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 or Less!

Shop Boot Deals

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

Massimo Matteo Loafers

31 items found

Sort By

Your Selections

Search Results

Massimo Matteo - Bit Strap Driver. Color Black. On sale for $38.35. MSRP $59.00.. 4.2 out of 5 stars

Massimo Matteo Bit Strap Driver

Massimo Matteo Bit Strap Driver

Brand Name: Massimo Matteo
Product Name: Bit Strap Driver
Gender: Men's
Color: Black
Price: $38.35MSRP: $59.00

Massimo Matteo - Florencia Penny Driver. Color Black. Low Stock. On sale for $44.25. MSRP $59.00.. 4.2 out of 5 stars

Low Stock

Massimo Matteo Florencia Penny Driver

Massimo Matteo Florencia Penny Driver

Brand Name: Massimo Matteo
Product Name: Florencia Penny Driver
Gender: Men's
Color: Black
Price: $44.25MSRP: $59.00

Massimo Matteo - Florencia Penny Driver. Color Medium Brown. Low Stock. On sale for $44.25. MSRP $59.00.. 4.2 out of 5 stars

Low Stock

Massimo Matteo Florencia Penny Driver

Massimo Matteo Florencia Penny Driver

Brand Name: Massimo Matteo
Product Name: Florencia Penny Driver
Gender: Men's
Color: Medium Brown
Price: $44.25MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Grey Nubuck. On sale for $30.65. MSRP $59.00.. 3.9 out of 5 stars

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Grey Nubuck
Price: $30.65MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Tobacco Nubuck. Low Stock. On sale for $37.76. MSRP $59.00.. 3.9 out of 5 stars

Low Stock

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Tobacco Nubuck
Price: $37.76MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Amarelo Nubuck. On sale for $39.49. MSRP $59.00.. 3.9 out of 5 stars

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Amarelo Nubuck
Price: $39.49MSRP: $59.00

Massimo Matteo - Venetian Driver. Color Camel Nubuck. On sale for $40.95. MSRP $65.00.. 4.3 out of 5 stars

Massimo Matteo Venetian Driver

Massimo Matteo Venetian Driver

Brand Name: Massimo Matteo
Product Name: Venetian Driver
Gender: Men's
Color: Camel Nubuck
Price: $40.95MSRP: $65.00

Massimo Matteo - Perf Venetian Driver. Color Tan Nubuck. Low Stock. On sale for $41.26. MSRP $59.00.. 3.7 out of 5 stars

Low Stock

Massimo Matteo Perf Venetian Driver

Massimo Matteo Perf Venetian Driver

Brand Name: Massimo Matteo
Product Name: Perf Venetian Driver
Gender: Women's
Color: Tan Nubuck
Price: $41.26MSRP: $59.00

Massimo Matteo - Perf Venetian Driver. Color Amarelo Nubuck. Low Stock. On sale for $41.85. MSRP $59.00.. 3.7 out of 5 stars

Low Stock

Massimo Matteo Perf Venetian Driver

Massimo Matteo Perf Venetian Driver

Brand Name: Massimo Matteo
Product Name: Perf Venetian Driver
Gender: Women's
Color: Amarelo Nubuck
Price: $41.85MSRP: $59.00

Massimo Matteo - Perf Venetian Driver. Color Blue Nubuck. Low Stock. On sale for $44.21. MSRP $59.00.. 3.7 out of 5 stars

Low Stock

Massimo Matteo Perf Venetian Driver

Massimo Matteo Perf Venetian Driver

Brand Name: Massimo Matteo
Product Name: Perf Venetian Driver
Gender: Women's
Color: Blue Nubuck
Price: $44.21MSRP: $59.00

Massimo Matteo - Woven Strap Driver. Color Elba Blue. Low Stock. On sale for $44.24. MSRP $79.00.. 5.0 out of 5 stars

Low Stock

Massimo Matteo Woven Strap Driver

Massimo Matteo Woven Strap Driver

Brand Name: Massimo Matteo
Product Name: Woven Strap Driver
Gender: Men's
Color: Elba Blue
Price: $44.24MSRP: $79.00

Massimo Matteo - Penny Keeper. Color Flame Red Nubuck. On sale for $38.90. MSRP $59.00.. 3.9 out of 5 stars

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Flame Red Nubuck
Price: $38.90MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Tan Bison. Low Stock. On sale for $44.21. MSRP $59.00.. 3.9 out of 5 stars

Low Stock

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Tan Bison
Price: $44.21MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Blue Nubuck. Low Stock. On sale for $37.13. MSRP $59.00.. 3.9 out of 5 stars

Low Stock

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Blue Nubuck
Price: $37.13MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Hot Pink Nubuck. Low Stock. On sale for $43.62. MSRP $59.00.. 3.9 out of 5 stars

Low Stock

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Hot Pink Nubuck
Price: $43.62MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Black Bison. On sale for $38.90. MSRP $59.00.. 3.9 out of 5 stars

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Black Bison
Price: $38.90MSRP: $59.00

Massimo Matteo - Penny Keeper. Color Black Nubuck. On sale for $44.25. MSRP $59.00.. 3.9 out of 5 stars

Massimo Matteo Penny Keeper

Massimo Matteo Penny Keeper

Brand Name: Massimo Matteo
Product Name: Penny Keeper
Gender: Women's
Color: Black Nubuck
Price: $44.25MSRP: $59.00

Massimo Matteo - Suede Penny Driver. Color Vinho. Low Stock. On sale for $44.16. MSRP $69.00.. 3.9 out of 5 stars

