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| Best Seller  | Men's Cole Haan Modern Classics Penny Loafer - Brown - Loafers A traction-enhancing sole adds everyday utility to a classic penny loafer shaped from smooth, burnished leather. Traction-enhancing outsole with rubber pods Leather upper and lining/leather... more | FREE shipping go to store |
 | Men's Eastland Bristol Penny Loafer - Black - Loafers A classic penny keeper and glossy leather upper lend modern sophistication to a luxe loafer set on a cushioned footbed and slip-resistant sole. Memory foam cushioning Slip-resistant sole Leather... more | FREE shipping go to store |
| Best Seller  | Men's To Boot New York Zenith Penny Loafer - Brown - Loafers A woven upper and classic penny keeper create modern dimension on an Italian leather loafer grounded by a cushioned footbed for comfortable wear. Cushioned footbed with arch support Leather... more | FREE shipping go to store |
 | J. Crew Shoes | Jcrew Rowan Penny Loafers In Leather Item Bk482 | Color: Tan | Size: 6 Step Into Cooler Weather With A Chunky-Heeled Penny Loafer That Toes The Line Between Classic And Modern Perfectly. This Leather Was Sourced From A Tannery That's Certified By The Leather Working Group (Lwg), An Organization That Works To Promote... more | go to store |
 | J. Crew Shoes | J Crew Rowan Penny Loafers In Brown Leather | Color: Brown/Tan | Size: 6 Step Into Cooler Weather With A Chunky-Heeled Penny Loafer That Toes The Line Between Classic And Modern Perfectly. This Leather Was Sourced From A Tannery That's Certified By The Leather Working Group (Lwg), An Organization That Works To Promote... more | go to store |
 | J. Crew Shoes | J. Crew Rowan Penny Loafers In Leather And Calf Hair 9.5 | Color: Black | Size: 9.5 Step Into Cooler Weather With A Chunky-Heeled Penny Loafer That Perfectly Toes The Line Between Classic And Modern. Bonus: This Pair Is Made With Luxe Italian Calf Hair. Leather/Calf-Hair Upper. Leather Lining. Man-Made Sole. Item Bk483. Excellent... more | go to store |
 | Halie Slingback Moc Toe Loafer - Black - Donald J Pliner Flats Women's Donald J Pliner Halie Slingback Moc Toe Loafer - Black - Loafers A classic moc-toe penny loafer gets a modern update with a slingback strap and lightweight, lugged EVA-platform sole. 1 1/4" heel Memory foam cushioning Leather upper and... more | FREE shipping go to store |
 | Ellowyn Penny Loafer - Black - Clarks Flats Women's Clarks Ellowyn Penny Loafer - Black - Loafers Add to your casual or professional fits with the Ellowyn loafer from Clarks. The classic penny loafer look makes for versatile styling, while the cushy footbed and wedge sole ensure support... more | go to store |
 | Sync Collapsible Heel Penny Loafer Men's Dune Sync Collapsible Heel Penny Loafer - Brown - Loafers A penny keeper strap and apron toe lend classic sophistication to this crisp leather loafer outfitted with a collapsible heel for a versatile modern twist. Leather upper/textile... more | FREE shipping go to store |
 | Men's Bruno Magli Xane Driving Penny Loafer - Brown - Loafers Supple suede and a classic penny keeper create modern appeal on an Italian driving loafer that will complement your sophisticated wardrobe. Leather upper and lining/rubber sole Made in Italy more | FREE shipping go to store |
 | Cruise Knit Driver Penny Loafers Men's Peter Millar Cruise Knit Driver Penny Loafers - Blue Peter Millar "Cruise" classic meets modern designed polyester and nylon knit driver penny loafers. Breathable performance knit uppers, a machinewashable design and a timeless loafer shape offer... more | FREE shipping go to store |
 | Men's Stuart Weitzman Club Penny Loafer - Blue - Loafers Debossed logo detailing and a classic penny keeper add sophisticated elements to a luxe loafer designed with a squared-off moc toe for modern appeal. Leather upper, lining and sole Made in Italy more | FREE shipping go to store |
