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 & Under

Shop Boots Deals

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

Medium Size Chukka Boots

21 items found

Sort By

Your Selections

Search Results

Koolaburra by UGG - Advay. Color Black. On sale for $49.97. MSRP $84.99. 41% off. 3.6 out of 5 stars

Koolaburra by UGG Advay

Koolaburra by UGG Advay

Brand Name: Koolaburra by UGG
Product Name: Advay
Gender: Women's
Color: Black
Price: $49.97MSRP: $84.99

Dolce Vita - Ronnie. Color Camel Suede. On sale for $43.99. MSRP $220.00. 80% off. 3.5 out of 5 stars

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Camel Suede
Price: $43.99MSRP: $220.00

Comfortiva - Holland. Color Olive. On sale for $38.99. MSRP $129.95. 70% off. 3.8 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Olive
Price: $38.99MSRP: $129.95

Dolce Vita - Ronnie. Color Ivory Leather. Low Stock. On sale for $44.00. MSRP $220.00. 80% off. 3.5 out of 5 stars

Low Stock

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Ivory Leather
Price: $44.00MSRP: $220.00

Hey Dude - Wendy Wooly Twill Fold Boot. Color Cream Multi. Low Stock. On sale for $38.49. MSRP $69.99. 45% off. 4.5 out of 5 stars

Low Stock

Hey Dude Wendy Wooly Twill Fold Boot

Hey Dude Wendy Wooly Twill Fold Boot

Brand Name: Hey Dude
Product Name: Wendy Wooly Twill Fold Boot
Gender: Women's
Color: Cream Multi
Price: $38.49MSRP: $69.99

Koolaburra by UGG - Advay. Color Dune. On sale for $67.72. MSRP $84.99. 20% off. 3.6 out of 5 stars

Koolaburra by UGG Advay

Koolaburra by UGG Advay

Brand Name: Koolaburra by UGG
Product Name: Advay
Gender: Women's
Color: Dune
Price: $67.72MSRP: $84.99

Hey Dude - Reyes Boot Wool. Color Light Grey. Low Stock. On sale for $77.01. MSRP $89.99. 14% off. 4.2 out of 5 stars

Low Stock

Hey Dude Reyes Boot Wool

Hey Dude Reyes Boot Wool

Brand Name: Hey Dude
Product Name: Reyes Boot Wool
Gender: Women's
Color: Light Grey
Price: $77.01MSRP: $89.99

Twisted X - WDM0071. Color Bomber/Mahogany. Low Stock. On sale for $56.23. MSRP $124.95. 55% off. 3.6 out of 5 stars

Low Stock

Twisted X WDM0071

Twisted X WDM0071

Brand Name: Twisted X
Product Name: WDM0071
Gender: Women's
Color: Bomber/Mahogany
Price: $56.23MSRP: $124.95

Hey Dude - Britt. Color Coffee Dye. Low Stock. On sale for $58.45. MSRP $64.95. 10% off. 4.7 out of 5 stars

Low Stock

Hey Dude Britt

Hey Dude Britt

Brand Name: Hey Dude
Product Name: Britt
Gender: Women's
Color: Coffee Dye
Price: $58.45MSRP: $64.95

Dolce Vita - Ronnie. Color Black Leather. Low Stock. On sale for $98.96. MSRP $220.00. 55% off. 3.5 out of 5 stars

Low Stock

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Black Leather
Price: $98.96MSRP: $220.00

Hey Dude - Wendy Wooly Twill Fold Boot. Color Brown. Low Stock. On sale for $38.49. MSRP $69.99. 45% off. 4.5 out of 5 stars

Low Stock

Hey Dude Wendy Wooly Twill Fold Boot

Hey Dude Wendy Wooly Twill Fold Boot

Brand Name: Hey Dude
Product Name: Wendy Wooly Twill Fold Boot
Gender: Women's
Color: Brown
Price: $38.49MSRP: $69.99

Hey Dude - Wendy Wooly Twill Fold Boot. Color Black. Low Stock. On sale for $31.50. MSRP $69.99. 55% off. 4.5 out of 5 stars

Low Stock

Hey Dude Wendy Wooly Twill Fold Boot

Hey Dude Wendy Wooly Twill Fold Boot

Brand Name: Hey Dude
Product Name: Wendy Wooly Twill Fold Boot
Gender: Women's
Color: Black
Price: $31.50MSRP: $69.99

Hey Dude - Britt. Color Boho Chevron. Low Stock. On sale for $20.98. MSRP $69.95. 70% off. 4.6 out of 5 stars

Low Stock

Hey Dude Britt

Hey Dude Britt

Brand Name: Hey Dude
Product Name: Britt
Gender: Women's
Color: Boho Chevron
Price: $20.98MSRP: $69.95

Josef Seibel - Conny 56. Color Bordeaux. Low Stock. On sale for $70.00. MSRP $175.00. 60% off. 4.3 out of 5 stars

Low Stock

Josef Seibel Conny 56

Josef Seibel Conny 56

Brand Name: Josef Seibel
Product Name: Conny 56
Gender: Women's
Color: Bordeaux
Price: $70.00MSRP: $175.00

Josef Seibel - Conny 56. Color Moos. Low Stock. On sale for $113.75. MSRP $175.00. 35% off. 4.3 out of 5 stars

Low Stock

Josef Seibel Conny 56

Josef Seibel Conny 56

Brand Name: Josef Seibel
Product Name: Conny 56
Gender: Women's
Color: Moos
Price: $113.75MSRP: $175.00

Easy Street - Arctic. Color Brown/Caramel. Low Stock. On sale for $35.99. MSRP $79.99. 55% off.

Low Stock

Easy Street Arctic

Easy Street Arctic

Brand Name: Easy Street
Product Name: Arctic
Gender: Women's
Color: Brown/Caramel
Price: $35.99MSRP: $79.99

Dr. Scholl's - Aurora. Color Charcoal Fabric. Low Stock. On sale for $82.50. MSRP $115.00. 28% off. 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: $82.50MSRP: $115.00

Dr. Martens - Corran 3i Boot. Color Black Atlas. Low Stock. On sale for $171.00. MSRP $190.00. 10% off. 4.0 out of 5 stars

Low Stock

Dr. Martens Corran 3i Boot

Dr. Martens Corran 3i Boot

Brand Name: Dr. Martens
Product Name: Corran 3i Boot
Gender: Women's
Color: Black Atlas
Price: $171.00MSRP: $190.00

Moral Code - Faye Chukka Boot. Color Cognac. Low Stock. On sale for $111.00. MSRP $185.00. 40% off.

Low Stock

Moral Code Faye Chukka Boot

Moral Code Faye Chukka Boot

Brand Name: Moral Code
Product Name: Faye Chukka Boot
Gender: Women's
Color: Cognac
Price: $111.00MSRP: $185.00

SAS - Kich. Color Almond. Low Stock. On sale for $58.74. MSRP $234.95. 75% off. 4.4 out of 5 stars

Low Stock

SAS Kich

SAS Kich

Brand Name: SAS
Product Name: Kich
Gender: Women's
Color: Almond
Price: $58.74MSRP: $234.95

Hey Dude - Wendy Peak Suede Fold Boot. Color Black. Low Stock. $89.99. 4.1 out of 5 stars

Low Stock

Hey Dude Wendy Peak Suede Fold Boot

Hey Dude Wendy Peak Suede Fold Boot

Brand Name: Hey Dude
Product Name: Wendy Peak Suede Fold Boot
Gender: Women's
Color: Black
Price: $89.99