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Brand
Allen-Edmonds
Allen-Edmonds
Ariat
Ariat
Bed Stu
Bed Stu
Belvedere
Belvedere
Born
Born
COACH
COACH
Cole Haan
Cole Haan
Danner
Danner
Dr. Martens
Dr. Martens
Eastland
Eastland
Flag LTD.
Flag LTD.
Frye
Frye
G.H. Bass
G.H. Bass
HEYDUDE
HEYDUDE
Johnston & Murphy
Johnston & Murphy
Josef Seibel
Josef Seibel
Steve Madden
Steve Madden
Ted Baker London
Ted Baker London
Timberland
Timberland
Twisted X
Twisted X
UGG
UGG
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68 Items
HEYDUDE
Men's Wally Sox Washable Chukkas
59.99
Extended Sizes
Rated 4.61 out of 5 stars
Rated 4.61 out of 5 stars
Rated 4.61 out of 5 stars
Rated 4.61 out of 5 stars
Rated 4.61 out of 5 stars
(2223)
Johnston & Murphy
Boys' McGuffey Leather Lace-Up Chukka Boots (Youth)
65.00
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
(30)
Johnston & Murphy
Men's Upton Chukka Boots
169.00
Extended Sizes
Rated 4.29 out of 5 stars
Rated 4.29 out of 5 stars
Rated 4.29 out of 5 stars
Rated 4.29 out of 5 stars
Rated 4.29 out of 5 stars
(17)
Twisted X
Women's Original Chukka Driving Mocs
124.99
Extended Sizes
Rated 4.64 out of 5 stars
Rated 4.64 out of 5 stars
Rated 4.64 out of 5 stars
Rated 4.64 out of 5 stars
Rated 4.64 out of 5 stars
(11)
Johnston & Murphy
Boys' McGuffey Oiled Nubuck Leather Chukka Boots (Youth)
65.00
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
Rated 4.73 out of 5 stars
(30)
Steve Madden
Men's Harken Chukka Boots
89.99
Extended Sizes
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
(60)
Frye
Men's Astor Leather Chukka Boots
228.00
Extended Sizes
HEYDUDE
Men's Wally Washable Canvas Chukkas
64.99
Extended Sizes
Rated 4.23 out of 5 stars
Rated 4.23 out of 5 stars
Rated 4.23 out of 5 stars
Rated 4.23 out of 5 stars
Rated 4.23 out of 5 stars
(131)
Josef Seibel
Men's Earl 04 Leather Lace-Up Chukka Boots
170.00
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(5)
Born
Men's Harrison Leather Chukka Boots
135.00
Extended Sizes
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
(32)
Twisted X
Men's Waterproof Chukka Driving Moccasins
149.99
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(3)
Twisted X
Women's Tooled Leather Chukka Driving Mocs
124.99
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(3)
Twisted X
Men's Leather Lace-Up Chukka Driving Moccasins
129.99
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(3)
Johnston & Murphy
Men's Upton Leather Lace-Up Chukka Boots
169.00
Internet Exclusive
Extended Sizes
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
(2)
UGG
Women's Neumel Suede Lace-Up Chukka Boots
Save on Select Items
Orig.
140.00
Now
70.00
-
140.00
Extended Sizes
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(9511)
Steve Madden
Boys' T-Harkeen Leather Chukka Boots (Infant)
64.99
Danner
Women's Inquire Chukka Waterproof Cold Weather Suede Hiking Boots
150.00
Extended Sizes
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
(4)
Twisted X
Men's Driving Leather Chukka Moccasins
129.99
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(6)
HEYDUDE
Men's Wally Linen Washable Chukkas
64.99
Extended Sizes
Rated 4.32 out of 5 stars
Rated 4.32 out of 5 stars
Rated 4.32 out of 5 stars
Rated 4.32 out of 5 stars
Rated 4.32 out of 5 stars
(593)
Timberland
Men's Maple Grove Chukka Boots
125.00
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
(59)
Twisted X
Women's Embroidered Chukka Driving Mocs
124.99
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(7)
Ariat
Men's Lookout Chukka Boots
149.99
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
(64)
Twisted X
Women's Tooled Chukka Driving Mocs
124.99
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(8)
Steve Madden
Men's Hestonn Chukka Boots
89.99
Extended Sizes
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(39)
Timberland
Men's Maplegrove Chukka Boots
125.00
Extended Sizes
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
Rated 4.46 out of 5 stars
(59)
UGG
Men's Neumel Classic Fur Lined Suede Lace-Up Chukka Boots
Save on Select Items
Orig.