 | Men's Stuart Weitzman Club Penny Loafer - Brown - Loafers Debossed logo detailing and a classic penny keeper add sophisticated elements to a luxe loafer designed with a squared-off moc toe for modern appeal. Leather upper, lining and sole Made in Italy more | FREE shipping go to store |
 | Men's Bruno Magli Xane Driving Penny Loafer - Blue - Loafers Supple suede and a classic penny keeper create modern appeal on an Italian driving loafer that will complement your sophisticated wardrobe. Leather upper and lining/rubber sole Made in Italy more | FREE shipping go to store |
 | Men's Bruno Magli Xane Driving Penny Loafer - Brown - Loafers Woven leather and a classic penny keeper create modern appeal on an Italian driving loafer that will complement your sophisticated wardrobe. Leather upper and lining/rubber sole Made in Italy more | FREE shipping go to store |
 | Men's Eastland Bristol Penny Loafer - Black - Loafers A classic penny keeper and glossy leather upper lend modern sophistication to a luxe loafer set on a cushioned footbed and slip-resistant sole. Memory foam cushioning Slip-resistant sole Leather... more | FREE shipping go to store |
 | Men's Bruno Magli Xane Driving Penny Loafer - Brown - Loafers Supple suede and a classic penny keeper create modern appeal on an Italian driving loafer that will complement your sophisticated wardrobe. Leather upper and lining/rubber sole Made in Italy more | FREE shipping go to store |
 | Men's Hush Puppies Leo Penny Loafer - Yellow - Loafers The classic penny loafer gets a modern upgrade with the Leo. Featuring an unbelievably soft nubuck leather upper and a sleek two-toned midsole for a pair you can dress up or down with your whole... more | FREE shipping go to store |
 | Men's Hush Puppies Leo Penny Loafer - Brown - Loafers The classic penny loafer gets a modern upgrade with the Leo. Featuring an unbelievably soft nubuck leather upper and a sleek two-toned midsole for a pair you can dress up or down with your whole... more | FREE shipping go to store |
 | Men's Hush Puppies Leo Penny Loafer - Green - Loafers The classic penny loafer gets a modern upgrade with the Leo. Featuring an unbelievably soft nubuck leather upper and a sleek two-toned midsole for a pair you can dress up or down with your whole... more | FREE shipping go to store |
 | Men's Hush Puppies Leo Penny Loafer - Blue - Loafers The classic penny loafer gets a modern upgrade with the Leo. Featuring an unbelievably soft nubuck leather upper and a sleek two-toned midsole for a pair you can dress up or down with your whole... more | FREE shipping go to store |
 | Men's COACH Cooper Loafer - Black - Loafers Editors Notes: A modern twist on the classic style, these dress loafers for men are updated with an elevated platform and a penny keeper detailed with our Signature coin for an iconic Coach look Smooth... more | go to store |
 | Men's Ted Baker Parliament Loafer - Blue - Loafers Get going in the modern-classic look of the Ted Baker Parliament loafer. A supple leather and penny slot bring out the classy appeal of the round-toe loafer. Memory foam comfort footbed and flexible... more | FREE shipping go to store |
 | Men's Ted Baker Parliament Loafer - Brown - Loafers Get going in the modern-classic look of the Ted Baker Parliament loafer. A supple leather and penny slot bring out the classy appeal of the round-toe loafer. Memory foam comfort footbed and flexible... more | FREE shipping go to store |
 | Men's Ted Baker Parliament Loafer - Brown - Loafers Get going in the modern-classic look of the Ted Baker Parliament loafer. A supple leather and penny slot bring out the classy appeal of the round-toe loafer. Memory foam comfort footbed and flexible... more | FREE shipping go to store |
 | Sw Club Classic Penny Loafer Men's Men's Stuart Weitzman Sw Club Classic Penny Loafer Men's - Black - Loafers The SW CLUB CLASSIC PENNY LOAFER is timeless - not traditional. Modern polished lines define the look from its subtly protruding welt to its broader rounded square toe. Note its... more | FREE shipping go to store |
