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

Chukka Boots

46 items found

Filters

Search Results

Birkenstock - Uppsala Mid Lace-Up Shearling - Suede. Color Dark Tea. On sale for $90.00. MSRP $180.00. 50% off. 4.1 out of 5 stars

Birkenstock Uppsala Mid Lace-Up Shearling - Suede

Birkenstock Uppsala Mid Lace-Up Shearling - Suede

Brand Name: Birkenstock
Product Name: Uppsala Mid Lace-Up Shearling - Suede
Gender: Women's
Color: Dark Tea
Price: $90MSRP: $180

Clarks - Relaxlite Moc. Color Cola Suede. Low Stock. On sale for $62.09. MSRP $110.00. 44% off.

Low Stock

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Cola Suede
Price: $62.09MSRP: $110

Dolce Vita - Ronnie. Color Camel Suede. Low Stock. On sale for $65.98. MSRP $220.00. 70% 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: Camel Suede
Price: $65.98MSRP: $220

Clarks - Relaxlite Moc. Color Black Suede. Low Stock. On sale for $55.00. MSRP $110.00. 50% off.

Low Stock

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Black Suede
Price: $55MSRP: $110

Johnston & Murphy - Brody Chukka. Color Snuff Suede. Low Stock. On sale for $49.50. MSRP $165.00. 70% off.

Low Stock

Johnston & Murphy Brody Chukka

Johnston & Murphy Brody Chukka

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Snuff Suede
Price: $49.50MSRP: $165

Kenneth Cole - Vesto. Color Black. On sale for $66.84. MSRP $118.95. 44% off.

Kenneth Cole Vesto

Kenneth Cole Vesto

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Black
Price: $66.84MSRP: $118.95

Kenneth Cole - Vesto. Color Medium Brown. On sale for $77.81. MSRP $118.95. 35% off.

Kenneth Cole Vesto

Kenneth Cole Vesto

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Medium Brown
Price: $77.81MSRP: $118.95

Birkenstock - Uppsala Mid Lace-Up Shearling - Suede. Color Black. On sale for $126.00. MSRP $180.00. 30% off. 4.1 out of 5 stars

Birkenstock Uppsala Mid Lace-Up Shearling - Suede

Birkenstock Uppsala Mid Lace-Up Shearling - Suede

Brand Name: Birkenstock
Product Name: Uppsala Mid Lace-Up Shearling - Suede
Gender: Women's
Color: Black
Price: $126MSRP: $180

Born - Analia. Color Green (Olive). On sale for $112.00. MSRP $140.00. 20% off. 3.2 out of 5 stars

Born Analia

Born Analia

Brand Name: Born
Product Name: Analia
Gender: Women's
Color: Green (Olive)
Price: $112MSRP: $140

Born - Analia. Color Burgundy (Brick). On sale for $98.00. MSRP $140.00. 30% off. 3.2 out of 5 stars

Born Analia

Born Analia

Brand Name: Born
Product Name: Analia
Gender: Women's
Color: Burgundy (Brick)
Price: $98MSRP: $140

Steve Madden - Daviston. Color Black. On sale for $124.05. MSRP $165.00. 25% off.

Steve Madden Daviston

Steve Madden Daviston

Brand Name: Steve Madden
Product Name: Daviston
Gender: Men's
Color: Black
Price: $124.05MSRP: $165

Frye - Paul Chukka. Color Brown. Low Stock. On sale for $131.60. MSRP $188.00. 30% off. 4.0 out of 5 stars

Low Stock

Frye Paul Chukka

Frye Paul Chukka

Brand Name: Frye
Product Name: Paul Chukka
Gender: Men's
Color: Brown
Price: $131.60MSRP: $188

Steve Madden - Daviston. Color Brown. On sale for $125.94. MSRP $165.00. 24% off.

