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

Leather Casual Sperry Shoes

43 items found

Sort By

Your Selections

Search Results

Sperry - Leeward II (Little Kid/Big Kid). Color Sahara 3. On sale for $30.22. MSRP $54.95. 45% off. 5.0 out of 5 stars

Sperry Leeward II (Little Kid/Big Kid)

Sperry Leeward II (Little Kid/Big Kid)

Brand Name: Sperry
Product Name: Leeward II (Little Kid/Big Kid)
Color: Sahara 3
Price: $30.22MSRP: $54.95

Sperry - Avenue Duck Boot. Color Black/Amaretto. On sale for $83.95. MSRP $120.00. 30% off. 4.1 out of 5 stars

Sperry Avenue Duck Boot

Sperry Avenue Duck Boot

Brand Name: Sperry
Product Name: Avenue Duck Boot
Gender: Men's
Color: Black/Amaretto
Price: $83.95MSRP: $120

Sperry - Saltwater 2.0 Leather. Color Dark Brown. On sale for $39.98. MSRP $120.00. 67% off. 4.3 out of 5 stars

Sperry Saltwater 2.0 Leather

Sperry Saltwater 2.0 Leather

Brand Name: Sperry
Product Name: Saltwater 2.0 Leather
Gender: Women's
Color: Dark Brown
Price: $39.98MSRP: $120

Sperry - Port Driving Moccasin. Color Silver. Low Stock. On sale for $30.00. MSRP $100.00. 70% off. 4.0 out of 5 stars

Low Stock

Sperry Port Driving Moccasin

Sperry Port Driving Moccasin

Brand Name: Sperry
Product Name: Port Driving Moccasin
Gender: Women's
Color: Silver
Price: $30MSRP: $100

Sperry - Wedge Cupsole Penny Ladies. Color Navy. Low Stock. On sale for $33.00. MSRP $110.00. 70% off. 5.0 out of 5 stars

Low Stock

Sperry Wedge Cupsole Penny Ladies

Sperry Wedge Cupsole Penny Ladies

Brand Name: Sperry
Product Name: Wedge Cupsole Penny Ladies
Gender: Women's
Color: Navy
Price: $33MSRP: $110

Sperry - Billfish 3-Eye Boat Shoe. Color Dark Tan. On sale for $71.00. MSRP $110.00. 35% off. 4.3 out of 5 stars

Sperry Billfish 3-Eye Boat Shoe

Sperry Billfish 3-Eye Boat Shoe

Brand Name: Sperry
Product Name: Billfish 3-Eye Boat Shoe
Gender: Men's
Color: Dark Tan
Price: $71MSRP: $110

Sperry - Coastal Break Chukka (Toddler/Little Kid). Color Tan. Low Stock. On sale for $15.00. MSRP $50.00. 70% off. 4.2 out of 5 stars

Low Stock

Sperry Coastal Break Chukka (Toddler/Little Kid)

Sperry Coastal Break Chukka (Toddler/Little Kid)

Brand Name: Sperry
Product Name: Coastal Break Chukka (Toddler/Little Kid)
Color: Tan
Price: $15MSRP: $50

Sperry - A/O 2-Eye Double Sole Nubuck. Color Brown. Low Stock. On sale for $55.00. MSRP $110.00. 50% off.

Low Stock

Sperry A/O 2-Eye Double Sole Nubuck

Sperry A/O 2-Eye Double Sole Nubuck

Brand Name: Sperry
Product Name: A/O 2-Eye Double Sole Nubuck
Gender: Men's
Color: Brown
Price: $55MSRP: $110

Sperry - A/O Plushwave Lug Chukka. Color Black 2. Low Stock. On sale for $42.00. MSRP $140.00. 70% off. 4.1 out of 5 stars

Low Stock

Sperry A/O Plushwave Lug Chukka

Sperry A/O Plushwave Lug Chukka

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Gender: Men's
Color: Black 2
Price: $42MSRP: $140

Sperry - Leeward II (Little Kid/Big Kid). Color Sahara 2. On sale for $38.46. MSRP $54.95. 30% off. 5.0 out of 5 stars

Sperry Leeward II (Little Kid/Big Kid)

Sperry Leeward II (Little Kid/Big Kid)

