Best Seller
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 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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Best Seller
American Classics Penny Loafer

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

$158.00

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American Classics Penny Loafer

American Classics Penny Loafer

Men's Cole Haan American Classics Penny Loafer - Natural - 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... more

$160.00

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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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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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Coach Shoes | Coach Penny Loafers In Black Pebbled Leather | Color: Black | Size: 5.5

Coach Shoes | Coach Penny Loafers In Black Pebbled Leather | Color: Black | Size: 5.5

Coach American Luxury Leather Goods Brand Classic Penny Loafers With Black Metal Coin Upper In Black Pebbled Leather Lined In Tan Leather Rubber Treaded Sole In Black Excellent Pre-Owned Condition, Barely Worn, No Flaws, Sanitized more

$60.00

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American Classics Pinch Penny Loafer - Brown - Cole Haan Slip-Ons

American Classics Pinch Penny Loafer - Brown - Cole Haan Slip-Ons

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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Ellowyn Penny Loafer - Black - Clarks Flats

Ellowyn Penny Loafer - Black - Clarks Flats

Women's Clarks Ellowyn Penny Loafer - Black - Loafers Add to your casual or professional fits with the Ellowyn loafer from Clarks. The classic penny loafer look makes for versatile styling, while the cushy footbed and wedge sole ensure support... more

$70.00

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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 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

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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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Khrone Suede Loafer

Khrone Suede Loafer

Men's Alden Khrone Suede Loafer - Brown - Loafers A classic look and uncompromising comfort mark this American-made penny loafer crafted from supple suede, inside and out, and set on a brand-treaded sole. Leather upper and lining/synthetic sole Made in... more

$636.00

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American Classics Pinch Penny Loafer

American Classics Pinch Penny Loafer

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

$158.00

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Brown Classic Penny Loafers

Brown Classic Penny Loafers

Men's Thom Browne Brown Classic Penny Loafers - Black Buffed calfskin loafers in brown. more

$890.00 $650.00

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Airglow Classic Leather Penny Loafers

Airglow Classic Leather Penny Loafers

Women's Santoni Airglow Classic Leather Penny Loafers - Brown Santoni "Airglow" classic, hand burnished leather penny loafers Flat heel Round moc toe Notched vamp with keeper strap Slipon style Leather outsole Lining: Leather Made in Italy more

$920.00

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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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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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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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Gomma Classic Leather Penny Loafers

Gomma Classic Leather Penny Loafers

Women's Tod's Gomma Classic Leather Penny Loafers - Brown Tod's classic penny loafers in smooth calf leather 0.75 in / 20 mm flat heel Round moc toe Notched vamp with keeper strap Slipon style Lining: Virgin wool Rubber outsole Made in Italy more

$895.00

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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 $180.19

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Classic Penny Loafer

Classic Penny Loafer

Men's Rockport Classic Penny Loafer - Black - Loafers Comfort and style collide in this classic penny loafer from Rockport! Featuring sport technology for superior comfort and a stylish yet traditional design, this slip-on shoe will keep you looking... more

$79.99

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Burgundy Classic Penny Loafers

Burgundy Classic Penny Loafers

Men's Thom Browne Burgundy Classic Penny Loafers - Black Buffed calfskin loafers in burgundy. more

$750.00 $585.00

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Suede Classic Penny Loafers

Suede Classic Penny Loafers

Women's Tod's Suede Classic Penny Loafers - Blue Tod's soft suede classic penny loafers Flat heel Round moc toe Notched vamp with keeper strap Slipon style Rubber outsole Lining: Leather Made in Italy more

$695.00

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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. Cushioned footbed Leather upper/synthetic... more

$128.00

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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 - Blue - Loafers Classic and versatile, this loafer made of brushed suede features a contoured penny strap and classic apron toe for a smart, streamlined look. Cushioned footbed Leather upper/synthetic... more

$128.00

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Alfa Penny Driving Loafer

Alfa Penny Driving Loafer

Women's Coach and Four Alfa Penny Driving Loafer - Black - Loafers Slip on the classic Alfa Penny Driving mocassin from Coach and Four for a classic highlight to your look. The leather construction brings a luxe touch, and the driving sole with... more

$69.99 $59.98

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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

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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

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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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Penny Loafer

Penny Loafer

Men's Tod's Penny Loafer - Black - Loafers A classic keeper strap adds a refined flourish to a sharp Italian loafer crafted in soft leather. Leather upper and lining/rubber sole Made in Italy Men's Shoes more

$695.00

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Motor Penny Driving Loafer

Motor Penny Driving Loafer

Men's Florsheim Motor Penny Driving Loafer - Brown - Loafers From professional meetings to a laid-back brunch settings, the Florsheim Motor Penny driving loafer is the right pick. Woven-textured upper with classic stitching details uplifts this leather... more

$79.99

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Bristol Penny Loafer

Bristol Penny Loafer

Men's Eastland Bristol Penny Loafer - Black - Loafers Eastland Bristol Men's Penny Loafer Classic style is timeless with the Eastland Bristol penny Loafer. Featuring a leather upper with penny Loafer detailing, these Slip-Onshave a classy look. The... more

$139.99

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Motor Penny Driving Loafer

Motor Penny Driving Loafer

Men's Florsheim Motor Penny Driving Loafer - Black - Loafers From professional meetings to a laid-back brunch settings, the Florsheim Motor Penny driving loafer is the right pick. Woven-textured upper with classic stitching details uplifts this leather... more

$79.99

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Moana Penny Loafer

Moana Penny Loafer

Men's Rodd & Gunn Moana Penny Loafer - Gray - Loafers Smooth suede invigorates the look of a classic penny loafer grounded by a lightweight rubber sole. Leather upper and lining/rubber sole Imported more

$178.00 $142.40

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Spencer Penny Loafer

Spencer Penny Loafer

Men's Stacy Adams Spencer Penny Loafer - Blue - Loafers A classic penny keeper and moc toe add timeless elements to a burnished leather loafer grounded by a durable rubber sole. Removable, cushioned insole with arch support Leather and synthetic... more

$120.00

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