Men's Boots & Chukkas

Displaying 339 items
The Frye Company SLATE Peyton Chelsea
New!
The Frye Company
$278.00
$199.00
28% Off
The Frye Company BLACK Peyton Lace Up
New!
The Frye Company
$298.00
$199.00
33% Off
Nautica BROWN Madryn Boots
$70.00
$52.50
25% Off
The Frye Company DARK BROWN Field Lace Up
New!
The Frye Company
$298.00
$179.00
40% Off
Nautica TRUE BLACK Madryn Boots
$70.00
$52.50
25% Off
The Frye Company BLACK Gordon Lace Up
New!
The Frye Company
$278.00
$149.00
46% Off
The Frye Company BLACK Phillip Chukka
New!
The Frye Company
$298.00
$149.00
50% Off
The Frye Company BLACK Bruce Pull On
New!
The Frye Company
$458.00
$299.00
35% Off
The Frye Company ASH Emory Chukka
The Frye Company
$268.00
$169.00
37% Off
Arche 44|80 Trotteurs Whyou
$495.00
$248.00
50% Off
Arche 43|78 Boots Zorak
$595.00
$298.00
50% Off
Zadig & Voltaire COGNAC Romare Boots
New!
$398.00
$278.60
30% Off
The Frye Company WHEAT Jackson Chukka
The Frye Company
$129.00
$99.00
23% Off
The Frye Company CHOCOLATE Tyler Chelsea
The Frye Company
$328.00
$199.00
39% Off
The Frye Company BURGUNDY Fisher Chelsea
The Frye Company
$428.00
$239.00
44% Off
The Frye Company DARK ASH Bowery Chukka
The Frye Company
$328.00
$229.00
30% Off
The Frye Company DARK ASH Bryant Lace Up
The Frye Company
$328.00
$199.00
39% Off
The Frye Company BLACK Tanker Lace Up
New!
The Frye Company
$428.00
$259.00
39% Off
The Frye Company BLACK Bryant Lace Up
The Frye Company
$328.00
$199.00
39% Off
The Frye Company WHITE Western Chelsea
New!
The Frye Company
$378.00
$249.00
34% Off
The Frye Company BLACK James Chelsea
New!
The Frye Company
$298.00
$199.00
33% Off
The Frye Company BLACK Graham Brogue Chukka
New!
The Frye Company
$398.00
$249.00
37% Off
The Frye Company BLACK Western Chelsea
New!
The Frye Company
$378.00
$249.00
34% Off
Zadig & Voltaire BLACK Joe Boots
New!
$468.00
$327.60
30% Off
The Frye Company COGNAC Sawyer Chelsea
New!
The Frye Company
$278.00
$199.00
28% Off
The Frye Company COGNAC Tanker Lace Up
New!
The Frye Company
$428.00
$259.00
39% Off
The Frye Company COGNAC Essex Chelsea Shearling
The Frye Company
$298.00
$109.00
63% Off
The Frye Company RED Bruce Pull On
New!
The Frye Company
$458.00
$299.00
35% Off
The Frye Company DARK BROWN Jackson Chelsea
The Frye Company
$139.00
$99.00
29% Off
The Frye Company SMOKE Jackson Chukka
The Frye Company
$129.00
$99.00
23% Off
Karl Lagerfeld Paris BLACK Buckled Leather Ankle Boots
Karl Lagerfeld Paris
$375.00-$450.00
$129.99
Up to 71% Off
Cole Haan BLACK Nantucket Leather Boots
Cole Haan
$250.00
$139.99
44% Off
COLE HAAN GRAND OS BLACK ZeroGrand Rugged Leather Chukka Boots
COLE HAAN GRAND OS
$300.00
$139.99
53% Off
To Boot New York BLACK Brighton Chelsea Boots
To Boot New York
$425.00
$199.99
53% Off
Roberto Cavalli BLACK Side Buckle Leather Boots
Roberto Cavalli
$720.00
$249.99
65% Off
Steve Madden BLACK Irving Chelsea Boots
Steve Madden
$120.00
$79.99
33% Off
Steve Madden BLACK Leather Buckle Boots
Steve Madden
$140.00
$99.99
29% Off
Johnston & Murphy BLACK Bryson Leather Wingtip Boots
New!
Johnston & Murphy
$298.00
$149.99
50% Off
Buscemi BLACK Textured Leather Site Boots
New!
Buscemi
$1,250.00
$549.99
56% Off
Buscemi BLACK Lotta Canvas Hiking Boots
New!
Buscemi
$795.00
$369.99
53% Off
Bruno Magli BLACK Leather Chelsea Boots
Bruno Magli
$460.00-$480.00
$219.99
Up to 54% Off
Costume National GREY Stretch Knit Sock Boots
Costume National
$475.00
$139.97
71% Off
Magnanni GREY Leather Chukka Boots
Magnanni
$495.00
$249.99
49% Off
Johnston & Murphy GREY Carriker Chelsea Boots
New!
Johnston & Murphy
$140.00
$69.99
50% Off
Paul Stuart GREY Lace-Up Suede Hiker Boots
Paul Stuart
$695.00
$244.97
65% Off
Mezlan BROWN Brogue Leather Boots
Mezlan
$450.00
$229.99
49% Off
Nettleton BROWN Suede Chelsea Boots
Nettleton
$595.00
$199.99
66% Off
Jo Ghost BROWN Lizard-Embossed Leather Boots
New!
Jo Ghost
$525.00
$249.99
52% Off
Massimo Matteo BROWN Buckled Leather Chelsea Boots
Massimo Matteo
$295.00-$325.00
$104.97-$149.99
Up to 68% Off
Kenneth Cole REACTION BROWN Round-Toe Leather Ankle Boots
Kenneth Cole REACTION