Men's Shoes › Leather › gerry penny loafer

Taylor Moc Toe Penny Loafer

Men's Johnston & Murphy Taylor Moc Toe Penny Loafer - Brown - Loafers A water-resistant penny loafer crafted from Italian leather and set on contoured cushioning offers lasting style and comfort. Cushioned footbed with arch support Water-resistant... more

Larson Leather Penny Loafer

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. Leather upper, lining and sole Imported more

Spherica Penny Loafer

Men's Geox Spherica Penny Loafer - Black - Loafers A classic penny keeper brings sophistication to this leather loafer that's incredibly light and breathable with a durable, signature tech sole. Removable, cushioned insole with arch support Patented... more

Newman Penny Loafer

Men's Allen Edmonds Newman Penny Loafer - Brown - Loafers A classic penny keeper and antique finish lend timeless sophistication to a leather loafer that will elevate your desk-to-dinner style. Non-removable cushioned insole with arch support Leather... more

Platform Penny Loafer

Men's Rag & Bone Platform Penny Loafer - Natural - Loafers A scalloped tongue and lugged platform sole lend unexpected dimension to a suede penny loafer kept comfortable with an OrthoLite® insole. OrthoLite insole Leather upper and lining/synthetic... more

Taylor Moc Toe Penny Loafer

Men's Sandro Moscoloni Taylor Moc Toe Penny Loafer - Brown - Loafers Elevate your fit with a moc-toe penny loafer crafted from burnished leather with a cushioned footbed and flexible rubber sole. Cushioned EVA footbed with arch support Leather upper... more

Medusa Coin Penny Driving Loafer

Men's Versace Medusa Coin Penny Driving Loafer - Natural - Loafers Set on a segmented driver sole with Greek-key tread, this calfskin-suede loafer features a Medusa-head 'coin' inserted in the keeper strap. Removable insole Leather upper and... more

Ron Haydon Weatherproof Penny Loafer

Men's Ron White Ron Haydon Weatherproof Penny Loafer - Brown - Loafers A classic penny keeper and supple suede upper lend timeless sophistication to a luxe loafer grounded by a cushioned footbed and slip-resistant lug sole. Multilayered,... more

Burke Penny Loafer

Men's Stacy Adams Burke Penny Loafer - Black - Loafers A slim penny keeper and moc toe add timeless elements to a sophisticated loafer set on a cushioned insole for comfortable wear. Removable, cushioned insole with arch support Leather upper/textile... more

Raging Penny Loafer

Men's Bruno Magli Raging Penny Loafer - Brown - Loafers A full-length rubber sole and leather lining enhance the overall comfort of this Italian-crafted penny loafer. Leather upper and lining/rubber sole Made in Italy more

Crosta Penny Loafer

Men's Christian Louboutin Crosta Penny Loafer - White - Loafers A logo-engraved disc shaped like a classic coin is inserted into the penny slot of a richly grained suede loafer trimmed with a scalloped tongue. The iconic red sole—born from a fateful... more

Payton Penny Loafer

Men's Bruno Magli Payton Penny Loafer - Brown - Loafers A lightly cushioned footbed brings impeccable comfort to a smooth loafer crafted from smooth Italian leather. Leather upper and lining/rubber sole Made in Italy more

Metropole London Penny Loafer

Men's Ecco Metropole London Penny Loafer - Black - Loafers Signature comfort details bring everyday appeal to a timeless penny loafer shaped from smooth, burnished leather. Removable dual-fit insole for wider fit and roomier toe area ECCO FLUIDFORM... more

Mocassino Gomma Penny Loafer

Men's Tod's Mocassino Gomma Penny Loafer - Blue - Loafers A classic keeper strap adds a refined flourish to a sharp Italian loafer crafted in soft calfskin leather that's stamped at the side with the label's logo. Tod's signature pebbled sole adds... 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. Cushioning: absorbs impact and distributes weight for... more

Desio Gancio Ornament Penny Loafers

Men's Ferragamo Desio Gancio Ornament Penny Loafers - Black Ferragamo loafers in grained leather Stacked heel Apron toe Leather penny keeper strap with Gancio ornament Rubber outsole Lining: Goat leather/leather Slipon style Made in Italy more

Tevin Penny Loafer

Men's Thomas & Vine Tevin Penny Loafer - Black - Loafers Thomas & Vine Tevin Men s Loafer Live your best life in the Tevin men s Loafer from Thomas & Vine. With a recycled textile upper featuring leather accents, this penny Loafer supports your best... more

Pace Suede Penny Loafers

Men's John Lobb Pace Suede Penny Loafers - Green John Lobb "Pace" penny loafers in calf suede Flat heel Round moc toe Vamp with penny keeper stitching Leather lining Rubber outsole Slipon style Made in United Kingdom more