Low Stock

Massimo Matteo Suede Penny Driver

Massimo Matteo Suede Penny Driver

Brand Name: Massimo Matteo
Product Name: Suede Penny Driver
Gender: Men's
Color: Vinho
Price: $44.16MSRP: $69.00

Massimo Matteo - Driver With Bit. Color Cognac Pitstop w/ Bit. Low Stock. On sale for $46.92. MSRP $69.00.. 4.2 out of 5 stars

Low Stock

Massimo Matteo Driver With Bit

Massimo Matteo Driver With Bit

Brand Name: Massimo Matteo
Product Name: Driver With Bit
Gender: Men's
Color: Cognac Pitstop w/ Bit
Price: $46.92MSRP: $69.00

Massimo Matteo - Driver with Polished Bit. Color Cafe Nubuck. Low Stock. On sale for $28.26. MSRP $69.00.. 1.5 out of 5 stars

Low Stock

Massimo Matteo Driver with Polished Bit

Massimo Matteo Driver with Polished Bit

Brand Name: Massimo Matteo
Product Name: Driver with Polished Bit
Gender: Women's
Color: Cafe Nubuck
Price: $28.26MSRP: $69.00

Massimo Matteo - Venetian Driver. Color Marinho Nubuck. On sale for $39.65. MSRP $65.00.. 4.3 out of 5 stars

Massimo Matteo Venetian Driver

Massimo Matteo Venetian Driver

Brand Name: Massimo Matteo
Product Name: Venetian Driver
Gender: Men's
Color: Marinho Nubuck
Price: $39.65MSRP: $65.00

Massimo Matteo - Venetian Driver. Color Black. Low Stock. On sale for $48.75. MSRP $65.00.. 4.3 out of 5 stars

Low Stock

Massimo Matteo Venetian Driver

Massimo Matteo Venetian Driver

Brand Name: Massimo Matteo
Product Name: Venetian Driver
Gender: Men's
Color: Black
Price: $48.75MSRP: $65.00

Massimo Matteo - Venetian Driver. Color Cafe. Low Stock. On sale for $46.80. MSRP $65.00.. 4.3 out of 5 stars

Low Stock

Massimo Matteo Venetian Driver

Massimo Matteo Venetian Driver

Brand Name: Massimo Matteo
Product Name: Venetian Driver
Gender: Men's
Color: Cafe
Price: $46.80MSRP: $65.00

Massimo Matteo - Leather Saddle Driver. Color Black. Low Stock. On sale for $34.71. MSRP $89.00.. 1.0 out of 5 stars

Low Stock

Massimo Matteo Leather Saddle Driver

Massimo Matteo Leather Saddle Driver

Brand Name: Massimo Matteo
Product Name: Leather Saddle Driver
Gender: Men's
Color: Black
Price: $34.71MSRP: $89.00

Massimo Matteo - Natural Fiber Venetian. Color Marinho/Elba. Low Stock. On sale for $42.66. MSRP $79.00.. 4.3 out of 5 stars

Low Stock

Massimo Matteo Natural Fiber Venetian

Massimo Matteo Natural Fiber Venetian

Brand Name: Massimo Matteo
Product Name: Natural Fiber Venetian
Gender: Men's
Color: Marinho/Elba
Price: $42.66MSRP: $79.00

Massimo Matteo - Natural Fiber Venetian. Color Natural/Cafe. Low Stock. On sale for $41.87. MSRP $79.00.. 4.3 out of 5 stars

Low Stock

Massimo Matteo Natural Fiber Venetian

Massimo Matteo Natural Fiber Venetian

Brand Name: Massimo Matteo
Product Name: Natural Fiber Venetian
Gender: Men's
Color: Natural/Cafe
Price: $41.87MSRP: $79.00

Massimo Matteo - Pitstop Penny Driver. Color Black. On sale for $44.25. MSRP $59.00.. 4.3 out of 5 stars

Massimo Matteo Pitstop Penny Driver

Massimo Matteo Pitstop Penny Driver

Brand Name: Massimo Matteo
Product Name: Pitstop Penny Driver
Gender: Men's
Color: Black
Price: $44.25MSRP: $59.00

Massimo Matteo - Pitstop Penny Driver. Color Brown. On sale for $40.71. MSRP $59.00.. 4.3 out of 5 stars

Massimo Matteo Pitstop Penny Driver

Massimo Matteo Pitstop Penny Driver

Brand Name: Massimo Matteo
Product Name: Pitstop Penny Driver
Gender: Men's
Color: Brown
Price: $40.71MSRP: $59.00

Massimo Matteo - Venetian Driver. Color Whiskey. On sale for $48.75. MSRP $65.00.. 4.3 out of 5 stars

Massimo Matteo Venetian Driver

Massimo Matteo Venetian Driver

Brand Name: Massimo Matteo
Product Name: Venetian Driver
Gender: Men's
Color: Whiskey
Price: $48.75MSRP: $65.00

Massimo Matteo - Suede Penny Driver. Color Verde. Low Stock. On sale for $40.67. MSRP $59.00.. 4.0 out of 5 stars

Low Stock

Massimo Matteo Suede Penny Driver

Massimo Matteo Suede Penny Driver

Brand Name: Massimo Matteo
Product Name: Suede Penny Driver
Gender: Women's
Color: Verde
Price: $40.67MSRP: $59.00

Massimo Matteo - Suede Penny Driver. Color Tango. Low Stock. On sale for $46.76. MSRP $65.00.. 4.0 out of 5 stars

Low Stock

Massimo Matteo Suede Penny Driver

Massimo Matteo Suede Penny Driver

Brand Name: Massimo Matteo
Product Name: Suede Penny Driver
Gender: Women's
Color: Tango
Price: $46.76MSRP: $65.00