Best Seller
Thorne Penny Loafer

Thorne Penny Loafer

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

$990.00

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Thorne Penny Loafer

Thorne Penny Loafer

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

$990.00

FREE shipping

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Best Seller
Richee Penny Loafer

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

$370.00 $203.50

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Vinnee Penny Loafer

Vinnee Penny Loafer

Men's VINNY'S Vinnee Penny Loafer - White - Loafers A classic penny keeper and an apron toe lend timeless sophistication to a leather loafer that will elevate your polished style. Leather upper and lining/rubber sole Made in Portugal Black Owned/Founded. more

$400.00

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Arezzo Burnished Leather Penny Loafers

Arezzo Burnished Leather Penny Loafers

Men's Bruno Magli Arezzo Burnished Leather Penny Loafers - Brown Bruno Magli "Arezzo" loafer in smooth, handburnished calf leather. Rounded apron toe; braided leather moccasin seam. 1" stacked heel. Notched vamp. Penny keeper strap. Slipon style.... more

$395.00

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Lucien Suede Penny Loafers

Lucien Suede Penny Loafers

Men's Magnanni Shoes Lucien Suede Penny Loafers - Brown Magnanni "Lucien" penny loafers in calf suede Stacked heel Almond-shaped apron toe Penny keeper strap Leather lining and outsole Slip-on style Made in Spain. more

$495.00

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Calfskin Driver Penny Loafers

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

$250.00

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Nathan Croc Embossed Penny Loafer

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

$325.00

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Richee Two-tone lugged Penny Loafer

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

$400.00

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Penny Loafer

Penny Loafer

Men's Thom Browne Penny Loafer - Blue - Loafers Supple suede in a soft blue hue elevates a handsome Italian loafer featuring a sleek apron toe and a bit of brand coloring on the heel loop. Leather upper, lining and sole Made in Italy Designer Shoes. more

$820.00

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Penny Bar Loafers

Penny Bar Loafers

Men's Tod's Penny Bar Loafers - Brown Dimensions: Heel: 2.5cm, Sole: 1.5cm 100% Suede, 100% Rubber, 100% Leather. Made in Italy. more

$523.66 $452.44

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Daniel Leather Penny Loafers

Daniel Leather Penny Loafers

Men's Magnanni Shoes Daniel Leather Penny Loafers - Brown Magnanni "Daniel" penny loafers in premium calf leather Features bologna construction for added breathability and flexibility Stacked heel Round toe Penny strap at vamp Leather lining and trim... more

$425.00

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Jimmy 2 Suede Penny Loafers

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

$285.00

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Silas Suede Penny Loafers

Silas Suede Penny Loafers

Men's Bruno Magli Silas Suede Penny Loafers - Brown Bruno Magli "Silas" loafers in soft Italian suede 0.50 in / 15 mm stacked heel Round moc toe; contrast stitching Penny keeper strap Leather lining Rubber outsole Item Weight (Lbs.): 3.0 Slipon style... more

$298.00

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Townee Penny Loafer

Townee Penny Loafer

Men's VINNY'S Townee Penny Loafer - Green - Loafers Croc-embossed leather from Italy gives a luxurious look and feel to a handsome loafer set atop a soft and cushioned footbed. Cushioned footbed Leather upper, lining and sole Made in Portugal Black... more

$340.00

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Jayce Suede Penny Loafers

Jayce Suede Penny Loafers

Men's Donald J Pliner Jayce Suede Penny Loafers - Blue Donald J Pliner "Jayce" penny loafers in soft suede Stacked heel Square toe Penny keeper strap Padded memory foam footbed Leather lining Leather sole Slipon style Made in Italy more

$295.00

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Harlan Penny Loafer

Harlan Penny Loafer

Men's Paul Stuart Harlan Penny Loafer - Brown - Loafers Elevate your look with the suave, classic style of this Italian-crafted penny loafer. Leather upper, lining and sole Made in Italy Men's Shoes. more

$595.00

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L'asola Penny Loafer

L'asola Penny Loafer

Men's Zegna L'asola Penny Loafer - Brown - Loafers Named for the buttonholes in finely tailored menswear, this suede loafer from the Italian label features a clean, classic silhouette topped with contrast band. Leather upper, lining and sole Made in... more

$990.00

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Harper Penny Loafer

Harper Penny Loafer

Men's Mephisto Harper Penny Loafer - Black - 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

