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Ravello Penny Loafer - Brown - To Boot New York Slip-Ons

Men's To Boot New York Ravello Penny Loafer - Brown - 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

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

Nathan Croc Embossed Penny Loafer

Men's Bruno Magli Nathan Croc Embossed Penny Loafer - Black - Loafers Elevate your professional footwear collection with an Italian-crafted loafer textured with luxurious croc-embossed leather and fitted with an antislip outsole. Leather upper and... 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

Lyles Penny Loafer

Men's Johnston & Murphy Lyles Penny Loafer - Brown - Loafers Classic and comfortable, this loafer made of polished leather features a traditional penny strap and a roomy moc toe for easy, wear-with-anything appeal. more

Carlos Penny Loafer

Men's Santoni Carlos Penny Loafer - Blue - 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

Penny Loafer

Men's Canali Penny Loafer - Natural - Loafers Beige suede lends velvety texture to a polished penny loafer carved with a curved slot and set on a grippy rubber sole. Leather upper/textile lining/rubber sole Made in Italy. more

Ascanio Penny Loafer

Men's Geox Ascanio Penny Loafer - Black - Loafers A classic penny keeper lends luxe appeal to a rich leather loafer grounded by a cushioned footbed and patented tech sole. more

Yardee Penny Loafer

Men's VINNY'S Yardee Penny Loafer - Natural - Loafers Enjoy the feel of luxurious Italian suede in this finely stitched penny loafer set atop a soft cushioned footbed. Cushioned footbed Leather upper, lining and sole Made in Portugal Black Owned/Founded. more

Club Classic Penny Loafer

Men's Stuart Weitzman Club Classic Penny Loafer - Black - 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

The Country Lug Sole Penny Loafer

Men's Taft The Country Lug Sole Penny Loafer - Brown - Loafers Buttery-soft leather tops this modern penny loafer built with a rubber commando lug sole, custom sidewall welt and a resoleable Blake construction. Leather upper and lining/rubber sole Made... more

Zaffiro Penny Loafer

Men's Florsheim Zaffiro Penny Loafer - Brown - Loafers Diversify your formal and professional wardrobe with the Zaffiro moc toe penny loafer from Florsheim. Crafted from leather, this pair sports a classic silhouette for a versatile addition to your... more

Jimmy 2 Suede Penny Loafers

Men's Donald J Pliner Jimmy 2 Suede Penny Loafers - Blue Donald J Pliner "Jimmy 2" penny loafers in suede with lizardembossed leather trim Flat chunky heel Round moc toe Penny keeper strap Padded memory foam footbed Leather lining Lightweight EVA... more

L'asola Penny Loafer

Men's Zegna L'asola Penny Loafer - Gray - Loafers Named for the buttonholes in finely tailored menswear, this iconic leather loafer from the Italian label features a clean, classic silhouette. Leather upper, lining and sole Made in Italy Men's Designer... more

Harper Penny Loafer

Men's Mephisto Harper Penny Loafer - Brown - Loafers This sophisticated loafer features a signature SOFT-AIR midsole that ensures flexible, cushioned comfort and a durable rubber sole for comfortable flexibility. Cushioned footbed with arch support... more

Avenue Penny Loafer

Men's Mezlan Avenue Penny Loafer - Brown - Loafers Smooth leather brings office-ready polish to a Spanish-crafted penny loafer finished with a streamlined apron toe. Leather upper and lining/rubber sole Made in Spain. more

Dougan Penny Loafer

Men's Ferragamo Dougan Penny Loafer - Green - Loafers A gleaming Gancio buckle adds a heritage touch to a classic penny loafer crafted from richly grained calfskin leather and updated with a chunky lugged sole. Leather upper and lining/synthetic sole... more

Rb Leather Penny Loafers

Men's Rag & Bone Rb Leather Penny Loafers - Natural Rag & Bone penny loafers in calf suede/leather Chunky heel Round moc toe Penny keeper strap Debossed logo on the side Chunky lug sole Vibram® outsole for state-of-the-art traction Lining: Leather... more

Hamilton Penny Strap Driving Loafer

Men's Marc Joseph New York Hamilton Penny Strap Driving Loafer - White - 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