Steve Madden Daviston

Steve Madden Daviston

Brand Name: Steve Madden
Product Name: Daviston
Gender: Men's
Color: Brown
Price: $125.94MSRP: $165

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Black/Black. On sale for $140.00. MSRP $200.00. 30% off. 2.7 out of 5 stars

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Black/Black
Price: $140MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Scotch/Alabaster. Low Stock. $200.00. 2.7 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Scotch/Alabaster
Price: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. Low Stock. On sale for $113.00. MSRP $200.00. 44% off. 2.7 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Woodbury/Dark Roast
Price: $113MSRP: $200

KEEN - KS Moc Chukka. Color Bison/Bison. Low Stock. On sale for $125.95. MSRP $139.95. 10% off.

Low Stock

KEEN KS Moc Chukka

KEEN KS Moc Chukka

Brand Name: KEEN
Product Name: KS Moc Chukka
Gender: Men's
Color: Bison/Bison
Price: $125.95MSRP: $139.95

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Chocolate Raisin/Natural/Dark Sequoia Wp. Low Stock. On sale for $180.00. MSRP $200.00. 10% off. 2.7 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Chocolate Raisin/Natural/Dark Sequoia Wp
Price: $180MSRP: $200

Comfortiva - Holland. Color Light Grey. On sale for $58.47. MSRP $129.95. 55% off. 3.9 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Light Grey
Price: $58.47MSRP: $129.95

Comfortiva - Holland. Color Olive. On sale for $90.96. MSRP $129.95. 30% off. 3.9 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Olive
Price: $90.96MSRP: $129.95

Comfortiva - Holland. Color Black. On sale for $51.98. MSRP $129.95. 60% off. 3.9 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Black
Price: $51.98MSRP: $129.95

Born - Erik. Color Brown (Castano). On sale for $120.00. MSRP $160.00. 25% off.

Born Erik

Born Erik

Brand Name: Born
Product Name: Erik
Gender: Men's
Color: Brown (Castano)
Price: $120MSRP: $160

Stacy Adams - Eastmont Elastic Lace Boots. Color Cognac. Low Stock. On sale for $56.00. MSRP $140.00. 60% off. 4.0 out of 5 stars

Low Stock

Stacy Adams Eastmont Elastic Lace Boots

Stacy Adams Eastmont Elastic Lace Boots

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: Cognac
Price: $56MSRP: $140

Marc Fisher LTD - Percy. Color Medium Brown Suede. Low Stock. On sale for $101.69. MSRP $112.99. 10% off.

Low Stock

Marc Fisher LTD Percy

Marc Fisher LTD Percy

Brand Name: Marc Fisher LTD
Product Name: Percy
Gender: Women's
Color: Medium Brown Suede
Price: $101.69MSRP: $112.99

Marc Fisher LTD - Percy. Color Dark Brown Leather. $112.99.

Marc Fisher LTD Percy

Marc Fisher LTD Percy

Brand Name: Marc Fisher LTD
Product Name: Percy
Gender: Women's
Color: Dark Brown Leather
Price: $112.99

Sperry - Tour Mid Moc. Color Tan. Low Stock. On sale for $126.00. MSRP $140.00. 10% off.

Low Stock

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Tan
Price: $126MSRP: $140

Johnston & Murphy - Brody Chukka. Color Brown Hand-Stained Calfskin. Low Stock. On sale for $82.50. MSRP $165.00. 50% off.

Low Stock

Johnston & Murphy Brody Chukka

Johnston & Murphy Brody Chukka

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Brown Hand-Stained Calfskin
Price: $82.50MSRP: $165

Clarks - Wallaston Boot. Color Cola Suede. On sale for $97.50. MSRP $120.00. 19% off. 4.0 out of 5 stars

Clarks Wallaston Boot

Clarks Wallaston Boot

Brand Name: Clarks
Product Name: Wallaston Boot
Gender: Men's
Color: Cola Suede
Price: $97.50MSRP: $120

Clarks - Steadwell Mid. Color Black Leather. On sale for $72.50. MSRP $110.00. 34% off.

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $72.50MSRP: $110

Sperry - Tour Mid Moc. Color Dark Brown. On sale for $112.00. MSRP $140.00. 20% off.

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Dark Brown
Price: $112MSRP: $140

Steve Madden - Palta. Color Sand. Low Stock. On sale for $65.00. MSRP $130.00. 50% off.