140.00
Now
70.00
-
140.00
Extended Sizes
Rated 4.84 out of 5 stars
Rated 4.84 out of 5 stars
Rated 4.84 out of 5 stars
Rated 4.84 out of 5 stars
Rated 4.84 out of 5 stars
(6158)
Johnston & Murphy
Boys' McGuffey Leather Chukka Boots (Infant)
65.00
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(7)
Dr. Martens
Men's Bonny Chukka Boots
110.00
Extended Sizes
Rated 4.93 out of 5 stars
Rated 4.93 out of 5 stars
Rated 4.93 out of 5 stars
Rated 4.93 out of 5 stars
Rated 4.93 out of 5 stars
(14)
Belvedere
Men's Alvaro Hand Painted Multi Color Ostrich Chukka Boots
620.00
Internet Exclusive
Extended Sizes
Steve Madden
Boys' T-Harkeen Leather Chukka Boots (Toddler)
64.99
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
(5)
UGG
Men's Burleigh Waterproof Cold Weather Chukka Boots
160.00
Extended Sizes
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
(8)
Johnston & Murphy
Boys' McGuffey Leather Chukka Boots (Toddler)
65.00
Rated 4.92 out of 5 stars
Rated 4.92 out of 5 stars
Rated 4.92 out of 5 stars
Rated 4.92 out of 5 stars
Rated 4.92 out of 5 stars
(13)
Twisted X
Men's Driving CellStretch Chukka Moccasins
149.99
Extended Sizes
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
(1)
Twisted X
Men's Work Steel Toe Leather Chukka Driving Moccasins
144.99
Extended Sizes
Timberland
Men's Redwood Falls Waterproof Leather Chukka Boots
130.00
-
135.00
Extended Sizes
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
(91)
Dr. Martens
Men's Crewson Chukka Boots
150.00
Internet Exclusive
Extended Sizes
Ariat
Men's Lookout Chukka Boots
149.99
Internet Exclusive
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
Rated 4.08 out of 5 stars
(64)
Twisted X
Women's Turquoise Embroidered Chukka Driving Mocs
124.99
Extended Sizes
Twisted X
Men's Slip-On Chukka Leather Driving Moccasin Boot
134.99
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(2)
G.H. Bass
Women's Blair Suede Chukka Booties
155.00
Extended Sizes
Rated 3 out of 5 stars
Rated 3 out of 5 stars
Rated 3 out of 5 stars
Rated 3 out of 5 stars
Rated 3 out of 5 stars
(2)
Frye
Men's Astor Chukka Boots
228.00
Twisted X
Men's Work Steel Toe Chukka Driving Moccasins
139.99
Internet Exclusive
Extended Sizes
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
Rated 2 out of 5 stars
(1)
Allen-Edmonds
Men's Harris Chukka Leather Boots
395.00
Internet Exclusive
Extended Sizes
Frye
Men's Astor Leather Lace-Up Chukka Boots
228.00
Internet Exclusive
Extended Sizes
Bed Stu
Men's Clyde Leather Chukka Boots
275.00
Internet Exclusive
Extended Sizes
Twisted X
Men's Chukka Driving Moccasins
149.99
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(1)
Twisted X
Men's Driving Woven Leather Chukka Moccasins
135.99
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(1)
Allen-Edmonds
Men's Harris Chukka Suede Boots
395.00
Internet Exclusive
Extended Sizes
Steve Madden
Men's Manoa Nubuck Lace-Up Casual Chukkas
140.00
Internet Exclusive
Extended Sizes
Timberland
Men's Ashwood Park Chukkas
100.00
Internet Exclusive
Extended Sizes
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
(24)
Frye
Men's Astor Suede Chukka Boots
228.00
Internet Exclusive
Extended Sizes
Danner
Women's Inquire Chukka Waterproof Leather Hiking Boots
150.00
Extended Sizes
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
(4)
Twisted X
Women's Printed Chukka Driving Moccasins
124.99
Internet Exclusive
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(2)
Twisted X
Women's Sunflower Chukka Driving Moccasins
124.99
Extended Sizes
Rated 1 out of 5 stars
Rated 1 out of 5 stars
Rated 1 out of 5 stars
Rated 1 out of 5 stars
Rated 1 out of 5 stars
(1)
Ted Baker London
Men's Clare Suede Chukkas
195.00
Internet Exclusive
Extended Sizes
Twisted X
Women's Embroidered Chukka Driving Mocs
124.99
Internet Exclusive
Extended Sizes
Danner
Women's Forest Chukka Nubuck Leather Shoes
160.00
Internet Exclusive
Extended Sizes
Eastland
Men's Jack Chukka Boots
109.99
-
124.99
Internet Exclusive
Eastland
Men's Seneca Leather Chukka Boots
119.99
Internet Exclusive
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(2)
Twisted X
Women's Tooled Turquoise Stud Chukka Driving Mocs
149.99
Extended Sizes
Rated 4 out of 5 stars
Rated 4 out of 5 stars
Rated 4 out of 5 stars
Rated 4 out of 5 stars
Rated 4 out of 5 stars
(5)
Johnston & Murphy
Men's XC Flex Raleigh Chukka Boots
Permanently Reduced
Orig.
175.00
Now
119.99
Cole Haan
Men's Hawthorne Chukka Boots
Permanently Reduced
Orig.
160.00
Now
107.20
Extended Sizes
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
(9)
COACH
Men's Micro Signature Jacquard Chukka Boots
Permanently Reduced
Orig.
295.00
Now
99.99
Internet Exclusive
Extended Sizes
Only size 8M available
COACH
Men's Signature Lug Sole Chukka Boots
Permanently Reduced
Orig.
295.00
Now
99.99
-
147.50
Extended Sizes
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
Rated 4.88 out of 5 stars
(8)
Cole Haan
Men's ØriginalGrand Leather Chukka Boots
Permanently Reduced
Orig.
180.00
Now
79.99
Extended Sizes
Only size 8.5M available
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(293)
Cole Haan
Men's 2.ZERØGRAND Leather Lace-Up Chukka Boots
Permanently Reduced
Orig.
180.00
Now
120.60
Extended Sizes
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
(331)
Flag LTD.
Men's Russell Suede Chukka Boots
Permanently Reduced
Orig.
130.00
Now
49.99
Dillard's Exclusive
Extended Sizes
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
Rated 5 out of 5 stars
(2)
Flag LTD.
Men's Russell Chukka Boots
Permanently Reduced
Orig.
130.00
Now
49.99
Dillard's Exclusive
Extended Sizes
Only size 10M available
68 Items
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