Simon Iii Penny Strap Loafer

Men's Børn Simon Iii Penny Strap Loafer - Gray - Loafers Hand-sewn Opanka construction ensures durability in a leather loafer topped with a penny strap and built on a cushy, flexible footbed and grippy rubber sole. more

Alex Penny Loafer

Men's Vagabond Alex Penny Loafer - Black - Loafers Polished leather distinguishes a sophisticated moc-toe loafer designed with a traditional penny keeper slot across the vamp. more

Newman Leather Penny Loafers

Men's Allen Edmonds Newman Leather Penny Loafers - Black Allen Edmonds "Newman" penny loafers in premium calfskin leather with an antique finish Comfortable, handsewn construction 1.00 in / 25 mm stacked heel Round moc toe Penny keeper strap... more

Zenith Penny Loafer

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

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

'weejuns Larson' Penny Loafers

Men's G.H.BASS 'weejuns Larson' Penny Loafers - Brown G.H. BASS Weejuns Larson penny loafers handcrafted in leather. Leather interior and leather sole. Shoehorn included. Colours: Purple Composition: Leather Made in: El Salvador MPN: BA11010H. 100%... more

Carter Penny Loafer

Men's Bruno Magli Carter Penny Loafer - Black - Loafers A penny keeper strap and moc-toe stitching lend heritage charm to this sleek leather loafer grounded on a slip-resistant rubber sole. Leather upper and lining/rubber sole Made in Italy. more

'cap Vert' Penny Loafer

Men's Mephisto 'cap Vert' Penny Loafer - Black - Loafers Handcrafted by trained artisans, with an aniline-dyed water-repellent leather upper for the ultimate in breathability and durability. The latex foam midsole absorbs shock from walking and... more

Maioco Penny Loafer

Men's Bruno Magli Maioco Penny Loafer - Brown - Loafers A lightly cushioned footbed brings impeccable comfort to a smooth leather loafer handmade in Italy. Cushioned footbed Leather upper, lining and sole Made in Italy. more

Titouan Penny Loafer

Men's Mephisto Titouan Penny Loafer - Blue - 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

Jumbo Mixed Media Penny Loafer

Men's Amiri Jumbo Mixed Media Penny Loafer - Black - Loafers A superchunky lug sole with ridged texture elevates this loafer detailed with a textured knit vamp and monogram-logo 'coin' in the keeper strap. Leather and synthetic upper/leather... more

Avery Penny Loafer

Men's Gordon Rush Avery Penny Loafer - Brown - Loafers Hand-burnished Italian leather enriches a classic loafer with a breathable calfskin lining and Ortho Lite® cushioning for comfort. more

Bolama Penny Loafer

Men's Armando Cabral Bolama Penny Loafer - Gray - Loafers A serrated tongue and embellished penny keeper update this sleek leather loafer presenting the next evolution of a classic closet staple. Leather and textile upper/leather lining/leather and... more

Bristol Penny Loafer

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

Sneaker Sole Penny Loafer

Men's Canali Sneaker Sole Penny Loafer - Blue - Loafers A grippy rubber cupsole grounds the sporty look of a penny loafer cut from Italian suede and styled to elevate any casual outfit. Leather upper and lining/rubber sole Made in Italy. more

Warning Driving Penny Loafer

Men's J.M. Weston Warning Driving Penny Loafer - White - Loafers The softest shade of blue elevates a hand-stitched penny loafer fashioned in France from supple suede. Memory foam cushioning Leather upper and lining/rubber sole Made in France Men's... more

L'asola Suede Penny Loafer

Men's Zegna L'asola Suede Penny Loafer - Red - Loafers Named for the buttonholes in finely tailored menswear, this iconic suede loafer from the Italian label features a clean, classic silhouette. Leather upper and lining/leather and synthetic sole Made... more

Penny Logo-embossed Loafers

Men's Tod's Penny Logo-embossed Loafers - Green Dimensions: Heel: 3.5cm, Sole: 2.5cm 100% Calf Suede, 100% Calf Leather, 100% Rubber. Made in Italy. 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