Brand Name: Sperry
Product Name: Leeward II (Little Kid/Big Kid)
Color: Sahara 2
Price: $38.46MSRP: $54.95

Sperry - Saltwater 1-Eye Cozy. Color Black/Black. Low Stock. On sale for $26.25. MSRP $105.00. 75% off. 4.6 out of 5 stars

Low Stock

Sperry Saltwater 1-Eye Cozy

Sperry Saltwater 1-Eye Cozy

Brand Name: Sperry
Product Name: Saltwater 1-Eye Cozy
Gender: Women's
Color: Black/Black
Price: $26.25MSRP: $105

Sperry - A/O 2-Eye Plushwave. Color Brown. Low Stock. On sale for $76.96. MSRP $110.00. 30% off. 4.0 out of 5 stars

Low Stock

Sperry A/O 2-Eye Plushwave

Sperry A/O 2-Eye Plushwave

Brand Name: Sperry
Product Name: A/O 2-Eye Plushwave
Gender: Men's
Color: Brown
Price: $76.96MSRP: $110

Sperry - Racquet Oxford. Color Blue. $74.95.

Sperry Racquet Oxford

Sperry Racquet Oxford

Brand Name: Sperry
Product Name: Racquet Oxford
Gender: Men's
Color: Blue
Price: $74.95

Sperry - Saltwater Ch. Color Dark Brown. Low Stock. On sale for $97.05. MSRP $120.00. 19% off. 3.0 out of 5 stars

Low Stock

Sperry Saltwater Ch

Sperry Saltwater Ch

Brand Name: Sperry
Product Name: Saltwater Ch
Gender: Women's
Color: Dark Brown
Price: $97.05MSRP: $120

Sperry - Waveside Plushwave Backstrap. Color Ivory. On sale for $53.38. MSRP $65.00. 18% off. 3.5 out of 5 stars

Sperry Waveside Plushwave Backstrap

Sperry Waveside Plushwave Backstrap

Brand Name: Sperry
Product Name: Waveside Plushwave Backstrap
Gender: Women's
Color: Ivory
Price: $53.38MSRP: $65

Sperry - Cami Flatform. Color Tan. Low Stock. On sale for $85.00. MSRP $95.00. 11% off. 3.8 out of 5 stars

Low Stock

Sperry Cami Flatform

Sperry Cami Flatform

Brand Name: Sperry
Product Name: Cami Flatform
Gender: Women's
Color: Tan
Price: $85MSRP: $95

Sperry - Spinnaker Washable (Little Kid/Big Kid). Color Khaki. On sale for $34.14. MSRP $40.00. 15% off. 4.3 out of 5 stars

Sperry Spinnaker Washable (Little Kid/Big Kid)

Sperry Spinnaker Washable (Little Kid/Big Kid)

Brand Name: Sperry
Product Name: Spinnaker Washable (Little Kid/Big Kid)
Color: Khaki
Price: $34.14MSRP: $40

Sperry - Racquet Oxford. Color White. $89.95.

Sperry Racquet Oxford

Sperry Racquet Oxford

Brand Name: Sperry
Product Name: Racquet Oxford
Gender: Men's
Color: White
Price: $89.95

Sperry - Spinnaker Washable (Little Kid/Big Kid). Color Grey 2. Low Stock. On sale for $47.23. MSRP $50.00. 6% off. 4.3 out of 5 stars

Low Stock

Sperry Spinnaker Washable (Little Kid/Big Kid)

Sperry Spinnaker Washable (Little Kid/Big Kid)

Brand Name: Sperry
Product Name: Spinnaker Washable (Little Kid/Big Kid)
Color: Grey 2
Price: $47.23MSRP: $50

Sperry - Authentic Original Slip On (Toddler/Little Kids). Color Sahara Leather. On sale for $52.78. MSRP $59.95. 12% off. 3.9 out of 5 stars

Sperry Authentic Original Slip On (Toddler/Little Kids)

Sperry Authentic Original Slip On (Toddler/Little Kids)

Brand Name: Sperry
Product Name: Authentic Original Slip On (Toddler/Little Kids)
Color: Sahara Leather
Price: $52.78MSRP: $59.95

