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

Men's Ankle Comfort Products

30 items found

Filters

Search Results

Dunham - Brisco. Color Medium Natural Leather. On sale for $47.98. MSRP $159.95. 70% off. 4.0 out of 5 stars

Dunham Brisco

Dunham Brisco

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Medium Natural Leather
Price: $47.98MSRP: $159.95

Dr. Martens - Anistone Lo Leather Boots. Color Sand. Low Stock. On sale for $51.00. MSRP $170.00. 70% off. 2.0 out of 5 stars

Low Stock

Dr. Martens Anistone Lo Leather Boots

Dr. Martens Anistone Lo Leather Boots

Brand Name: Dr. Martens
Product Name: Anistone Lo Leather Boots
Gender: Unisex
Color: Sand
Price: $51MSRP: $170

Crocs - Classic Rain Boot. Color Sunflower. Low Stock. On sale for $17.98. MSRP $59.95. 70% off. 4.3 out of 5 stars

Low Stock

Crocs Classic Rain Boot

Crocs Classic Rain Boot

Brand Name: Crocs
Product Name: Classic Rain Boot
Gender: Unisex
Color: Sunflower
Price: $17.98MSRP: $59.95

Eastland 1955 Edition - Finn. Color Tan. Low Stock. On sale for $27.00. MSRP $90.00. 70% off.

Low Stock

Eastland 1955 Edition Finn

Eastland 1955 Edition Finn

Brand Name: Eastland 1955 Edition
Product Name: Finn
Gender: Men's
Color: Tan
Price: $27MSRP: $90

Born - Ryker. Color Dark Grey. Low Stock. On sale for $45.00. MSRP $150.00. 70% off. 1.0 out of 5 stars

Low Stock

Born Ryker

Born Ryker

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Dark Grey
Price: $45MSRP: $150

Josef Seibel - Earl 12 Boots. Color Black. Low Stock. On sale for $51.00. MSRP $170.00. 70% off.

Low Stock

Josef Seibel Earl 12 Boots

Josef Seibel Earl 12 Boots

Brand Name: Josef Seibel
Product Name: Earl 12 Boots
Gender: Men's
Color: Black
Price: $51MSRP: $170

Johnston & Murphy - Barrett Chukka. Color Tan Full Grain. Low Stock. On sale for $52.50. MSRP $175.00. 70% off.

Low Stock

Johnston & Murphy Barrett Chukka

Johnston & Murphy Barrett Chukka

Brand Name: Johnston & Murphy
Product Name: Barrett Chukka
Gender: Men's
Color: Tan Full Grain
Price: $52.50MSRP: $175

Deer Stags - Rockland. Color Brown/Dark Brown. On sale for $58.48. MSRP $90.00. 35% off. 3.7 out of 5 stars

Deer Stags Rockland

Deer Stags Rockland

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Brown/Dark Brown
Price: $58.48MSRP: $90

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

Born - Lincoln. Color Black. On sale for $60.00. MSRP $100.00. 40% off.

Born Lincoln

Born Lincoln

Brand Name: Born
Product Name: Lincoln
Gender: Men's
Color: Black
Price: $60MSRP: $100

TOMS - Travel Lite Forrest. Color Tan. On sale for $58.50. MSRP $130.00. 55% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Tan
Price: $58.50MSRP: $130

Dockers - Denver. Color Tan. Low Stock. On sale for $25.50. MSRP $85.00. 70% off.

Low Stock

Dockers Denver

Dockers Denver

Brand Name: Dockers
Product Name: Denver
Gender: Men's
Color: Tan
Price: $25.50MSRP: $85

Deer Stags - Rockland. Color Redwood/Dark Brown. On sale for $58.50. MSRP $90.00. 35% off. 3.7 out of 5 stars

Deer Stags Rockland

Deer Stags Rockland

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Redwood/Dark Brown
Price: $58.50MSRP: $90

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $50.45. MSRP $90.00. 44% off. 3.9 out of 5 stars

Deer Stags Bangor

Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $50.45MSRP: $90

Deer Stags - Argos. Color Black/Blue. On sale for $51.00. MSRP $100.00. 49% off. 3.7 out of 5 stars

Deer Stags Argos

Deer Stags Argos

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Black/Blue
Price: $51MSRP: $100

Vans - U MTE™ Crestline Waterproof. Color Frost Gray. Low Stock. On sale for $49.50. MSRP $165.00. 70% off. 5.0 out of 5 stars

Low Stock

Vans U MTE™ Crestline Waterproof

Vans U MTE™ Crestline Waterproof

Brand Name: Vans
Product Name: U MTE™ Crestline Waterproof
Gender: Unisex
Color: Frost Gray
Price: $49.50MSRP: $165

UGG - Biltmore Chelsea. Color Chestnut Suede. Low Stock. On sale for $43.65. MSRP $149.95. 71% off. 4.4 out of 5 stars

