Skip to main content

$100+ receives free shipping

M-F, 6AM-6PM PST

Live Chat

Customer service

Call customer service

1-888-676-2660

M-F, 6AM-6PM PST

Live Chat

Live Chat

Shoes
Women's
Boots
Sneakers
Heels
Flats
Clogs & Mules
Sandals
View all...
Men's
Sneakers
Sandals
Loafers
Oxfords
Boat Shoes
Boots
View all...
Specialty Shops
Luxury Collections
1-Style Left
Athleisure
Running
Wide Shoes
Narrow Shoes
Work Shoes
Top Trending Brands
Crocs
Tommy Hilfiger
adidas
Dr. Martens
PUMA
Clothing
Women's
Dresses
Swimwear
Shirts & Tops
Jeans
Sweaters
View all...
Men's
T-Shirts
Swimwear
Jeans
Shorts
Sweaters
View all...
Specialty Shops
Career & Suiting
Athletic
Outdoor
Designer
Running
Athleisure
Plus Size
Yoga
Featured Brands
Bebe
J.Crew
Juicy Couture
London Times
Tommy Hilfiger
U.S. POLO ASSN.
Bags
All Bags
Handbags
Backpacks
Wallets & Accessories
Luggage
View all...
Top Styles
Cross Body
Totes
Shoulder Bags
Satchels
Belt Bags
Top Brands
COACH
Tommy Hilfiger
ZAC Zac Posen
Nine West
Frye
Specialty Shops
Designer
Career
Juniors'
Timeless Bags
Accessories
All Accessories
Sunglasses
Hats
Watches
Jewelry
Belts
Sunglass Styles
Aviators
Oval
Rectangular
Cat Eye
View all...
Top Brands
Oakley
Spy Optic
Under Armour
GUESS
Columbia
Featured Brands
Alex and Ani
GUESS
Michael Kors
Diff
Nixon
Women's
Shoes
Sandals
Sneakers
Heels
Boots
View all...
Clothing
Dresses
Swimsuits & Cover-Ups
Shirts & Tops
Activewear
View all...
Handbags
Eyewear
Watches
Jewelry
Accessories
Specialty Sizes
Plus Size
Petite
Wide Shoes
Narrow Shoes
Men's
Shoes
Sneakers
Oxfords
Sandals
Loafers
View all...
Clothing
T-Shirts
Jeans
Board Shorts
Activewear
View all...
Bags
Eyewear
Watches
Accessories
Fan Shop
Specialty Shops
Activewear
Athletic Shoes
Kids'
Boys
Shoes
Clothing
Accessories
View all...
Girls
Shoes
Clothing
Accessories
View all...
Shop by Age
Infant
Toddler
Little Kid
Big Kid
Clearance
Brands
Featured Brands
COACH
Brooks
Nine West
ASICS
UGG
SKECHERS
Cole Haan
Brand Index
#
A
B
C
D
E
F
G
H
I
J
K
L
M
N
O
P
Q
R
S
T
U
V
W
X
Y
Z
New Brands
Avec Les Filles
BCBGeneration
Bebe Sport
Chaser
Juicy Couture
Koolaburra By UGG
Tory Burch
Need Help?

Boots on Sale $50 or Less!

Shop Boot Deals

Skip to search results Skip to filters Skip to sort Skip to selected filters

Chukka Boots

26 items found

Sort By

Your Selections

Search Results

Born - Theo. Color Black. Low Stock. On sale for $86.65. MSRP $130.00.. 5.0 out of 5 stars

Low Stock

Born Theo

Born Theo

Brand Name: Born
Product Name: Theo
Gender: Men's
Color: Black
Price: $86.65MSRP: $130.00

See Kai Run - Casey (Infant/Toddler). Color Navy Suede. Low Stock. On sale for $45.88. MSRP $55.00.. 5.0 out of 5 stars

Low Stock

See Kai Run Casey (Infant/Toddler)

See Kai Run Casey (Infant/Toddler)

Brand Name: See Kai Run
Product Name: Casey (Infant/Toddler)
Color: Navy Suede
Price: $45.88MSRP: $55.00

Florsheim - Forge Plain Toe Chukka. Color Black. On sale for $112.45. MSRP $125.00.. 2.7 out of 5 stars

Florsheim Forge Plain Toe Chukka

Florsheim Forge Plain Toe Chukka

Brand Name: Florsheim
Product Name: Forge Plain Toe Chukka
Gender: Men's
Color: Black
Price: $112.45MSRP: $125.00

Bruno Magli - Taddeo. Color Taupe Suede. Low Stock. On sale for $168.75. MSRP $375.00..

