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 Casual Comfort GUESS Products

42 items found

Filters

Search Results

GUESS - Connee. Color Black. On sale for $65.45. MSRP $119.00. 45% off.

GUESS Connee

GUESS Connee

Brand Name: GUESS
Product Name: Connee
Gender: Women's
Color: Black
Price: $65.45MSRP: $119

GUESS - Gables. Color Light Natural. Low Stock. On sale for $29.70. MSRP $99.00. 70% off. 5.0 out of 5 stars

Low Stock

GUESS Gables

GUESS Gables

Brand Name: GUESS
Product Name: Gables
Gender: Women's
Color: Light Natural
Price: $29.70MSRP: $99

GUESS - Joezi. Color Black Synthetic. On sale for $59.40. MSRP $99.00. 40% off.

GUESS Joezi

GUESS Joezi

Brand Name: GUESS
Product Name: Joezi
Gender: Women's
Color: Black Synthetic
Price: $59.40MSRP: $99

GUESS - Loui. Color Dark Red Synthetic. On sale for $60.00. MSRP $75.00. 20% off.

GUESS Loui

GUESS Loui

Brand Name: GUESS
Product Name: Loui
Gender: Women's
Color: Dark Red Synthetic
Price: $60MSRP: $75

GUESS - Gallai. Color Gold. Low Stock. On sale for $62.30. MSRP $89.00. 30% off.

Low Stock

GUESS Gallai

GUESS Gallai

Brand Name: GUESS
Product Name: Gallai
Gender: Women's
Color: Gold
Price: $62.30MSRP: $89

GUESS - Britz. Color White. On sale for $58.19. MSRP $89.00. 35% off. 3.0 out of 5 stars

GUESS Britz

GUESS Britz

Brand Name: GUESS
Product Name: Britz
Gender: Women's
Color: White
Price: $58.19MSRP: $89

GUESS - Britz. Color Black. On sale for $62.64. MSRP $89.00. 30% off. 3.0 out of 5 stars

GUESS Britz

GUESS Britz

Brand Name: GUESS
Product Name: Britz
Gender: Women's
Color: Black
Price: $62.64MSRP: $89

GUESS - Guinna. Color Leopard. On sale for $45.15. MSRP $129.00. 65% off.

GUESS Guinna

GUESS Guinna

Brand Name: GUESS
Product Name: Guinna
Gender: Women's
Color: Leopard
Price: $45.15MSRP: $129

GUESS - Elyho. Color Rose Gold. On sale for $44.25. MSRP $59.00. 25% off. 5.0 out of 5 stars

GUESS Elyho

GUESS Elyho

Brand Name: GUESS
Product Name: Elyho
Gender: Women's
Color: Rose Gold
Price: $44.25MSRP: $59

GUESS - Luseray. Color Dark Brown Croco. On sale for $71.40. MSRP $119.00. 40% off. 5.0 out of 5 stars

GUESS Luseray

GUESS Luseray

Brand Name: GUESS
Product Name: Luseray
Gender: Women's
Color: Dark Brown Croco
Price: $71.40MSRP: $119

GUESS - Deinna. Color Medium Brown. Low Stock. On sale for $54.35. MSRP $99.00. 45% off.

Low Stock

GUESS Deinna

GUESS Deinna

Brand Name: GUESS
Product Name: Deinna
Gender: Women's
Color: Medium Brown
Price: $54.35MSRP: $99

GUESS - Paxey. Color Black. On sale for $60.20. MSRP $99.00. 39% off.

GUESS Paxey

GUESS Paxey

Brand Name: GUESS
Product Name: Paxey
Gender: Women's
Color: Black
Price: $60.20MSRP: $99

GUESS - Ocilia. Color Black 1. Low Stock. On sale for $35.70. MSRP $119.00. 70% off. 5.0 out of 5 stars

Low Stock

GUESS Ocilia

GUESS Ocilia

Brand Name: GUESS
Product Name: Ocilia
Gender: Women's
Color: Black 1
Price: $35.70MSRP: $119

GUESS - Graydee. Color Black. Low Stock. On sale for $49.87. MSRP $99.00. 50% off. 5.0 out of 5 stars

Low Stock

GUESS Graydee

GUESS Graydee

Brand Name: GUESS
Product Name: Graydee
Gender: Women's
Color: Black
Price: $49.87MSRP: $99

GUESS - Graydee. Color Ivory. On sale for $67.45. MSRP $99.00. 32% off. 5.0 out of 5 stars

GUESS Graydee

GUESS Graydee

Brand Name: GUESS
Product Name: Graydee
Gender: Women's
Color: Ivory
Price: $67.45MSRP: $99

GUESS - Elowen. Color Bronze. Low Stock. On sale for $43.76. MSRP $55.00. 20% off.

