Men's Boots & Chukkas

Displaying 404 items
Saks Fifth Avenue BLACK Rimini Eye Leather Chukka Boots
Saks Fifth Avenue
$200.00
$99.99
50% Off
Jo Ghost BROWN Almond Toe Leather Ankle Boots
Jo Ghost
$525.00
$174.99-$249.99
Up to 67% Off
Steve Madden COGNAC Yearn Leather Chelsea Boots
Steve Madden
$140.00
$69.99
50% Off
Cole Haan BLACK Nantucket Leather Boots
Cole Haan
$250.00
$139.99
44% Off
Cole Haan CHESTNUT Nathan Cap-Toe Leather Boots
Cole Haan
$250.00
$119.99
52% Off
COLE HAAN GRAND OS BLACK ZeroGrand Rugged Leather Chukka Boots
COLE HAAN GRAND OS
$300.00
$139.99
53% Off
Original Penguin TAN Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
Corthay BLACK Leather Chukka Boots
New!
Corthay
$1,995.00
$799.99
60% Off
G.H. Bass & Co. Factory Outlet TAUPE Trail 3.0 Hiking Boot
Comparable Value
$150.00
$69.99
53% Off
To Boot New York BLACK Brighton Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Karl Lagerfeld GREY Side-Zip Suede Chelsea Boots
Karl Lagerfeld
$360.00
$99.99
72% Off
Antonio Maurizi BROWN Antonio Maurizi Suede Boot
Antonio Maurizi
$525.00
$131.00
75% Off
Antonio Maurizi BLACK Antonio Maurizi Leather Boot
Antonio Maurizi
$535.00
$235.99
56% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$74.00
72% Off
Rush by Gordon Rush BROWN Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$275.00
$89.00
68% Off
The Frye Company BLACK Gordon Lace Up
The Frye Company
$278.00
$149.00
46% Off
Rush by Gordon Rush BLACK Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$260.00
$89.99
65% Off
Antonio Maurizi BROWN Antonio Maurizi Apron Leather Boot
Antonio Maurizi
$535.00
$259.99
51% Off
Rush by Gordon Rush BROWN Rush By Gordon Rush Leather Boot
Rush by Gordon Rush
$280.00
$119.99
57% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Louie Duck Boot
Comparable Value
$130.00
$69.99
46% Off
G.H. Bass & Co. Factory Outlet COGNAC Coleman Chukka Boot
Comparable Value
$120.00
$54.99
54% Off
G.H. Bass & Co. Factory Outlet COGNAC Lucas Lace-Up Boot
Comparable Value
$150.00
$79.99
47% Off
The Frye Company SLATE MULTI Scout Boot
The Frye Company
$278.00
$159.00
43% Off
G.H. Bass & Co. Factory Outlet COGNAC Barrington Lace-Up Boot
Comparable Value
$165.00
$89.99
45% Off
G.H. Bass & Co. Factory Outlet COGNAC Spencer Lace Up Boot
Comparable Value
$120.00
$69.99
42% Off
Aquatalia CHARCOAL Heath Suede Hiking Boots
Aquatalia
$595.00
$249.99
58% Off
The Frye Company WHEAT Sawyer Inside Zip
The Frye Company
$298.00
$199.00
33% Off
The Frye Company COGNAC Sawyer Inside Zip
The Frye Company
$298.00
$199.00
33% Off
The Frye Company FADED BROWN Paul Lace Up
The Frye Company
$328.00
$199.00
39% Off
John Varvatos Star U.S.A. CHARCOAL Star Leather Chelsea Boots
John Varvatos Star U.S.A.
