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| Best Seller  | Richee Two-tone lugged Penny Loafer Men's VINNY'S Richee Two-tone lugged Penny Loafer - Black - Loafers A pop of contrast emboldens the top of a penny loafer crafted from Italian leather and grounded smartly on a lugged rubber sole. Leather or leather and genuine calf-hair upper/leather... more | FREE shipping go to store |
 | Men's VINNY'S Richee Leather Penny Loafers - Brown Vinny's collections are designed for the modern man’s everyday wardrobe, so it’s unsurprising that the roster includes a refined loafer. The Richee style in polished brown nappa leather features... more | FREE shipping go to store |
| Best Seller  | Men's Børn Taylor Penny Loafer - Brown - Loafers A high-traction contrast sole grounds a versatile loafer built from full-grain leather using Opanka hand construction for flexibility. more | FREE shipping go to store |
 | Men's Church's Penny-slot Leather Loafers - Brown Penny-slot leather loafers from CHURCH'S featuring wine red, calf leather, penny slot, round toe, slip-on style, branded insole and low heel. more | $953.00 $600.39 FREE shipping go to store |
 | Men's Donald J Pliner Calfskin Driver Penny Loafers - Brown Donald J Pliner calf leather driver penny loafers 0.50 in / 15 mm flat heel Round moc toe Notched vamp with keeper strap Slipon style Leather lining Rubber outsole Slipon style Made in Italy more | FREE shipping go to store |
 | Penny Loafer With Gancini Ornament Men's Ferragamo Penny Loafer With Gancini Ornament - White - Loafers Retro look Penny loafer with a high-shine brushed calfskin leather upper. The lines are squared at the toe, with a ruched stitching around the vamp to echo a classic feel. A slim... more | $950.00 $571.00 FREE shipping go to store |
 | Women's Sperry Top-Sider Seaport Penny Loafer - Gray - Loafers An iconic loafer with a classic keeper strap is fitted with a memory-foam footbed for ultimate comfort, enhanced by a hidden EVA midsole. The Traditional rubber outsole is updated with... more | FREE shipping go to store |
 | Men's HUGO Black Penny Trim Loafers Buffed leather loafers in black. more | $220.00 $147.00 go to store |
 | Men's Sandro Moscoloni Natal Penny Loafer - White - Loafers Introduce effortless elegance to your footwear collection with a timeless penny loafer crafted from buttery-soft leather and cushioned with a removable insole. Removable insole Leather... more | FREE shipping go to store |
 | Men's Bruno Magli Silas Penny Loafer - Brown - Loafers Sharp contrast stitching touches up a handsome Italian loafer with a smart, durable sole. Leather upper and lining/rubber sole Made in Italy Men's Shoes. more | $298.00 $249.99 FREE shipping go to store |
 | Men's Santoni Black Leather Penny Loafers Hand-polished grained leather loafers in black. more | $705.00 $494.00 FREE shipping go to store |
 | Brown Calf Suede Varsity Penny Loafers Men's Thom Browne Brown Calf Suede Varsity Penny Loafers - Black Calfskin suede loafers in brown. more | FREE shipping go to store |
 | Men's Rockport Maverick Penny Loafer - Brown - Loafers Get the comfort and flexibility you need with this lugged-sole penny loafer that will keep you moving throughout your day with ease. more | FREE shipping go to store |
 | Handsewn Leather Penny Loafers Men's Peter Millar Handsewn Leather Penny Loafers - Brown Peter Millar penny loafers in luxurious leather with a rich matte finish Chunky heel Handstitched round moc toe Penny keeper strap Innovative foam insole Sheepskin lining Welted sole... more | FREE shipping go to store |
 | Women's Jack Rogers Meyers Moc Toe Penny Loafer - Red - Loafers Minimalist design showcases the rich suede of this timeless penny loafer with moc-toe stitching and a flexible, lightweight frame. more | FREE shipping go to store |
 | Gommino Round Toe Penny Loafers Men's Tod's Gommino Round Toe Penny Loafers - Brown 100% Calf Leather, 100% Rubber, 100% Calf Suede. Made in Italy. more | $602.47 $475.96 FREE shipping go to store |
 | Wakith Suede Apron Toe Penny Loafer Men's ALDO Wakith Suede Apron Toe Penny Loafer - Brown - Loafers Classic and versatile, this loafer made of brushed suede features a contoured penny strap and classic apron toe for a smart, streamlined look. more | FREE shipping go to store |
 | Men's G.H.BASS Larson Leather Penny Loafer - Brown - Loafers This classic penny loafer boasts handsome moc-stitching and classic beefroll details that pair equally well with crisp suits and casual shorts. more | FREE shipping go to store |
 | Men's Johnston & Murphy Athens Penny Driving Loafer - Blue - Loafers Sleek and sporty, this loafer made of Brazilian leather features a classic penny strap and foam cushioning set atop a lugged driver sole that wraps up the heel. Removable memory foam... more | FREE shipping go to store |
 | Men's Tricker's James Penny Loafers - Black 100% Leather. Made in United Kingdom. more | $673.95 $609.65 FREE shipping go to store |
 | Men's VINNY'S Yardee Penny Loafer - Brown - Loafers A crepe rubber sole grounds this rich suede penny loafer fashioned with a cushioned footbed for daylong comfort. Cushioned footbed Leather upper and lining/rubber sole Made in Portugal Black... more | $270.00 $148.50 FREE shipping go to store |