Low Stock

GUESS Elowen

GUESS Elowen

Brand Name: GUESS
Product Name: Elowen
Gender: Women's
Color: Bronze
Price: $43.76MSRP: $55

GUESS - Elowen. Color Black. Low Stock. On sale for $35.75. MSRP $55.00. 35% off.

Low Stock

GUESS Elowen

GUESS Elowen

Brand Name: GUESS
Product Name: Elowen
Gender: Women's
Color: Black
Price: $35.75MSRP: $55

GUESS - Carey. Color Medium Pink Logo. Low Stock. On sale for $63.60. MSRP $89.00. 29% off.

Low Stock

GUESS Carey

GUESS Carey

Brand Name: GUESS
Product Name: Carey
Gender: Women's
Color: Medium Pink Logo
Price: $63.60MSRP: $89

GUESS - Saima. Color Black Crystal. On sale for $64.35. MSRP $99.00. 35% off.

GUESS Saima

GUESS Saima

Brand Name: GUESS
Product Name: Saima
Gender: Women's
Color: Black Crystal
Price: $64.35MSRP: $99

GUESS - Elyho. Color Medium Pink. On sale for $38.28. MSRP $59.00. 35% off. 5.0 out of 5 stars

GUESS Elyho

GUESS Elyho

Brand Name: GUESS
Product Name: Elyho
Gender: Women's
Color: Medium Pink
Price: $38.28MSRP: $59

GUESS - Elyho. Color Ivory. On sale for $39.00. MSRP $59.00. 34% off. 5.0 out of 5 stars

GUESS Elyho

GUESS Elyho

Brand Name: GUESS
Product Name: Elyho
Gender: Women's
Color: Ivory
Price: $39MSRP: $59

GUESS - Mayan. Color Bronze. On sale for $71.36. MSRP $99.00. 28% off. 4.0 out of 5 stars

GUESS Mayan

GUESS Mayan

Brand Name: GUESS
Product Name: Mayan
Gender: Women's
Color: Bronze
Price: $71.36MSRP: $99

GUESS - Bommiya. Color Ivory. Low Stock. On sale for $66.43. MSRP $89.00. 25% off. 4.0 out of 5 stars

Low Stock

GUESS Bommiya

GUESS Bommiya

Brand Name: GUESS
Product Name: Bommiya
Gender: Women's
Color: Ivory
Price: $66.43MSRP: $89

GUESS - Saima. Color Silver Crystal. On sale for $44.55. MSRP $99.00. 55% off.

GUESS Saima

GUESS Saima

Brand Name: GUESS
Product Name: Saima
Gender: Women's
Color: Silver Crystal
Price: $44.55MSRP: $99

GUESS - Charmin. Color Black. On sale for $66.77. MSRP $119.00. 44% off.

GUESS Charmin

GUESS Charmin

Brand Name: GUESS
Product Name: Charmin
Gender: Women's
Color: Black
Price: $66.77MSRP: $119

GUESS - Fonzi. Color Ivory Synthetic. Low Stock. On sale for $54.50. MSRP $119.00. 54% off.

Low Stock

GUESS Fonzi

GUESS Fonzi

Brand Name: GUESS
Product Name: Fonzi
Gender: Women's
Color: Ivory Synthetic
Price: $54.50MSRP: $119

GUESS - Yanika. Color Black 1 Synthetic. Low Stock. On sale for $59.50. MSRP $119.00. 50% off. 3.5 out of 5 stars

Low Stock

GUESS Yanika

GUESS Yanika

Brand Name: GUESS
Product Name: Yanika
Gender: Women's
Color: Black 1 Synthetic
Price: $59.50MSRP: $119

GUESS - Kalidal. Color White Faux Leather. On sale for $47.53. MSRP $119.00. 60% off. 5.0 out of 5 stars

GUESS Kalidal

GUESS Kalidal

Brand Name: GUESS
Product Name: Kalidal
Gender: Women's
Color: White Faux Leather
Price: $47.53MSRP: $119

GUESS - Franiely. Color Brown Genuine Cow Leather. On sale for $49.50. MSRP $99.00. 50% off. 3.0 out of 5 stars