Low Stock

Bruno Magli Taddeo

Bruno Magli Taddeo

Brand Name: Bruno Magli
Product Name: Taddeo
Gender: Men's
Color: Taupe Suede
Price: $168.75MSRP: $375.00

Cole Haan - Berkshire Lug Chukka Boot. Color Lava Suede/Dark. On sale for $211.37. MSRP $250.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Lava Suede/Dark
Price: $211.37MSRP: $250.00

Allen Edmonds - Graham Moccasins. Color Snuff Suede. Low Stock. On sale for $321.75. MSRP $495.00..

Low Stock

Allen Edmonds Graham Moccasins

Allen Edmonds Graham Moccasins

Brand Name: Allen Edmonds
Product Name: Graham Moccasins
Gender: Men's
Color: Snuff Suede
Price: $321.75MSRP: $495.00

Cole Haan - Berkshire Lug Chukka Boot. Color Bloodstone/Dark Natural Water Resistant. On sale for $216.00. MSRP $240.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Bloodstone/Dark Natural Water Resistant
Price: $216.00MSRP: $240.00

Stacy Adams - Martindale Chukka Boot. Color Bordeaux. On sale for $97.50. MSRP $130.00.. 4.0 out of 5 stars

Stacy Adams Martindale Chukka Boot

Stacy Adams Martindale Chukka Boot

Brand Name: Stacy Adams
Product Name: Martindale Chukka Boot
Gender: Men's
Color: Bordeaux
Price: $97.50MSRP: $130.00

Comfortiva - Holland. Color Black. Low Stock. On sale for $88.36. MSRP $129.95.. 3.8 out of 5 stars

Low Stock

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Black
Price: $88.36MSRP: $129.95

Polo Ralph Lauren - Talan Chukka Boot. Color Defender Green. On sale for $119.73. MSRP $138.00.. 4.2 out of 5 stars

Polo Ralph Lauren Talan Chukka Boot

Polo Ralph Lauren Talan Chukka Boot

Brand Name: Polo Ralph Lauren
Product Name: Talan Chukka Boot
Gender: Men's
Color: Defender Green
Price: $119.73MSRP: $138.00

Dr. Scholl's - Aurora. Color Charcoal Fabric. Low Stock. On sale for $46.00. MSRP $115.00.. 3.3 out of 5 stars

Low Stock

Dr. Scholl's Aurora

Dr. Scholl's Aurora

Brand Name: Dr. Scholl's
Product Name: Aurora
Gender: Women's
Color: Charcoal Fabric
Price: $46.00MSRP: $115.00

Dr. Scholl's - Aurora. Color Mocha Taupe Microfiber. On sale for $46.00. MSRP $115.00.. 3.3 out of 5 stars

Dr. Scholl's Aurora

Dr. Scholl's Aurora

Brand Name: Dr. Scholl's
Product Name: Aurora
Gender: Women's
Color: Mocha Taupe Microfiber
Price: $46.00MSRP: $115.00

ECCO - Grainer Chukka Boot. Color Camel. On sale for $134.77. MSRP $190.00.. 2.5 out of 5 stars

ECCO Grainer Chukka Boot

ECCO Grainer Chukka Boot

Brand Name: ECCO
Product Name: Grainer Chukka Boot
Gender: Men's
Color: Camel
Price: $134.77MSRP: $190.00

ECCO - London Plain Toe Chukka Boots. Color Cognac. On sale for $149.99. MSRP $225.00..