Stamped-Logo Leather Penny Loafers

Men's Tod's Stamped-Logo Leather Penny Loafers - Black Tod's loafers in smooth calf leather feature a stamped monogram on the tongue Stacked heel Round moc toe Leather penny keeper strap Engraved heel logo Rubber outsole with embossed rubber pebbles... more

Titouan Penny Loafer

Men's Mephisto Titouan Penny Loafer - Brown - Loafers A classic penny keeper and an apron toe lend timeless sophistication to a leather loafer that will elevate your polished style. Removable insole Leather upper and lining/rubber sole Made in Portugal more

Hamilton Penny Strap Driving Loafer

Men's Marc Joseph New York Hamilton Penny Strap Driving Loafer - Gray - Loafers A classic penny strap and stitched moc toe bring traditional detailing to a loafer set on plush cushioning and a driving sole made of grippy, segmented rubber. Removable,... more

Supersport Moc Toe Penny Loafer

Men's Allen Edmonds Supersport Moc Toe Penny Loafer - Brown - Loafers This hand-sewn penny loafer offers complete comfort with contoured support, shock absorption and stability. Memory foam cushioning Leather upper and lining/rubber sole Imported more

Ronny Penny Loafer

Men's To Boot New York Ronny Penny Loafer - Black - Loafers A traditional penny keeper and moc toe lend timeless sophistication to a supple suede loafer grounded by a cushioned footbed for long-lasting wear. Cushioned footbed with arch support Leather... 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

Harris Leather Penny Loafers

Men's Gianvito Rossi Harris Leather Penny Loafers - Black Upper: calf leather. Lining: leather. Sole: leather insole, rubber sole. Toe shape: round toe. Made in Italy. Includes: shoe box, dust bag. Designer color name: Moka. more

Logan Penny Loafer

Men's G.H.BASS Logan Penny Loafer - Brown - Loafers This hand-sewn suede penny loafer showcases handsome stitching and flat-strap styling for all-day, everyday sophistication. Arch support Leather upper, lining and sole Imported more

Patrick Penny Loafer

Men's Eastland Patrick Penny Loafer - Brown - Loafers Eastland Patrick Men's Penny Loafer Elevate your prep with the Eastland Patrick penny Loafer. Featuring a leather upper with a penny holder accent, this driving moc supports sans Socks. The insole... more

Sammy Two-Tone Penny Loafer

Men's AllSaints Sammy Two-Tone Penny Loafer - Black - Loafers Textural, threaded trim adds a subtle flourish to this two-tone penny loafer crafted from sleek leather for a look of classic sophistication. Removable insole Leather upper, lining and sole... more

Penny Loafers

Men's Thom Browne Penny Loafers - Black Offering a fresh take on classic attire, Thom Browne's avant-garde aesthetic runs throughout each collection – from tailoring with the signature four stripes to leather shoes with dressed-down accents. Crafted... more

Titouan Penny Loafer

Men's Mephisto Titouan Penny Loafer - Brown - Loafers A classic penny keeper and an apron toe lend timeless sophistication to a leather loafer that will elevate your polished style. Removable insole Leather upper and lining/rubber sole Made in Portugal more

'Penny' Loafers

Men's Thom Browne 'Penny' Loafers - Black 'Penny' pebble grain leather loafers with lightweight rubber sole and tricolor web detail at the back. Gender: Men. Material: 80% CALF LEATHER 20% RUBBER. Color: Black. Made in: IT. Product ID: MFD054G00198001.... more

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

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

Tevin Penny Loafer

Men's Thomas & Vine Tevin Penny Loafer - Black - Loafers Thomas & Vine Tevin Men s Loafer Live your best life in the Tevin men s Loafer from Thomas & Vine. With a recycled textile upper featuring leather accents, this penny Loafer supports your best... more

Penny Loafer

Men's Canali Penny Loafer - Brown - Loafers Tastefully tumbled calfskin lends refined texture to the entirety of a polished penny loafer carved with a curved slot. Leather upper, lining and sole Made in Italy more

Aalto Penny Loafer

Men's ALDO Aalto Penny Loafer - Black - Loafers A herringbone-textured vamp lends a contemporary touch to this leather penny loafer set on a flexible sole. Leather upper/recycled-polyester, textile and synthetic lining/rubber sole Imported more

Penny Loafer Slingback Sandal

Men's Thom Browne Penny Loafer Slingback Sandal - 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 strap with buckle... more

Alvin Penny Loafer

Men's Stuart Weitzman Alvin Penny Loafer - Black - Loafers A classic penny keeper and apron toe add timeless sophistication to a leather loafer grounded by a treaded rubber sole. Leather upper and lining/rubber sole Made in Italy more