GUESS Franiely

GUESS Franiely

Brand Name: GUESS
Product Name: Franiely
Gender: Women's
Color: Brown Genuine Cow Leather
Price: $49.50MSRP: $99

GUESS - Yanika. Color Brown Leather. Low Stock. On sale for $59.50. MSRP $119.00. 50% off. 3.5 out of 5 stars

Low Stock

GUESS Yanika

GUESS Yanika

Brand Name: GUESS
Product Name: Yanika
Gender: Women's
Color: Brown Leather
Price: $59.50MSRP: $119

GUESS - Yanika. Color Black Synthetic. Low Stock. On sale for $59.50. MSRP $119.00. 50% off. 3.5 out of 5 stars

Low Stock

GUESS Yanika

GUESS Yanika

Brand Name: GUESS
Product Name: Yanika
Gender: Women's
Color: Black Synthetic
Price: $59.50MSRP: $119

GUESS - Joezi. Color White Synthetic. On sale for $60.41. MSRP $99.00. 39% off.

GUESS Joezi

GUESS Joezi

Brand Name: GUESS
Product Name: Joezi
Gender: Women's
Color: White Synthetic
Price: $60.41MSRP: $99

GUESS - Franie. Color Red Synthetic. On sale for $60.75. MSRP $99.00. 39% off.

GUESS Franie

GUESS Franie

Brand Name: GUESS
Product Name: Franie
Gender: Women's
Color: Red Synthetic
Price: $60.75MSRP: $99

GUESS - Naska. Color Black Synthetic. Low Stock. On sale for $58.05. MSRP $129.00. 55% off. 3.0 out of 5 stars

Low Stock

GUESS Naska

GUESS Naska

Brand Name: GUESS
Product Name: Naska
Gender: Women's
Color: Black Synthetic
Price: $58.05MSRP: $129

GUESS - Isaac. Color Gold Leather. Low Stock. On sale for $26.70. MSRP $89.00. 70% off. 3.0 out of 5 stars

Low Stock

GUESS Isaac

GUESS Isaac

Brand Name: GUESS
Product Name: Isaac
Gender: Women's
Color: Gold Leather
Price: $26.70MSRP: $89

GUESS - Zands. Color Dark Red Patent. Low Stock. On sale for $44.50. MSRP $89.00. 50% off. 2.0 out of 5 stars

Low Stock

GUESS Zands

GUESS Zands

Brand Name: GUESS
Product Name: Zands
Gender: Women's
Color: Dark Red Patent
Price: $44.50MSRP: $89

GUESS - Charmer. Color Silver Rubber. On sale for $71.40. MSRP $119.00. 40% off.

GUESS Charmer

GUESS Charmer

Brand Name: GUESS
Product Name: Charmer
Gender: Women's
Color: Silver Rubber
Price: $71.40MSRP: $119

GUESS - Damani. Color Light Pink. Low Stock. On sale for $56.23. MSRP $99.00. 43% off. 4.0 out of 5 stars

Low Stock

GUESS Damani

GUESS Damani

Brand Name: GUESS
Product Name: Damani
Gender: Women's
Color: Light Pink
Price: $56.23MSRP: $99

GUESS - Damani. Color Black. Low Stock. On sale for $59.40. MSRP $99.00. 40% off. 4.0 out of 5 stars

Low Stock

GUESS Damani

GUESS Damani

Brand Name: GUESS
Product Name: Damani
Gender: Women's
Color: Black
Price: $59.40MSRP: $99

GUESS - Loui. Color Light Natural Synthetic. Low Stock. On sale for $52.50. MSRP $75.00. 30% off.

Low Stock

GUESS Loui

GUESS Loui

Brand Name: GUESS
Product Name: Loui
Gender: Women's
Color: Light Natural Synthetic
Price: $52.50MSRP: $75

GUESS - Loui. Color Black Synthetic. Low Stock. On sale for $52.50. MSRP $75.00. 30% off.

Low Stock

GUESS Loui

GUESS Loui

Brand Name: GUESS
Product Name: Loui
Gender: Women's
Color: Black Synthetic
Price: $52.50MSRP: $75

GUESS - Funzya. Color Medium Blue Denim Patchwork. On sale for $65.68. MSRP $129.00. 49% off.

GUESS Funzya

GUESS Funzya

Brand Name: GUESS
Product Name: Funzya
Gender: Women's
Color: Medium Blue Denim Patchwork
Price: $65.68MSRP: $129