 | J. Crew Shoes | J. Crew Rowan Penny Loafers In Leather And Calf Hair* | Color: Black/Tan | Size: 5.5 Step Into Cooler Weather With A Chunky-Heeled Penny Loafer That Perfectly Toes The Line Between Classic And Modern. Bonus: This Pair Is Made With Luxe Italian Calf Hair. Leather/Calf-Hair Upper. Leather Lining. Man-Made Sole. Import. Select Stores.... more | go to store |
 | American Classics Pinch Penny Loafer Men's Cole Haan American Classics Pinch Penny Loafer - Black - Loafers A classic penny keeper details a sophisticated leather loafer grounded by a foam-cushioned footbed and lightweight sole for optimal comfort. Grand.OS energy-foam cushioning Leather... more | FREE shipping go to store |
 | American Classics Pinch Penny Loafer Men's Cole Haan American Classics Pinch Penny Loafer - Brown - Loafers A classic penny keeper details a sophisticated leather loafer grounded by a foam-cushioned footbed and lightweight sole for optimal comfort. Grand.OS energy-foam cushioning Leather... more | FREE shipping go to store |
 | American Classics Penny Loafer Men's Cole Haan American Classics Penny Loafer - Brown - Loafers Spruce up your smart casual look donning the American Classics penny loafer from Cole Haan. This timeless loafer flaunts a lightweight leather construction with EVA foam footbed and... more | $159.99 $129.98 FREE shipping go to store |
 | American Classics Penny Loafer Men's Cole Haan American Classics Penny Loafer - Brown - Loafers A classic penny keeper details a sophisticated loafer grounded by a foam-cushioned footbed and lightweight sole for optimal comfort. Cushioning: absorbs impact and distributes weight for... more | FREE shipping go to store |
 | Men's Stuart Weitzman Club Classic Penny Loafer - Brown - Loafers Classic and versatile, this loafer topped with a traditional penny strap features a softly squared apron toe and a smart, streamlined profile. Leather upper and lining/rubber sole Made... more | FREE shipping go to store |
 | Men's Rockport Classic Penny Loafer - Gray - Loafers A clean-cut silhouette defines a classic penny loafer fitted with ADIPRENE(R) by adidas cushioning for all-day comfort. Round toe Slip-on style Leather upper, manmade sole Imported more | $115.00 $79.95 FREE shipping go to store |
 | Classic Dan Leather Tassel Penny Loafers Women's Sebago Classic Dan Leather Tassel Penny Loafers - White Sebago "Dan" made of smooth corrected grain leather to stand the test of time and handsewn with the finest craftsmanship, these 4 seasons slip on beefroll penny loafer mocs come with upper... more | FREE shipping go to store |
 | Men's Thom Browne Brown Classic Penny Loafers - Black Buffed calfskin loafers in brown. more | $890.00 $516.00 go to store |
 | American Classics Penny Loafer Men's Cole Haan American Classics Penny Loafer - Natural - Loafers A classic penny keeper details a sophisticated loafer grounded by a foam-cushioned footbed and lightweight sole for optimal comfort. Cushioning: absorbs impact and distributes weight... more | FREE shipping go to store |
 | Gomma Classic Leather Penny Loafers Women's Tod's Gomma Classic Leather Penny Loafers - Brown Tod's classic penny loafers in smooth calf leather 0.75 in / 20 mm flat heel Round moc toe Notched vamp with keeper strap Slipon style Lining: Virgin wool Rubber outsole Made in Italy more | FREE shipping go to store |
 | Men's Sebago Classic Joe Penny Loafers - Black 100% Leather. Made in Mexico. more | $263.30 $203.66 go to store |
 | American Classics Pinch Penny Loafer Men's Cole Haan American Classics Pinch Penny Loafer - Brown - Loafers A classic penny keeper details a sophisticated leather loafer grounded by a foam-cushioned footbed and lightweight sole for optimal comfort. Grand.OS energy-foam cushioning Leather... more | FREE shipping go to store |
 | Men's Sebago Classic Joe Penny Loafers - Black 100% Leather. Made in Mexico. more | $246.49 $180.19 go to store |
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