.99
$39.99
20% Off
U.S. Polo Assn. BROWN TRINDLE Trindle Boot
$45.00
$39.99
11% Off
Bruno Magli DARK BROWN Leather Chelsea Boots
Bruno Magli
$460.00-$480.00
$219.99
Up to 54% Off
U.S. Polo Assn. BROWN PERRY Perry Boot
$45.00
$39.99
11% Off
Arche 42|77 Zorak Boots
$595.00
$298.00
50% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Radley Chukka Boot
Comparable Value
$140.00
$49.99
64% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Malcolm Lace-Up Boot
Comparable Value
$145.00
$59.99
59% Off
G.H. Bass & Co. Factory Outlet BLACK Russ Lace-up Boot
Comparable Value
$160.00
$69.99
56% Off
G.H. Bass & Co. Factory Outlet WHEAT Bolton Work Boot
Comparable Value
$180.00
$79.99
56% Off
G.H. Bass & Co. Factory Outlet BROWN COMBO Deacon Lace Up Boot
Comparable Value
$130.00
$69.99
46% Off
G.H. Bass & Co. Factory Outlet BROWN William Boot
Comparable Value
$130.00
$49.99
62% Off
G.H. Bass & Co. Factory Outlet BROWN COMBO Coleman Chukka Boot
Comparable Value
$120.00
$54.99
54% Off
G.H. Bass & Co. Factory Outlet BLACK Duxbury Plain Toe Boot
Comparable Value
$150.00
$99.99
33% Off
G.H. Bass & Co. Factory Outlet BROWN Buck 2.0 Knit Demi Boot
Comparable Value
$135.00
$79.99
41% Off
John Varvatos Star U.S.A. CHARCOAL Star Leather Chelsea Boots
John Varvatos Star U.S.A.
$298.00
$149.99
50% Off
G.H. Bass & Co. Factory Outlet TAUPE Trail Tour Hiking Boot
Comparable Value
$165.00
$89.99
45% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Duxbury Chukka Boot
New!
Comparable Value
$120.00
$99.99
17% Off
G.H. Bass & Co. Factory Outlet CHARCOAL Randall Chelsea Boot
Comparable Value
$140.00
$59.99
57% Off
Nautica GREY SHADOW Nautica Competiton Boots
New!
$70.00
$52.50
25% Off
Nautica BROWN STONE Lace Up Winter Boots
New!
$70.00
$52.50
25% Off
Roberto Cavalli CAMEL Suede Chelsea Boots
Roberto Cavalli
$675.00
$249.99
63% Off
Rush by Gordon Rush BROWN Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$109.99
58% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$89.99
65% Off
Steve Madden BLACK Irving Chelsea Boots
Steve Madden
$120.00
$79.99
33% Off
Cole Haan CHESTNUT Nathan Cap-Toe Leather Boots
Cole Haan
$250.00
$119.99
52% Off
Johnston & Murphy BROWN Shearling-Lined Leather Boots
New!
Johnston & Murphy
$225.00
$109.99
51% Off
Bally TOBACCO Suede & Leather Lace-Up Boots
New!
Bally
$695.00
$329.99
53% Off
Balenciaga NOIR Leather Lace-Up Combat Boots
Balenciaga
$1,295.00
$469.99
64% Off
Saks Fifth Avenue DARK BROWN Baylor Leather Boots
Saks Fifth Avenue
$99.99
Bruno Magli ROASTED DARK BROWN Cardone Leather & Suede Boots
Bruno Magli
$520.00
$229.99
56% Off
Mezlan COGNAC BROWN 18686 Tie Front Leather Chelsea Boots
Mezlan
$450.00
$159.97-$229.99
Up to 64% Off
Diesel SUNSHINE Leather Hiking Boots
Diesel
$248.00
$90.99
63% Off
Aquatalia DARK TAUPE Vladimir Suede Ankle Boots
Aquatalia
$595.00
$174.99-$249.99
Up to 71% Off
Steve Madden DARK TAN Morris Cap-Toe Leather Boots
Steve Madden
$120.00
$79.99
33% Off
Cole Haan MAHOGANY Watson Chukka II Leather Boots
Cole Haan
$250.00
$139.99
44% Off
To Boot New York SIENNA Brighton Suede Ankle Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Cole Haan MAJOR BROWN Waterproof Two-Tone Leather Boots
Cole Haan
$350.00
$126.99
64% Off
Cole Haan SLATE BLUE Zerogrand Suede Boots
Cole Haan
$250.00
$83.99
66% Off
To Boot New York CACAO Brighton Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Roberto Cavalli CUOTMORO Chelsea Leather Boots
Roberto Cavalli
$585.00
$249.99
57% 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
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$265.00
$109.99
58% Off
Warfield & Grand BROWN Warfield & Grand Garrison 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
$99.00
62% Off
G.H. Bass & Co. Factory Outlet BLACK Broker Leather Boot
Comparable Value
$145.00-$170.00
$89.99
Up to 47% Off
G.H. Bass & Co. Factory Outlet BROWN Radley Chukka Boot
Comparable Value
$140.00
$49.99
64% Off
G.H. Bass & Co. Factory Outlet TAN Malcolm Leather Boot
Comparable Value
$145.00
$69.99
52% Off
G.H. Bass & Co. Factory Outlet BLACK Peak Hiker Boot
Comparable Value
$140.00
$59.99
57% Off
G.H. Bass & Co. Factory Outlet TAN Flex Step Chukka Boot
Comparable Value
$165.00
$69.99
58% Off
G.H. Bass & Co. Factory Outlet CAMO Mallard Duck Boot
Comparable Value
$135.00
$69.99
48% Off
Mezlan BROWN Brogue Leather Boots
Mezlan
$450.00
$229.99
49% Off
Bruno Magli BLACK Fedro Leather & Suede Wingtip Boots
Bruno Magli
$520.00
$229.99
56% Off
G.H. Bass & Co. Factory Outlet TAN Huey Short Duck Boot
Comparable Value
$130.00
$69.99
46% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Dallas Waterproof Boot
Comparable Value
$150.00
$89.99
40% Off
G.H. Bass & Co. Factory Outlet DESERT Conrad Chukka Boot
Comparable Value
$140.00
$69.99
50% Off
Cole Haan BRITISH TAN Conway Waterproof Chelsea Boots
Cole Haan
$300.00
$159.99
47% Off
Nautica VARSITY BLUE WASH Lanita Rain Boots
$60.00
$49.99
17% Off
Allen Edmonds BROWN Allen Edmonds Rafael Leather Boot
Allen Edmonds
$495.00
$219.99
56% Off
Allen Edmonds BEIGE Allen Edmonds Driggs Chuka Leather Loafer
Allen Edmonds
$295.00
$149.99
49% Off
Donald Pliner BLACK Donald Pliner Mark Leather Boot
Donald Pliner
$295.00
$89.99
69% Off
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