Sperry - Seaportpenny. Color Brown Primary - Multi. On sale for $77.00. MSRP $110.00. 30% off. 4.0 out of 5 stars

Sperry Seaportpenny

Sperry Seaportpenny

Brand Name: Sperry
Product Name: Seaportpenny
Gender: Women's
Color: Brown Primary - Multi
Price: $77MSRP: $110

Sperry - Surveyor 2-Eye. Color Grey. Low Stock. On sale for $76.50. MSRP $85.00. 10% off. 2.5 out of 5 stars

Low Stock

Sperry Surveyor 2-Eye

Sperry Surveyor 2-Eye

Brand Name: Sperry
Product Name: Surveyor 2-Eye
Gender: Men's
Color: Grey
Price: $76.50MSRP: $85

Sperry - Waveside Plushwave Slide. Color Ivory. Low Stock. On sale for $49.31. MSRP $60.00. 18% off. 3.9 out of 5 stars

Low Stock

Sperry Waveside Plushwave Slide

Sperry Waveside Plushwave Slide

Brand Name: Sperry
Product Name: Waveside Plushwave Slide
Gender: Women's
Color: Ivory
Price: $49.31MSRP: $60

Sperry - Davenport Venetian. Color Brown. Low Stock. On sale for $98.95. MSRP $109.95. 10% off. 3.9 out of 5 stars

Low Stock

Sperry Davenport Venetian

Sperry Davenport Venetian

Brand Name: Sperry
Product Name: Davenport Venetian
Gender: Men's
Color: Brown
Price: $98.95MSRP: $109.95

Sperry - Crest Vibe Washable. Color Navy. Low Stock. On sale for $42.50. MSRP $85.00. 50% off. 4.3 out of 5 stars

Low Stock

Sperry Crest Vibe Washable

Sperry Crest Vibe Washable

Brand Name: Sperry
Product Name: Crest Vibe Washable
Gender: Women's
Color: Navy
Price: $42.50MSRP: $85

Sperry - Shoresider Jr. (Toddler/Little Kid). Color Linen/Oat. $49.99.

Sperry Shoresider Jr. (Toddler/Little Kid)

Sperry Shoresider Jr. (Toddler/Little Kid)

Brand Name: Sperry
Product Name: Shoresider Jr. (Toddler/Little Kid)
Color: Linen/Oat
Price: $49.99

Sperry - Saltwater Boot (Little Kid/Big Kid). Color Brown/Brown. On sale for $54.62. MSRP $75.00. 27% off. 4.4 out of 5 stars

Sperry Saltwater Boot (Little Kid/Big Kid)

Sperry Saltwater Boot (Little Kid/Big Kid)

Brand Name: Sperry
Product Name: Saltwater Boot (Little Kid/Big Kid)
Color: Brown/Brown
Price: $54.62MSRP: $75

Sperry - Port Driver. Color Tan. Low Stock. On sale for $90.00. MSRP $100.00. 10% off.

Low Stock

Sperry Port Driver

Sperry Port Driver

Brand Name: Sperry
Product Name: Port Driver
Gender: Women's
Color: Tan
Price: $90MSRP: $100

Sperry - Candy Boat. Color Other Beige. On sale for $42.50. MSRP $85.00. 50% off.

Sperry Candy Boat

Sperry Candy Boat

Brand Name: Sperry
Product Name: Candy Boat
Gender: Women's
Color: Other Beige
Price: $42.50MSRP: $85

Sperry - AO 2 Eye. Color Tan 1. On sale for $82.50. MSRP $110.00. 25% off. 4.5 out of 5 stars

Sperry AO 2 Eye

Sperry AO 2 Eye

Brand Name: Sperry
Product Name: AO 2 Eye
Gender: Women's
Color: Tan 1
Price: $82.50MSRP: $110

Sperry - Mini Lug Chukka. Color Other Brown. On sale for $75.00. MSRP $150.00. 50% off.

