You're in Men's Shoes

Need a Personal Shopper?

Subscribe to
Bizrate emails for the hottest
deals & products
,
PLUS a chance to

WIN $25

sign me up!

New winners chosen weekly.
No purchase necessary.

Massimo Matteo Massimo Matteo Leather Penny Loafer

Massimo Matteo Massimo Matteo Leather Penny Loafer

Massimo Matteo Leather Penny Loafer

$179.99

$295.00 $179.99

Free shipping

at Bluefly

Best Seller
Massimo Matteo Penny Loafer 19

Massimo Matteo Penny Loafer 19

Nothing says business casual like a classic penny loafer. Where fun and style meet. This penny loafer flaunts a premium leather upper. Comfortable slip-on wear.Specially placed elastic on the collar.Classic round toe.Breathable leather lining and... ... more

Massimo Matteo Penny Loafer 19

Nothing says business casual like a classic penny loafer. Where fun and style meet. This penny loafer flaunts a premium leather upper. Comfortable slip-on wear.Specially placed elastic on the collar.Classic round toe.Breathable leather lining and...

$190.00

FREE shipping

go to store
Massimo Matteo New Penny Classic

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product... ... more

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product...

$98.00

FREE shipping

go to store
Best Seller
Massimo Matteo New Penny Classic

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product... ... more

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product...

$98.00

FREE shipping

go to store
Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio. ... more

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio.

Macy's

$325.00 $161.93

FREE shipping

go to store
Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio. ... more

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio.

Macy's

$325.00 $161.93

FREE shipping

go to store
Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio. ... more

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio.

Macy's

$325.00 $161.93

FREE shipping

go to store
matteo massimo&milano Shoes | Boots | Color: Black | Size: 10.5

matteo massimo&milano Shoes | Boots | Color: Black | Size: 10.5

Ostrich And Alligator ... more

$60.00

go to store
massimo matteo Shoes | Boat Shoe | Color: Brown | Size: 10

massimo matteo Shoes | Boat Shoe | Color: Brown | Size: 10

Brown Suede Boat Show, Size 10 ... more

$90.00

go to store
Men's Scandia Woods Leather Penny Loafers, Denim, Size 13

Men's Scandia Woods Leather Penny Loafers, Denim, Size 13

Free Shipping No Min. Ends 11/20. Use B3BCQ

Shoes by Scandia Woods. Comes in Denim Blue, Size 13 M. As popular and versatile today as they were when two pennies were all you needed to use a pay phone - and just as great a value! The genuine leather upper has perforated vamps, a unique design for... ... more

Men's Scandia Woods Leather Penny Loafers, Denim, Size 13

Shoes by Scandia Woods. Comes in Denim Blue, Size 13 M. As popular and versatile today as they were when two pennies were all you needed to use a pay phone - and just as great a value! The genuine leather upper has perforated vamps, a unique design for...

$49.99 $29.97

go to store
3-eye Chukka - Brown - Massimo Matteo Boots

3-eye Chukka - Brown - Massimo Matteo Boots

Massimo Matteo 3-eye Chukka - Complete your look with this distinguished Chukka! Upper made of smooth genuine leather featuring stitching detail at seams. Triple-eyelet lace construction. Plain round toe on a chukka boot silhouette. Leather lining and... ... more

3-eye Chukka - Brown - Massimo Matteo Boots

Massimo Matteo 3-eye Chukka - Complete your look with this distinguished Chukka! Upper made of smooth genuine leather featuring stitching detail at seams. Triple-eyelet lace construction. Plain round toe on a chukka boot silhouette. Leather lining and...

Lyst

$165.00 $116.00

FREE shipping

go to store
7-eye Wing Boot - Brown - Massimo Matteo Boots

7-eye Wing Boot - Brown - Massimo Matteo Boots

Massimo Matteo 7-eye Wing Boot - Feel like the dapper gentleman with the 7-Eye Wing Boot. Premium leather upper. Seven-eye lace closure. Soft leather lining. Lightly padded footbed. Leather outsole. Made in Italy. Measurements: Heel Height: 1 in... ... more

7-eye Wing Boot - Brown - Massimo Matteo Boots

Massimo Matteo 7-eye Wing Boot - Feel like the dapper gentleman with the 7-Eye Wing Boot. Premium leather upper. Seven-eye lace closure. Soft leather lining. Lightly padded footbed. Leather outsole. Made in Italy. Measurements: Heel Height: 1 in...

