Men's Shoes › wynston penny loafer

Motor Penny Driving Loafer

Men's Florsheim Motor Penny Driving Loafer - Brown - Loafers From professional meetings to a laid-back brunch settings, the Florsheim Motor Penny driving loafer is the right pick. Woven-textured upper with classic stitching details uplifts this leather... more

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

Moana Penny Loafer

Men's Rodd & Gunn Moana Penny Loafer - Brown - Loafers Smooth suede invigorates the look of a classic penny loafer grounded by a lightweight rubber sole. more

Penny Loafer

Men's Ferragamo Penny Loafer - White - Loafers Contemporary casual. Soft suede gentlemen's loafer with an elongated silhouette and slightly squared toe. Raised stitching across the instep adds texture to this sophisticated slip on. Flexible rubber... more

Natal Penny Loafer

Men's Sandro Moscoloni Natal Penny Loafer - Brown - 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

Ravello Penny Loafer

Men's To Boot New York Ravello Penny Loafer - Black - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... more

Penny Loafer

Men's Common Projects Penny Loafer - Black - Loafers Impeccable craftsmanship shines through on this Italian-crafted penny loafer done in burnished calfskin leather with foil-stamped style and production codes. Leather upper, lining and sole Made in... more

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

Taylor Penny Loafer

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

Penny-slot Leather Loafers

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

Calfskin Driver Penny Loafers

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

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

Seaport Penny Loafer

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

Natal Penny Loafer

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

Brown Calf Suede Varsity Penny Loafers

Men's Thom Browne Brown Calf Suede Varsity Penny Loafers - Black Calfskin suede loafers in brown. more

Maverick Penny Loafer

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

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. more

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

Meyers Moc Toe Penny Loafer

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

Athens Penny Driving Loafer

Men's Johnston & Murphy Athens Penny Driving Loafer - Brown - 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

Wakith Penny Loafer

Men's ALDO Wakith Penny Loafer - Blue - Loafers Perk up your laidback outfit with the Aldo Wakith loafer. Be it the timeless penny slot or the classy leather upper, you can never go wrong with this round-toe slip-on. Leather upper. Slip-on. Round moc... more

Logo Plaque Penny Loafers

Men's Dolce & Gabbana Logo Plaque Penny Loafers - White Dimensions: Heel: 1.5cm, Sole: 1cm. 100% Buckskin Leather. Made in Italy.. more

Gerry Penny Loafer

Men's Anthony Veer Gerry Penny Loafer - Black - Loafers Stay grounded in this supple leather pair of timeless dress shoes from Anthony Veer. The Gerry penny loafer is expertly designed with a stacked heel, recraftable leather outsole, and Goodyear welt... more

Adacter Penny Loafer

Men's Geox Adacter Penny Loafer - Gray - Loafers A supple suede upper and classic penny keeper lend luxe elements to a sophisticated loafer grounded by a cushioned footbed and durable sole. more

Huxley Suede Espadrille Penny Loafers

Men's Paul Stuart Huxley Suede Espadrille Penny Loafers - Natural Paul Stuart "Huxley" penny loafers in calf suede Braidedjute flat heel Round moc toe Suede penny keeper strap Leather lining Rubber crepe sole Slipon style Made in Portugal more

Thom E Penny Loafer Slingback Sandal At Nordstrom

Men's Thom Browne Thom E Penny Loafer Slingback Sandal At Nordstrom - Loafers Thom Browne continues to redefine wardrobe classics with this smooth leather slingback sandal boasting the cutout shell of a traditional penny loafer. Adjustable slingback... more

Tesoro Penny Loafer

Men's To Boot New York Tesoro Penny Loafer - Brown - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

Vinny’S ’S Townee Leather Penny Loafers

Men's VINNY'S Vinny’S ’S Townee Leather Penny Loafers - Black Known for its dress shoes crafting history, the Danish brand, Vinny, presents its interpretation of iconic Penny loafers. Made from polished leather, they feature soft footbeds that offer... more

Grand Laser Driving Penny Loafer

Men's Cole Haan Grand Laser Driving Penny Loafer - Brown - Loafers A generously padded cuff and footbed bring grand comfort to a leather driving shoe built to last on a flexible rubber sole that curves at the toe and heel. more

Raging Leather Penny Loafers

Men's Bruno Magli Raging Leather Penny Loafers - Black Bruno Magli "Raging" loafers in brushed Italian calf leather 1.25 in / 30 mm stacked heel Almond toe Penny keeper strap Leather lining Rubber outsole Item Weight (Lbs.): 3.0 Slipon style Item runs... more

Berkly Penny Loafer

Men's Dune Berkly Penny Loafer - Blue - Loafers Smooth suede composition and a moc toe make this penny loafer a perfect option for contemporary casual style. more

Luis Penny Loafer

Men's Kurt Geiger Luis Penny Loafer - Blue - Loafers A subtle penny keeper and moc toe add timeless sophistication to a versatile loafer rendered in rich leather. Cushioned footbed with arch support Leather upper, lining and sole Made in Portugal. more

Varsity Penny Loafer

Men's Thom Browne Varsity Penny Loafer - Loafers Supple calfskin leather throughout ensures comfort and flexibility as it also elevates this handsome Italian loafer with a bit of branding on the heel loop. Leather upper, lining and sole Made in Italy... more

Berkly Penny Loafer

Men's Dune Berkly Penny Loafer - Brown - Loafers Pull together your look with the effortlessly polished style of this contemporary take on a classic penny loafer. more

St.1 Hybrid Penny Loafer

Men's Ecco St.1 Hybrid Penny Loafer - Brown - Loafers ECCO FLUIDFORM tech brings an anatomical fit and more energy return, ensuring comfort in this easy-on leather loafer. Advanced SHOCK THRU point provides shock absorption, resulting in a feel that's... more

Rucci Penny Loafer

Men's Florsheim Rucci Penny Loafer - Brown - Loafers Add flair to your smart look with the Rucci penny loafer from Florsheim. Crafted from rich leather, this slip-on seamlessly blends elegance with timeless style. With its fully cushioned insole and... more

Richee Penny Loafer

Men's VINNY'S Richee Penny Loafer - Brown - Loafers Both streamlined and substantial, this classic leather penny loafer pairs a simple apron toe with a slightly chunky rubber sole grounding every step. more

Leather Penny Loafers

Men's Allen Edmonds Leather Penny Loafers - Brown Allen Edmonds penny loafers in smooth leather Handsewn construction Flat heel Round moc toe Penny keeper strap Leather lining Flexible rubber tread sole Slipon style Imported more