Sperry Mini Lug Chukka

Sperry Mini Lug Chukka

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Brown
Price: $75MSRP: $150

Sperry - AO 2 Eye. Color Navy 2. On sale for $66.00. MSRP $110.00. 40% off. 4.5 out of 5 stars

Sperry AO 2 Eye

Sperry AO 2 Eye

Brand Name: Sperry
Product Name: AO 2 Eye
Gender: Women's
Color: Navy 2
Price: $66MSRP: $110

Sperry - Angelfish 2-Eye. Color Tan Multi. Low Stock. On sale for $89.34. MSRP $100.00. 11% off. 3.1 out of 5 stars

Low Stock

Sperry Angelfish 2-Eye

Sperry Angelfish 2-Eye

Brand Name: Sperry
Product Name: Angelfish 2-Eye
Gender: Women's
Color: Tan Multi
Price: $89.34MSRP: $100

Sperry - A/O 3-Eye Vibram. Color Tan. Low Stock. On sale for $74.95. MSRP $149.95. 50% off. 4.8 out of 5 stars

Low Stock

Sperry A/O 3-Eye Vibram

Sperry A/O 3-Eye Vibram

Brand Name: Sperry
Product Name: A/O 3-Eye Vibram
Gender: Men's
Color: Tan
Price: $74.95MSRP: $149.95

Sperry - Candy Lace-To-Toe. Color Ecru. On sale for $59.99. MSRP $85.00. 29% off.

Sperry Candy Lace-To-Toe

Sperry Candy Lace-To-Toe

Brand Name: Sperry
Product Name: Candy Lace-To-Toe
Gender: Women's
Color: Ecru
Price: $59.99MSRP: $85

Sperry - Port Driving Moccasin. Color Bone. Low Stock. On sale for $70.00. MSRP $100.00. 30% off. 4.0 out of 5 stars

Low Stock

Sperry Port Driving Moccasin

Sperry Port Driving Moccasin

Brand Name: Sperry
Product Name: Port Driving Moccasin
Gender: Women's
Color: Bone
Price: $70MSRP: $100

Sperry - Wells Boat. Color Cream. On sale for $55.00. MSRP $110.00. 50% off. 3.0 out of 5 stars

Sperry Wells Boat

Sperry Wells Boat

Brand Name: Sperry
Product Name: Wells Boat
Gender: Women's
Color: Cream
Price: $55MSRP: $110

Sperry - AO 2 Eye. Color Gold. On sale for $88.29. MSRP $100.00. 12% off. 4.5 out of 5 stars

Sperry AO 2 Eye

Sperry AO 2 Eye

Brand Name: Sperry
Product Name: AO 2 Eye
Gender: Women's
Color: Gold
Price: $88.29MSRP: $100

Sperry - Wedge Cupsole Penny Ladies. Color White. On sale for $55.00. MSRP $110.00. 50% off. 5.0 out of 5 stars

Sperry Wedge Cupsole Penny Ladies

Sperry Wedge Cupsole Penny Ladies

Brand Name: Sperry
Product Name: Wedge Cupsole Penny Ladies
Gender: Women's
Color: White
Price: $55MSRP: $110

Sperry - Rockyhikerwl. Color Black. On sale for $97.50. MSRP $150.00. 35% off.

Sperry Rockyhikerwl

Sperry Rockyhikerwl

Brand Name: Sperry
Product Name: Rockyhikerwl
Gender: Women's
Color: Black
Price: $97.50MSRP: $150

Sperry - Rockyhikerwl. Color Medium Brown. On sale for $75.00. MSRP $150.00. 50% off.

Sperry Rockyhikerwl

Sperry Rockyhikerwl

Brand Name: Sperry
Product Name: Rockyhikerwl
Gender: Women's
Color: Medium Brown
Price: $75MSRP: $150

Sperry - AO 2 Eye. Color Light Pink. On sale for $60.50. MSRP $110.00. 45% off. 4.5 out of 5 stars

Sperry AO 2 Eye

Sperry AO 2 Eye

Brand Name: Sperry
Product Name: AO 2 Eye
Gender: Women's
Color: Light Pink
Price: $60.50MSRP: $110

Sperry - AO 2 Eye. Color Brown Primary/Multi. On sale for $55.00. MSRP $110.00. 50% off. 4.5 out of 5 stars

Sperry AO 2 Eye

Sperry AO 2 Eye

Brand Name: Sperry
Product Name: AO 2 Eye
Gender: Women's
Color: Brown Primary/Multi
Price: $55MSRP: $110