ECCO London Plain Toe Chukka Boots

ECCO London Plain Toe Chukka Boots

Brand Name: ECCO
Product Name: London Plain Toe Chukka Boots
Gender: Men's
Color: Cognac
Price: $149.99MSRP: $225.00

Born - Theo. Color Navy/Brown Distressed. Low Stock. On sale for $97.50. MSRP $130.00.. 5.0 out of 5 stars

Low Stock

Born Theo

Born Theo

Brand Name: Born
Product Name: Theo
Gender: Men's
Color: Navy/Brown Distressed
Price: $97.50MSRP: $130.00

See Kai Run - Casey (Infant/Toddler). Color Gray. Low Stock. On sale for $35.88. MSRP $52.00.. 5.0 out of 5 stars

Low Stock

See Kai Run Casey (Infant/Toddler)

See Kai Run Casey (Infant/Toddler)

Brand Name: See Kai Run
Product Name: Casey (Infant/Toddler)
Color: Gray
Price: $35.88MSRP: $52.00

La Canadienne - Alston. Color Taupe Suede. Low Stock. On sale for $212.50. MSRP $425.00..

Low Stock

La Canadienne Alston

La Canadienne Alston

Brand Name: La Canadienne
Product Name: Alston
Gender: Men's
Color: Taupe Suede
Price: $212.50MSRP: $425.00

Eastland 1955 Edition - Devin. Color Dark Brown. Low Stock. On sale for $81.00. MSRP $90.00..

Low Stock

Eastland 1955 Edition Devin

Eastland 1955 Edition Devin

Brand Name: Eastland 1955 Edition
Product Name: Devin
Gender: Men's
Color: Dark Brown
Price: $81.00MSRP: $90.00

Rockport - Berenger Plain Toe Chukka. Color Tan. Low Stock. On sale for $99.57. MSRP $119.95.. 3.5 out of 5 stars

Low Stock

Rockport Berenger Plain Toe Chukka

Rockport Berenger Plain Toe Chukka

Brand Name: Rockport
Product Name: Berenger Plain Toe Chukka
Gender: Men's
Color: Tan
Price: $99.57MSRP: $119.95

Johnston & Murphy Collection - Jenson Chukka. Color Brown Italian Calfskin. Low Stock. On sale for $203.55. MSRP $295.00.. 2.5 out of 5 stars

Low Stock

Johnston & Murphy Collection Jenson Chukka

Johnston & Murphy Collection Jenson Chukka

Brand Name: Johnston & Murphy Collection
Product Name: Jenson Chukka
Gender: Men's
Color: Brown Italian Calfskin
Price: $203.55MSRP: $295.00

Allen Edmonds - Graham Moccasins. Color Loden Suede. Low Stock. On sale for $350.00. MSRP $495.00..

Low Stock

Allen Edmonds Graham Moccasins

Allen Edmonds Graham Moccasins

Brand Name: Allen Edmonds
Product Name: Graham Moccasins
Gender: Men's
Color: Loden Suede
Price: $350.00MSRP: $495.00

Comfortiva - Holland. Color Light Grey. Low Stock. On sale for $64.97. MSRP $129.95.. 3.8 out of 5 stars

Low Stock

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Light Grey
Price: $64.97MSRP: $129.95

Martin Dingman - Ernest Kudu. Color Evergreen. Low Stock. On sale for $229.10. MSRP $395.00..

Low Stock

Martin Dingman Ernest Kudu

Martin Dingman Ernest Kudu

Brand Name: Martin Dingman
Product Name: Ernest Kudu
Gender: Men's
Color: Evergreen
Price: $229.10MSRP: $395.00

Tommy Hilfiger - Natash. Color Black. Low Stock. On sale for $81.75. MSRP $109.00..

Low Stock

Tommy Hilfiger Natash

Tommy Hilfiger Natash

Brand Name: Tommy Hilfiger
Product Name: Natash
Gender: Men's
Color: Black
Price: $81.75MSRP: $109.00

Tommy Hilfiger - Natash. Color Brown. Low Stock. On sale for $74.12. MSRP $109.00..

Low Stock

Tommy Hilfiger Natash

Tommy Hilfiger Natash

Brand Name: Tommy Hilfiger
Product Name: Natash
Gender: Men's
Color: Brown
Price: $74.12MSRP: $109.00

Dr. Scholl's - Aurora. Color Black Microfiber. Low Stock. On sale for $45.48. MSRP $115.00.. 3.3 out of 5 stars

Low Stock

Dr. Scholl's Aurora

Dr. Scholl's Aurora

Brand Name: Dr. Scholl's
Product Name: Aurora
Gender: Women's
Color: Black Microfiber
Price: $45.48MSRP: $115.00