$349.00

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Mocassino Penny Loafer

Mocassino Penny Loafer

Men's Tod's Mocassino Penny Loafer - White - Loafers A classic penny keeper strap adds a refined flourish to a sharp Italian loafer softened by a supple suede upper. Leather upper, lining and sole Made in Italy Designer Shoes. more

$825.00

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Jago Suede Penny Loafer

Jago Suede Penny Loafer

Men's AllSaints Jago Suede Penny Loafer - Natural - Loafers Soft suede and contrast stitching further the relaxed, wear-everywhere appeal of a penny loafer set on a sole of cushy crepe rubber. Leather upper and lining/rubber sole Made in Portugal. more

$299.00

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L'asola Suede Penny Loafer

L'asola Suede Penny Loafer

Men's Zegna L'asola Suede Penny Loafer - Blue - 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... more

$990.00

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Townee Tri-tone Penny Loafer

Townee Tri-tone Penny Loafer

Men's VINNY'S Townee Tri-tone 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. Leather upper, lining and sole Made in Portugal Black... more

$350.00

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Tonio Penny Loafer

Tonio Penny Loafer

Men's Bruno Magli Tonio Penny Loafer - Brown - Loafers Classic style meets everyday comfort in this moc-toe penny loafer fashioned from rich Italian leather. Cushioned footbed Leather upper and lining/leather and rubber sole Made in Italy. more

$395.00

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Jimmy Penny Loafer

Jimmy Penny Loafer

Men's Donald J Pliner Jimmy Penny Loafer - Orange - Loafers Reptile-embossed leather pairs with velvety-soft suede on this richly textured penny loafer grounded on a lightweight, sneaker-inspired sole. Memory foam cushioning Leather upper and... more

$285.00 $199.50

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Lalo Leather Penny Loafers

Lalo Leather Penny Loafers

Men's Magnanni Shoes Lalo Leather Penny Loafers - Brown Magnanni "Lalo" loafers in soft leather Flat heel Almond toe Penny keeper strap Comfortable outsole Leather lining and trim Slipon style Made in Spain more

$450.00

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Durbin Penny Loafer

Durbin Penny Loafer

Men's Gordon Rush Durbin Penny Loafer - Gray - Loafers Fine craftsmanship and Italian leather brings a refined look to a timeless loafer with a breathable leather lining and Ortho Lite® insole that offer lasting comfort. more

$245.00 $169.90

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Rucci Penny Loafer

Rucci Penny Loafer

Men's Florsheim Rucci Penny Loafer - Black - Loafers Mixed textures and a classic penny keeper lend visual intrigue to a sophisticated leather loafer set on a cushioned footbed and flexible rubber sole. more

$130.00

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Gommino Penny Slot Loafers

Gommino Penny Slot Loafers

Men's Tod's Gommino Penny Slot Loafers - Gray Dimensions: Heel: 3.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. more

$630.53 $472.14

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Fred Penny Loafer

Fred Penny Loafer

Men's Sandro Moscoloni Fred Penny Loafer - Blue - Loafers The Fred penny loafer from Sandro Moscoloni is a classic add to your wardrobe. Finsih off a formal look with this sleek leather pair that sports a cushioned footbed for added comfort. Leather... more

$179.99

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Wilde Vegas Strip Leather Penny Loafers

Wilde Vegas Strip Leather Penny Loafers

Men's Duke & Dexter Wilde Vegas Strip Leather Penny Loafers - Black DUKE + DEXTER exclusive "Wilde" penny loafers in bicolor leather with contrast topstitching Features the Las Vegas Strip race car motif 1.00 in / 25 mm stacked heel Round moc toe Penny... more

$340.00

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Gommino Round Toe Penny Loafers

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

$587.78 $445.78

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Larson Leather Penny Loafer

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. more

$175.00

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Athens Penny Driving Loafer

Athens Penny Driving Loafer

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

$129.00

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James Penny Loafers

James Penny Loafers

Men's Tricker's James Penny Loafers - Black 100% Leather. Made in United Kingdom. more

$657.51 $570.99

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Yardee Penny Loafer

Yardee Penny Loafer

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

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Garret Penny Loafer

Garret Penny Loafer

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

$560.00

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Croftwood Check Leather Penny Loafer

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

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Bateau Water Resistant Penny Loafer

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

$845.00

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Sw Club La Penny Loafer Men's

Sw Club La Penny Loafer Men's

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

$450.00

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