Best Seller
Brooks Brothers Men's Westport Penny Loafers | Black | Size 10 D

Brooks Brothers Men's Westport Penny Loafers | Black | Size 10 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 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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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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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. more

$228.00

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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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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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J. Crew Shoes | J. Crew Mens Classic Black Leather Penny Loafer Slip On Size 10.5 | Color: Black | Size: 10.5

J. Crew Shoes | J. Crew Mens Classic Black Leather Penny Loafer Slip On Size 10.5 | Color: Black | Size: 10.5

Ideal Black Leather Penny Loafers To Add To Any Man's Wardrobe. Pre-Owned And In Very Gently Used Condition. Minor Creasing. See Pictures. more

$55.00

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Ralph Lauren Shoes | *Ralph Lauren Camel Brown Leather Classic Penny Loafer Polo Sport - Size 10d | Color: Brown | Size: 10d

Ralph Lauren Shoes | *Ralph Lauren Camel Brown Leather Classic Penny Loafer Polo Sport - Size 10d | Color: Brown | Size: 10d

Ralph Lauren Camel Brown Leather Classic Penny Loafer Polo Sport . Classic Caramel Colored Penny Loafer Wide Width. All Measurements Are Approximate. Very Good Condition. Please See Photos For More Details. Size 10d. more

$169.00

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J. Crew Shoes | J. Crew Men's Kenton Suede Penny Loafers Shoes Classic Navy Blue Size 12 - A6312 | