Best Seller
Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 10 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 10 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 14 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 14 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Best Seller
Brooks Brothers Men's Westport Penny Loafers | Black | Size 11 D

Brooks Brothers Men's Westport Penny Loafers | Black | Size 11 D

Full-grain leather and our hand-sewn English moccasin uppers, with beef roll detail, set the standard for classic All-American style. Our hand-stained heritage leather outsoles house a memory foam footbed that offers all-day comfort.100%... more

$248.00

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Men's Essex Drew Shoe by Drew in Black Leather (Size 9 M)

Men's Essex Drew Shoe by Drew in Black Leather (Size 9 M)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Wide Width Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 1/2 W)

Wide Width Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 1/2 W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 10 N)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 10 N)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Brooks Brothers Men's Westport Penny Loafers | Black | Size 12 D

Brooks Brothers Men's Westport Penny Loafers | Black | Size 12 D

Full-grain leather and our hand-sewn English moccasin uppers, with beef roll detail, set the standard for classic All-American style. Our hand-stained heritage leather outsoles house a memory foam footbed that offers all-day comfort.100%... more

$248.00

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Brooks Brothers Men's Westport Penny Loafers | Black | Size 13 D

Brooks Brothers Men's Westport Penny Loafers | Black | Size 13 D

Full-grain leather and our hand-sewn English moccasin uppers, with beef roll detail, set the standard for classic All-American style. Our hand-stained heritage leather outsoles house a memory foam footbed that offers all-day comfort.100%... more

$248.00

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Classic Leather Penny Loafers

Classic Leather Penny Loafers

Men's Ted Baker Classic Leather Penny Loafers - Black Classic, comfortable and easy to wear, this versatile penny loafer made with soft leather features traditional moc-toe detailing and a lower heel to relax the overall feel. Leather or leather and... more

$170.00

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American Classics Pinch Penny Loafer

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

$228.00

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American Classics Penny Loafer

American Classics Penny Loafer

Men's Cole Haan American Classics Penny Loafer - Brown - Loafers Spruce up your smart casual look donning the American Classics penny loafer from Cole Haan. This timeless loafer flaunts a lightweight leather construction with EVA foam footbed and... more

$159.99 $129.98

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 14 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 14 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 7 1/2 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 7 1/2 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 1/2 4W)

Men's Essex Drew Shoe by Drew in Burgundy Leather (Size 8 1/2 4W)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Men's Essex Drew Shoe by Drew in Black Leather (Size 11 1/2 M)

Men's Essex Drew Shoe by Drew in Black Leather (Size 11 1/2 M)

This Drew mens classic slip-on penny loafer offers a timeless style tailored to dress up any outfit. The Essex by Drew® features added depth with a removable footbed with ultimate arch build-up. Premium quality leather and lightweight, shock absorbing... more

$199.99

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Modern Classics Penny Loafer

Modern Classics Penny Loafer

Men's Cole Haan Modern Classics Penny Loafer - Brown - Loafers A traction-enhancing sole adds everyday utility to a classic penny loafer shaped from smooth, burnished leather. Traction-enhancing outsole with rubber pods Leather upper and lining/leather... more

$298.00

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Classic Joe Penny Loafers

Classic Joe Penny Loafers

Men's Sebago Classic Joe Penny Loafers - Black 100% Leather. Made in Mexico. more

$263.30 $203.66

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Classic Joe Penny Loafers

Classic Joe Penny Loafers

Men's Sebago Classic Joe Penny Loafers - Black 100% Leather. Made in Mexico. more

$246.49 $180.18

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American Classics Pinch Penny Loafer

American Classics Pinch Penny Loafer

Men's Cole Haan American Classics Pinch Penny Loafer - Black - 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

$228.00

FREE shipping

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American Classics Pinch Penny Loafer

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

$228.00

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Club Classic Penny Loafer

Club Classic Penny Loafer

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

$495.00

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Club Classic Penny Loafer

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

$495.00

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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. Leather upper, lining and sole Imported more

$175.00

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Larson Leather Penny Loafer

Larson Leather Penny Loafer

Men's G.H.BASS Larson Leather Penny Loafer - Gray - 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

$175.00

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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. Leather upper, lining and sole Imported more

$175.00

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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. Leather upper, lining and sole Imported more

$175.00

FREE shipping

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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. Leather upper, lining and sole Imported more

$175.00

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Diezma Ii Leather Penny Loafers

Diezma Ii Leather Penny Loafers

Men's Magnanni Shoes Diezma Ii Leather Penny Loafers - Brown Magnanni classic loafers in breathable supple calfskin leather Línea Flex blends classic bologna construction with additional features for increased flexibility Stacked heel Almond moc toe... more

$450.00

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Diezma Ii Leather Penny Loafers

Diezma Ii Leather Penny Loafers

Men's Magnanni Shoes Diezma Ii Leather Penny Loafers - Black Magnanni classic loafers in breathable supple calfskin leather Línea Flex blends classic bologna construction with additional features for increased flexibility Stacked heel Almond moc toe... more

$450.00

FREE shipping

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Logan Leather Penny Loafer

Logan Leather Penny Loafer

Men's G.H.BASS Logan Leather Penny Loafer - Brown - Loafers This classic penny loafer showcases handsome moc stitching and flat-strap styling for all-day, every-day sophistication. Leather upper, lining and sole Imported more

$175.00

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Rich Leather Penny Loafers with Rubber Sole

Rich Leather Penny Loafers with Rubber Sole

Men's Bruno Magli Rich Leather Penny Loafers with Rubber Sole - Black A classic penny keeper and streamlined profile distinguish a rich leather loafer grounded by a durable rubber sole. Leather upper and lining/rubber sole Made in Italy more

$375.00

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Saffiano Leather Penny Loafers

Saffiano Leather Penny Loafers

Men's Prada Saffiano Leather Penny Loafers - Black Crafted of saffiano leather, these classic Prada penny loafers rest on a comfortable rubber sole. Leather upper Slip-on style Leather lining Rubber sole Padded insole Made in Italy ABOUT THE BRAND... more

$875.00

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Cooper Leather Penny Loafers

Cooper Leather Penny Loafers

Men's COACH Cooper Leather Penny Loafers - Black Coach takes a more subdued approach with the Cooper penny loafer, featuring a partially pebble-grained body. The classic silhouette is embraced by butter leather, resting on a lug sole for reliable... more

$401.20 $201.28

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Leather Penny Moc Loafers

Leather Penny Moc Loafers

Men's Ted Baker Leather Penny Moc Loafers - Black Classic, comfortable and easy to wear, this versatile penny loafer made with soft leather features traditional moc-toe detailing and a lower heel to relax the overall feel. Leather or leather and... more

$170.00

FREE shipping

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Rich Leather Penny Keeper Loafers

Rich Leather Penny Keeper Loafers

Men's Bruno Magli Rich Leather Penny Keeper Loafers - Black A classic penny keeper and streamlined profile distinguish a rich leather loafer grounded by a durable rubber sole. Leather upper and lining/rubber sole Made in Italy more

$375.00

FREE shipping

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Dickerson Penny Loafer

Dickerson Penny Loafer

Men's To Boot New York Dickerson Penny Loafer - Black - Loafers A classic penny keeper and sleek leather construction lend timeless sophistication to a polished loafer perfect for any occasion. Leather upper and lining/leather and rubber sole Made in... more

$425.00 $233.75

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Sawyer Penny Loafer

Sawyer Penny Loafer

Men's Blake McKay Sawyer Penny Loafer - Brown - Loafers A classic penny keeper and an apron toe lend timeless sophistication to a leather loafer coated in a water-resistant finish. Water resistant OrthoLite® footbed Leather upper/leather and textile... more

$150.00

FREE shipping

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Titouan Penny Loafer

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

$289.00

FREE shipping

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Lastra Penny Loafer

Lastra Penny Loafer

Men's Bruno Magli Lastra Penny Loafer - Black - Loafers Rich leather refines this sleek Italian-made loafer detailed with subtle double-stitched accents and a classic penny strap. Leather upper and lining/rubber sole Made in Italy more

$298.00

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More information about Men's Shoes

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