$298.00
$149.99
50% Off
Arche 41|76 Zorak Boots
$595.00
$298.00
50% Off
G.H. Bass & Co. Factory Outlet CHOCOLATE Tyson Lace-Up Boot
Comparable Value
$160.00
$69.99
56% Off
G.H. Bass & Co. Factory Outlet TAUPE Radley Chukka Boot Ii
Comparable Value
$140.00
$64.99
54% Off
Arche 43|78 Whyou
$495.00
$248.00
50% Off
Bruno Magli ROASTED DARK BROWN Cardone Leather & Suede Boots
Bruno Magli
$520.00
$229.99
56% Off
Vince FLINT Aldous Suede Boots
Vince
$395.00
$189.99
52% Off
The Frye Company BLACK Ranger Chukka
The Frye Company
$139.00
$79.00
43% Off
The Frye Company BLACK Ryan Lug Trek
The Frye Company
$258.00
$149.00
42% Off
The Frye Company TAN Peak Work Boot
The Frye Company
$149.00
$99.00
34% Off
The Frye Company TAN Cody Lace Up
The Frye Company
$149.00
$99.00
34% Off
The Frye Company DARK BROWN Peak Work Boot
The Frye Company
$149.00
$99.00
34% Off
The Frye Company DARK BROWN Addison Lug Lace Up
The Frye Company
$458.00
$329.00
28% Off
The Frye Company DARK BROWN Ranger Chukka
The Frye Company
$139.00
$79.00
43% Off
The Frye Company DARK BROWN Cody Lace Up
The Frye Company
$149.00
$99.00
34% Off
G.H. Bass & Co. Factory Outlet SAND Radley Chukka Boot
Comparable Value
$140.00
$49.99
64% Off
Roberto Cavalli CAMEL Suede Chelsea Boots
Roberto Cavalli
$675.00
$249.99
63% Off
Buscemi BLACK Lotta Canvas Hiking Boots
Buscemi
$795.00
$369.99
53% Off
Cole Haan BRITISH TAN Conway Waterproof Chelsea Boots
Cole Haan
$300.00
$159.99
47% Off
G.H. Bass & Co. Factory Outlet DARK BROWN Hendrick Chelsea Boot
Comparable Value
$150.00
$129.99
13% Off
G.H. Bass & Co. Factory Outlet DARK BROWN Scout Runner Mid Boot
Comparable Value
$160.00
$139.99
13% Off
The Frye Company BROWN Peyton Chelsea
The Frye Company
$278.00
$199.00
28% Off
The Frye Company SLATE Peyton Lace Up
The Frye Company
$298.00
$199.00
33% Off
Nautica BROWN STONE Lace Up Winter Boots
New!
$70.00
$52.50
25% Off
Nautica GREY SHADOW Nautica Competiton Boots
New!
$70.00
$52.50
25% Off
The Frye Company BLACK Graham Brogue Chukka
The Frye Company
$398.00
$249.00
37% Off
Aquatalia BURGUNDY Waterproof Leather Boots
Aquatalia
$595.00
$249.99
58% Off
The Frye Company DARK GREY Field Lace Up
The Frye Company
$298.00
$179.00
40% Off
Aquatalia BROWN Adrian Leather Chelsea Boots
Aquatalia
$450.00
$219.99
51% Off
Roberto Cavalli BLACK Wingtip Pebbled-Leather Combat Boots
Roberto Cavalli
$665.00
$269.99
59% Off
Ben Sherman DARK BROWN Gabe Leather Chukka Boots
Ben Sherman
$130.00
$69.99
46% Off
The Frye Company BLACK Korver Utility Boot
The Frye Company
$328.00
$179.00
45% Off
The Frye Company FADED BROWN Grady Chelsea
New!
The Frye Company
$378.00
$199.00
47% Off
The Frye Company WHEAT Johnny Chelsea
The Frye Company
$278.00
$169.00
39% Off
The Frye Company BLACK Johnny Chelsea
The Frye Company
$278.00
$169.00
39% Off
The Frye Company BLACK Johnny Combat
The Frye Company
$298.00
$189.00
37% Off
To Boot New York SIENNA Brighton Suede Ankle Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
To Boot New York BROWN Rosemont Leather Boots
To Boot New York
$398.00
$199.99
50% Off
The Frye Company WHEAT Duke Roper
The Frye Company
$398.00
$299.00
25% Off
Ben Sherman BLACK Brent Plain Toe Leather Ankle Boots
Ben Sherman
$145.00
$79.99
45% Off
Karl Lagerfeld Paris BLACK Leather Chelsea Boots
Karl Lagerfeld Paris
$375.00
$119.99
68% 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
Karl Lagerfeld Paris BLACK Faux Fur-Lined Leather Boots
Karl Lagerfeld Paris
$395.00
$129.99
67% Off
Original Penguin SHIITAKE Monty Leather Chukka Boots
Original Penguin
$185.00
$99.99
46% Off
Karl Lagerfeld Paris BLACK Buckled Leather Ankle Boots
Karl Lagerfeld Paris
$375.00-$450.00
$129.99
Up to 71% Off
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