Low Stock

UGG Biltmore Chelsea

UGG Biltmore Chelsea

Brand Name: UGG
Product Name: Biltmore Chelsea
Gender: Men's
Color: Chestnut Suede
Price: $43.65MSRP: $149.95

DieHard - Charger. Color Brown. Low Stock. On sale for $59.97. MSRP $119.95. 50% off. 1.0 out of 5 stars

Low Stock

DieHard Charger

DieHard Charger

Brand Name: DieHard
Product Name: Charger
Gender: Men's
Color: Brown
Price: $59.97MSRP: $119.95

Crocs - Crush Rain Boot. Color Grass Green. Low Stock. On sale for $23.98. MSRP $79.95. 70% off. 4.3 out of 5 stars

Low Stock

Crocs Crush Rain Boot

Crocs Crush Rain Boot

Brand Name: Crocs
Product Name: Crush Rain Boot
Gender: Unisex
Color: Grass Green
Price: $23.98MSRP: $79.95

Crocs - Classic Rain Boot. Color Black. On sale for $35.97. MSRP $59.95. 40% off. 4.3 out of 5 stars

Crocs Classic Rain Boot

Crocs Classic Rain Boot

Brand Name: Crocs
Product Name: Classic Rain Boot
Gender: Unisex
Color: Black
Price: $35.97MSRP: $59.95

Crocs - Crush Rain Boot. Color Atmosphere/Glitter. Low Stock. On sale for $25.48. MSRP $84.95. 70% off. 4.3 out of 5 stars

Low Stock

Crocs Crush Rain Boot

Crocs Crush Rain Boot

Brand Name: Crocs
Product Name: Crush Rain Boot
Gender: Unisex
Color: Atmosphere/Glitter
Price: $25.48MSRP: $84.95

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

Nunn Bush - Grazie AP1 Work Slip-On Slip-Resistant Work Shoe EZ On Athletic Style Sneaker. Color Black. On sale for $59.95. MSRP $90.00. 33% off. 1.0 out of 5 stars

Nunn Bush Grazie AP1 Work Slip-On Slip-Resistant Work Shoe EZ On Athletic Style Sneaker

Nunn Bush Grazie AP1 Work Slip-On Slip-Resistant Work Shoe EZ On Athletic Style Sneaker

Brand Name: Nunn Bush
Product Name: Grazie AP1 Work Slip-On Slip-Resistant Work Shoe EZ On Athletic Style Sneaker
Gender: Men's
Color: Black
Price: $59.95MSRP: $90

Merrell - Alpine 83 Sneaker Recraft Mid Waterproof. Color Durum. Low Stock. On sale for $50.05. MSRP $125.00. 60% off. 3.4 out of 5 stars

Low Stock

Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Brand Name: Merrell
Product Name: Alpine 83 Sneaker Recraft Mid Waterproof
Gender: Men's
Color: Durum
Price: $50.05MSRP: $125

Eastland 1955 Edition - Hugo. Color Brown. Low Stock. On sale for $30.00. MSRP $100.00. 70% off.

Low Stock

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Brown
Price: $30MSRP: $100

Marc Joseph New York - Crosby Boots. Color Cognac Grainy. Low Stock. On sale for $58.50. MSRP $195.00. 70% off. 5.0 out of 5 stars

Low Stock

Marc Joseph New York Crosby Boots

Marc Joseph New York Crosby Boots

Brand Name: Marc Joseph New York
Product Name: Crosby Boots
Gender: Men's
Color: Cognac Grainy
Price: $58.50MSRP: $195

Dr. Scholl's - Russell. Color Black Faux Leather. Low Stock. On sale for $55.25. MSRP $85.00. 35% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Russell

Dr. Scholl's Russell

Brand Name: Dr. Scholl's
Product Name: Russell
Gender: Men's
Color: Black Faux Leather
Price: $55.25MSRP: $85

TOMS - Palomar. Color Oak Brown Waxed Canvas/Leather. Low Stock. On sale for $55.50. MSRP $185.00. 70% off.

Low Stock

TOMS Palomar

TOMS Palomar

Brand Name: TOMS
Product Name: Palomar
Gender: Men's
Color: Oak Brown Waxed Canvas/Leather
Price: $55.50MSRP: $185

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. Low Stock. On sale for $57.50. MSRP $115.00. 50% off. 4.3 out of 5 stars

Low Stock

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $57.50MSRP: $115

Xero Shoes - Daylite Hiker Fusion. Color Black. On sale for $53.99. MSRP $119.99. 55% off. 4.4 out of 5 stars

Xero Shoes Daylite Hiker Fusion

Xero Shoes Daylite Hiker Fusion

Brand Name: Xero Shoes
Product Name: Daylite Hiker Fusion
Gender: Men's
Color: Black
Price: $53.99MSRP: $119.99