Lyst

$199.00 $119.00

FREE shipping

go to store
Men's Scandia Woods Leather Penny Loafers, Tan, Size 9.5 Wide Width

Men's Scandia Woods Leather Penny Loafers, Tan, Size 9.5 Wide Width

Free Shipping No Min. Ends 11/20. Use B3BCQ

Shoes by Scandia Woods. Comes in Tan, Size 9. 5 W. As popular and versatile today as they were when two pennies were all you needed to use a pay phone - and just as great a value! The genuine leather upper has perforated vamps, a unique design for... ... more

Men's Scandia Woods Leather Penny Loafers, Tan, Size 9.5 Wide Width

Shoes by Scandia Woods. Comes in Tan, Size 9. 5 W. As popular and versatile today as they were when two pennies were all you needed to use a pay phone - and just as great a value! The genuine leather upper has perforated vamps, a unique design for...

$49.99 $29.97

go to store
Men's Nunn Bush Penny Loafer, Red, Size 9.5

Men's Nunn Bush Penny Loafer, Red, Size 9.5

Free Shipping No Min. Ends 11/20. Use B3BCQ

Shoes by Nunn Bush. Comes in Burgundy, Size 9. 5 M. The one shoe that never goes out of style, in genuine hand-sewn leather. Fully cushioned footbed and smooth leather lining. Nonskid rubber sole. Import. Material: Leather. Nunn Bush Penny Loafer - The... ... more

Men's Nunn Bush Penny Loafer, Red, Size 9.5

Shoes by Nunn Bush. Comes in Burgundy, Size 9. 5 M. The one shoe that never goes out of style, in genuine hand-sewn leather. Fully cushioned footbed and smooth leather lining. Nonskid rubber sole. Import. Material: Leather. Nunn Bush Penny Loafer - The...

$79.99

go to store
Slip-on Wing Bit - Black - Massimo Matteo Slip-ons

Slip-on Wing Bit - Black - Massimo Matteo Slip-ons

Massimo Matteo Slip-on Wing Bit - Make a lasting impression with the detail-rich Massimo Matteo Slip-On Wing Bit loafer. Leather upper features perforated detailing. Slip-on entry. Square-toe construction. Wingtip design. Mixed leather and metal bit... ... more

Slip-on Wing Bit - Black - Massimo Matteo Slip-ons

Massimo Matteo Slip-on Wing Bit - Make a lasting impression with the detail-rich Massimo Matteo Slip-On Wing Bit loafer. Leather upper features perforated detailing. Slip-on entry. Square-toe construction. Wingtip design. Mixed leather and metal bit...

Lyst

$165.00 $99.00

FREE shipping

go to store
Men's Leather Slip On Penny Loafer Shoes - Lands' End - Black - 8H

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Black - 8H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even... ... more

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Black - 8H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even...

Lands' End

$99.95

FREE shipping

go to store
Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 9H

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 9H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even... ... more

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 9H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even...

Lands' End

$99.95

FREE shipping

go to store
Massimo Shoes | Brown Men Short Boots Massimo Emporio | Color: Brown | Size: 9.5

Massimo Shoes | Brown Men Short Boots Massimo Emporio | Color: Brown | Size: 9.5

Brown Leather Men Boots. Worn About Once Or Twice, In Good Condition. Brown Laces. Comes With Box. ... more

Massimo Shoes | Brown Men Short Boots Massimo Emporio | Color: Brown | Size: 9.5

Brown Leather Men Boots. Worn About Once Or Twice, In Good Condition. Brown Laces. Comes With Box.

Poshmark, Inc.

$150.00

go to store
Joseph Abboud Massimo Dress Lace Ups Men's Shoes

Joseph Abboud Massimo Dress Lace Ups Men's Shoes

Beautiful and unique, these fine dress shoes feature a smooth one-piece upper with brogued, wingtip styling. Leather upper fully lined. Long-lasting outsole. Spot clean. Genuine leather. Imported. Joseph Abboud Massimo Dress Lace Ups ... more

Joseph Abboud Massimo Dress Lace Ups Men's Shoes

Beautiful and unique, these fine dress shoes feature a smooth one-piece upper with brogued, wingtip styling. Leather upper fully lined. Long-lasting outsole. Spot clean. Genuine leather. Imported. Joseph Abboud Massimo Dress Lace Ups

Jos. A. Bank

$150.00 $109.00

FREE shipping

go to store
Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 10H

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 10H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even... ... more

Men's Leather Slip On Penny Loafer Shoes - Lands' End - Brown - 10H

If you value versatility as well as comfort, it's tough to top our penny loafer. It goes as well with slacks and a tie as it does with jeans. It's got a quality leather upper with a super comfy foam footbed. The rubber outsole adds grip. It's even...