Low Stock

Steve Madden Palta

Steve Madden Palta

Brand Name: Steve Madden
Product Name: Palta
Gender: Men's
Color: Sand
Price: $65MSRP: $130

Sperry - Newton Boots. Color Taupe. On sale for $148.50. MSRP $165.00. 10% off. 5.0 out of 5 stars

Sperry Newton Boots

Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $148.50MSRP: $165

Sperry - Mini Lug Chukka. Color Other Brown. On sale for $105.00. MSRP $150.00. 30% off.

Sperry Mini Lug Chukka

Sperry Mini Lug Chukka

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Brown
Price: $105MSRP: $150

Kenneth Cole - Wilhem. Color Light Brown. On sale for $83.33. MSRP $164.95. 49% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Light Brown
Price: $83.33MSRP: $164.95

Kenneth Cole - Winston. Color Mocha Multi. On sale for $109.72. MSRP $159.95. 31% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Mocha Multi
Price: $109.72MSRP: $159.95

Sperry - Coldbay Chukka Realtree MM. Color Olive. On sale for $113.46. MSRP $120.00. 5% off.

Sperry Coldbay Chukka Realtree MM

Sperry Coldbay Chukka Realtree MM

Brand Name: Sperry
Product Name: Coldbay Chukka Realtree MM
Gender: Men's
Color: Olive
Price: $113.46MSRP: $120

FLY LONDON - Brak593fly. Color Black. Low Stock. On sale for $225.00. MSRP $250.00. 10% off. 4.5 out of 5 stars

Low Stock

FLY LONDON Brak593fly

FLY LONDON Brak593fly

Brand Name: FLY LONDON
Product Name: Brak593fly
Gender: Women's
Color: Black
Price: $225MSRP: $250

FLY LONDON - Brak593fly. Color Elephant. Low Stock. On sale for $152.75. MSRP $235.00. 35% off. 4.5 out of 5 stars

Low Stock

FLY LONDON Brak593fly

FLY LONDON Brak593fly

Brand Name: FLY LONDON
Product Name: Brak593fly
Gender: Women's
Color: Elephant
Price: $152.75MSRP: $235

Kenneth Cole - Wilhem. Color Mocha. On sale for $85.97. MSRP $164.95. 48% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Mocha
Price: $85.97MSRP: $164.95

Kenneth Cole - Winston. Color Dark Brown Multi. On sale for $108.23. MSRP $159.95. 32% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Dark Brown Multi
Price: $108.23MSRP: $159.95

Eastland 1955 Edition - Devin. Color Dark Brown. Low Stock. On sale for $60.23. MSRP $90.00. 33% off.

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: $60.23MSRP: $90

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $137.41. MSRP $194.95. 30% off. 4.0 out of 5 stars

ECCO Metropole Milan Chukka Boots

ECCO Metropole Milan Chukka Boots

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $137.41MSRP: $194.95

Cole Haan - Berkshire Chelsea Boots. Color Black/Truffle. Low Stock. On sale for $99.97. MSRP $250.00. 60% off. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Black/Truffle
Price: $99.97MSRP: $250

Cole Haan - Berkshire Chelsea Boots. Color Dark Sequoia/Natural. On sale for $135.38. MSRP $250.00. 46% off. 4.5 out of 5 stars

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Dark Sequoia/Natural
Price: $135.38MSRP: $250

Cole Haan - Berkshire Chelsea Boots. Color Lava Suede/Dark. Low Stock. On sale for $88.40. MSRP $250.00. 65% off. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Lava Suede/Dark
Price: $88.40MSRP: $250

ECCO - London Lace Up Waterproof Chukka Boots. Color Cocoa Brown Nubuck. Low Stock. On sale for $195.45. MSRP $229.95. 15% off. 4.0 out of 5 stars

Low Stock

ECCO London Lace Up Waterproof Chukka Boots

ECCO London Lace Up Waterproof Chukka Boots

Brand Name: ECCO
Product Name: London Lace Up Waterproof Chukka Boots
Gender: Men's
Color: Cocoa Brown Nubuck
Price: $195.45MSRP: $229.95