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Best Seller
Bolama Penny Loafer

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

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...

Lyst Marketplace

$490.00 $269.50

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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

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.

Lyst Marketplace

$370.00 $185.00

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Best Seller
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

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...

Lyst Marketplace

$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

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...

Lyst Marketplace

$400.00

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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

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.

Lyst Marketplace

$587.78 $445.78

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Wakith Suede Apron Toe Penny Loafer

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

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.

Lyst Marketplace

$128.00

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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

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.

Lyst Marketplace

$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

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...

Lyst Marketplace

$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

James Penny Loafers

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

Lyst Marketplace

$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

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...

Lyst Marketplace

$270.00 $135.00

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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

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.

Lyst Marketplace

$560.00

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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

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...

Lyst Marketplace

$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

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...

Lyst Marketplace

$450.00

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Townee Penny Loafer

Townee Penny Loafer

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

Townee Penny Loafer

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...

Lyst Marketplace

$380.00

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Solomeo Penny Loafer

Solomeo Penny Loafer

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

Solomeo Penny Loafer

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.

Lyst Marketplace

$450.00

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Randolph Leather Penny Loafers

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

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

Lyst Marketplace

$425.00

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Randolph Leather Penny Loafers

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

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.

Lyst Marketplace

$450.00

FREE shipping

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Seaport Penny Loafer

Seaport Penny Loafer

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

Seaport Penny Loafer

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...

Lyst Marketplace

$105.00

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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

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...

Lyst Marketplace

$990.00

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Carlos Penny Loafer

Carlos Penny Loafer

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

Carlos Penny Loafer

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.

Lyst Marketplace

$990.00

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Walden Penny Loafer

Walden Penny Loafer

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

Walden Penny Loafer

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.

Lyst Marketplace

$199.00

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Walden Penny Loafer

Walden Penny Loafer

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

Walden Penny Loafer

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.

Lyst Marketplace

$210.00 $168.00

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Newman Leather Penny Loafers

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 0.50 in / 15 mm stacked heel Round moc toe Penny keeper strap Padded... ... 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 0.50 in / 15 mm stacked heel Round moc toe Penny keeper strap Padded...

Lyst Marketplace

$375.00

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Tucker Penny Loafer

Tucker Penny Loafer

Men's ALDO Tucker Penny Loafer - Black - Loafers A classic penny keeper and rich leather lend luxe elements to a sophisticated loafer set on a cushioned footbed and flexible rubber sole. ... more

Tucker Penny Loafer

Men's ALDO Tucker Penny Loafer - Black - Loafers A classic penny keeper and rich leather lend luxe elements to a sophisticated loafer set on a cushioned footbed and flexible rubber sole.

Lyst Marketplace

$135.00

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Hamilton Penny Strap Driving Loafer

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

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,...

Lyst Marketplace

$175.00 $122.50

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Randolph Leather Penny Loafers

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

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

Lyst Marketplace

$425.00

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Moana Penny Loafer

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

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.

Lyst Marketplace

$178.00

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Penny Loafer

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

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...

Lyst Marketplace

$880.00

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Natal Penny Loafer

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

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...

Lyst Marketplace

$160.00

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Penny Loafer

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

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...

Lyst Marketplace

$639.00

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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

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...

Lyst Marketplace

$390.00

FREE shipping

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Taylor Penny Loafer

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

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.

Lyst Marketplace

$120.00

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Penny-slot Leather Loafers

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

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.

Lyst Marketplace

$929.76 $562.32

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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

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

Lyst Marketplace

$250.00

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Penny Loafer With Gancini Ornament

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

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...

Lyst Marketplace

$950.00 $571.00

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Seaport Penny Loafer

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

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...

Lyst Marketplace

$105.00

FREE shipping

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Natal Penny Loafer

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

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...

Lyst Marketplace

$160.00

FREE shipping

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Wynston Penny Loafer

Wynston Penny Loafer

Men's Vince Camuto Wynston Penny Loafer - Brown - Loafers Bring laidback, vintage flair to a casual or professional look with the Wynston penny loafer from Vince Camuto. The classic look ensures styling ease for this leather pair. Suede or leather... ... more

Wynston Penny Loafer

Men's Vince Camuto Wynston Penny Loafer - Brown - Loafers Bring laidback, vintage flair to a casual or professional look with the Wynston penny loafer from Vince Camuto. The classic look ensures styling ease for this leather pair. Suede or leather...

Lyst Marketplace

$109.99

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Brown Calf Suede Varsity Penny Loafers

Brown Calf Suede Varsity Penny Loafers

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

Brown Calf Suede Varsity Penny Loafers

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

Lyst Marketplace

$820.00

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