Lands' End

$99.95

FREE shipping

go to store
Antonio Maurizi Leather Penny Loafer Black 44.5at Nordstrom Rack - Mens Shoes & Footwear - Loafers &

Antonio Maurizi Leather Penny Loafer Black 44.5at Nordstrom Rack - Mens Shoes & Footwear - Loafers &

45-Day Returns & Free Shipping on Orders Over $100

Reference size chart for European conversion. Almond moc toe. Topstitching detail. Leather construction. Split vamp strap. Slip-on style. Cushioned footbed. Low stacked heel. Made in Italy ... more

Antonio Maurizi Leather Penny Loafer Black 44.5at Nordstrom Rack - Mens Shoes & Footwear - Loafers &

Reference size chart for European conversion. Almond moc toe. Topstitching detail. Leather construction. Split vamp strap. Slip-on style. Cushioned footbed. Low stacked heel. Made in Italy

$475.00 $189.97

go to store
The Novak Suede Penny Loafer

The Novak Suede Penny Loafer

45-Day Returns & Free Shipping on Orders Over $100

Sizing: True to size. Round toe. Suede leather construction. Penny slot strap. Notched vamp. Zigzag trim on tongue. Slip-on style. Cushioned footbed. Topstitched midsole. Imported ... more

The Novak Suede Penny Loafer

Sizing: True to size. Round toe. Suede leather construction. Penny slot strap. Notched vamp. Zigzag trim on tongue. Slip-on style. Cushioned footbed. Topstitched midsole. Imported

$349.00 $69.97

go to store
Sandro Moscoloni 'Bimini' Penny Loafer (Men) Brown 7.5D at Nordstrom Rack - Mens Shoes & Footwear -

Sandro Moscoloni 'Bimini' Penny Loafer (Men) Brown 7.5D at Nordstrom Rack - Mens Shoes & Footwear -

45-Day Returns & Free Shipping on Orders Over $100

Rich contrast stitching marks a handsome penny loafer formed from rich vegetable-tanned leather.Sizing: True to size. D=standard width. Moc toe. Slit vamp strap. Leather construction. Contrast topstitching. Slip-on. Grip sole. Imported ... more

Sandro Moscoloni 'Bimini' Penny Loafer (Men) Brown 7.5D at Nordstrom Rack - Mens Shoes & Footwear -

Rich contrast stitching marks a handsome penny loafer formed from rich vegetable-tanned leather.Sizing: True to size. D=standard width. Moc toe. Slit vamp strap. Leather construction. Contrast topstitching. Slip-on. Grip sole. Imported

$140.00 $52.48

go to store
Zanzara Muse Brown Penny Loafers

Zanzara Muse Brown Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible. ... more

Zanzara Muse Brown Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible.

Men's Wearhouse

$129.99 $90.99

go to store
Joseph Abboud Clarence Penny Loafers Men's Shoes

Joseph Abboud Clarence Penny Loafers Men's Shoes

These Joseph Abboud penny loafers feature smooth, polished fine Italian leather uppers. Leather linings and cushioned footbed. Full rubber outsoles for long lasting comfort. 100 leather. Spot clean. Imported. Joseph Abboud Clarence Penny Loafers ... more

Joseph Abboud Clarence Penny Loafers Men's Shoes

These Joseph Abboud penny loafers feature smooth, polished fine Italian leather uppers. Leather linings and cushioned footbed. Full rubber outsoles for long lasting comfort. 100 leather. Spot clean. Imported. Joseph Abboud Clarence Penny Loafers

Jos. A. Bank

$165.00 $129.00

FREE shipping

go to store
Zanzara Muse Black Penny Loafers

Zanzara Muse Black Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible. ... more

Zanzara Muse Black Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible.

Men's Wearhouse

$129.99 $90.99

go to store
Zanzara Muse Brown Penny Loafers

Zanzara Muse Brown Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible. ... more

Zanzara Muse Brown Penny Loafers

The classic penny loafers receive an updated new look with a soft pebble leather detailing and apron-toe design. They have manmade outsoles that are durable and flexible.

Men's Wearhouse

$129.99 $90.99

go to store
Massimo Matteo New Penny Classic

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product... ... more

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product...

$98.00

FREE shipping

go to store
Massimo Matteo New Penny Classic

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product... ... more

Massimo Matteo New Penny Classic

Embrace modern sophistication in the Massimo Matteo New Penny Classic loafer. Leather upper.Slip-on construction.Moc toe design.Penny keeper detail at vamp.Leather lining and footbed.Stacked heel.Leather and rubber outsole.Made in Brazil.Product...

$98.00

FREE shipping

go to store
Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio. ... more

Massimo Emporio Men's Oxigen Suede Penny Loafers - Grey

Soft and supple suede styles these classic moc-toed penny loafers from Massimo Emporio.

Macy's

$325.00 $161.93

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Cognac

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store
Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather. ... more

Massimo Emporio Men's Giamo Loafers, Created for Macy's - Black

Massimo Emporio completes your suave and polished look with the sleek styling of these classic apron-toe loafers in rich and supple leather.

Macy's

$250.00

FREE shipping

go to store