 | Men's Paul Stuart Garret Penny Loafer - Purple - Loafers Elevate your formal staples with this Italian-made leather loafer built on a crisp stacked heel and embellished with a classic penny keeper strap. Leather upper, lining and sole Made in Italy. more | FREE shipping go to store |
 | Croftwood Check Leather Penny Loafer Men's Burberry Croftwood Check Leather Penny Loafer - Black - Loafers Burberry's iconic check framed in apron-toe stitching lets you go bold and distinctive in a penny loafer that's crafted smartly from polished Italian leather. Leather upper, lining... more | $790.00 $474.00 FREE shipping go to store |
 | Bateau Water Resistant Penny Loafer Men's J.M. Weston Bateau Water Resistant Penny Loafer - Blue - Loafers Inspired by classic boat shoes, this loafer made of water-resistant leather features bright stitching that matches the grippy sole for a smart, prepster look. Water-resistant... more | FREE shipping go to store |
 | Men's Stuart Weitzman Sw Club La Penny Loafer Men's - Black - Loafers The SW CLUB LA PENNY LOAFER features a unique mixed-material design that pairs a leather upper with stretch panels in a nod to our signature brand code. It is crafted by our artisans... more | FREE shipping go to store |
 | Men's VINNY'S Townee Penny Loafer - Black - Loafers A classic penny keeper and moc toe lend timeless sophistication to a versatile loafer rendered in polished leather. Cushioned footbed Leather upper and lining/rubber sole Made in Portugal Black... more | FREE shipping go to store |
 | Men's Mezlan Solomeo Penny Loafer - Brown - Loafers A woven upper and geometric penny keeper add modern elements to a sophisticated leather loafer featuring a slender moc toe. Cushioned footbed Leather upper, lining and sole Made in Spain. more | FREE shipping go to store |
 | Randolph Leather Penny Loafers Men's Allen Edmonds Randolph Leather Penny Loafers - Brown Allen Edmonds "Randolph" loafer in smooth leather Stacked heel Apron toe Notched vamp Penny keeper strap Slipon style Lining: Leather Made in USA more | FREE shipping go to store |
 | Randolph Leather Penny Loafers Men's Allen Edmonds Randolph Leather Penny Loafers - Brown Allen Edmonds "Randolph" penny loafers in smooth leather Stacked heel Round toe Silvertone bit strap Leather lining Slip-on style Made in USA. more | FREE shipping go to store |
 | Women's Sperry Top-Sider Seaport Penny Loafer - Brown - Loafers An iconic loafer with a classic keeper strap is fitted with a memory-foam footbed for ultimate comfort, enhanced by a hidden EVA midsole. The Traditional rubber outsole is updated with... more | FREE shipping go to store |
 | Men's John Lobb Thorne Penny Loafer - Black - Loafers Finely crafted in Italy from supple leather, this penny loafer is set on a rubber sole with a 'Rasp' tread, an homage to traditional tools used in shoemaking. Leather upper and lining/rubber sole... more | FREE shipping go to store |
 | Men's Santoni Carlos Penny Loafer - Brown - Loafers Richly grained suede brings supple flexibility to a timeless penny loafer masterfully crafted in Italy. Leather upper, lining and sole Made in Italy. more | FREE shipping go to store |
 | Men's Camper Walden Penny Loafer - Brown - Loafers A simple, classic design underscores the timeless appeal of a burnished leather penny loafer complete with comfort-enhancing OrthoLite® cushioning. more | FREE shipping go to store |
 | Men's Camper Walden Penny Loafer - Blue - Loafers A statement-making sole designed for optimal traction helps you take confident strides in this durable loafer outfitted with an OrthoLite® footbed. more | FREE shipping go to store |
 | Men's Thom Browne Black Varsity Penny Loafers Grosgrain loafers in black. Grained leather piping throughout. more | $950.00 $589.00 FREE shipping go to store |
 | Men's Christian Louboutin Penny Loafers - White 100% Calfskin. Made in Italy. more | $980.39 $735.29 FREE shipping go to store |
 | Men's Tod's Penny Loafer Sneaker - Blue - Loafers Keep your off-duty look polished with this suave Italian loafer crafted of velvety suede and set in a sporty bumper cupsole with signature nubby tread. Leather upper and lining/rubber sole Made in Italy... more | FREE shipping go to store |
 | Men's Tod's Suede Penny Loafers - Black Tods mens loafers. Shoe style: slip-on. Vamp style: penny loafers. Upper material: suede. Solematerial: rubber. Tods mens black suede penny loafers. Featuring exposed handmade stitching, stamped tods monogram,... more | $595.00 $300.00 FREE shipping go to store |
 | New Damon 1 Slip-on Penny Loafer Men's Geox New Damon 1 Slip-on Penny Loafer - Brown - Loafers A classic penny strap tips a handsome leather loafer into timeless territory, while Geox's signature perforated sole keeps your feet cool and dry. more | FREE shipping go to store |
 | Supersport Moc Toe Penny Loafer Men's Allen Edmonds Supersport Moc Toe Penny Loafer - Blue - Loafers This hand-sewn penny loafer offers complete comfort with contoured support, shock absorption and stability. more | FREE shipping go to store |
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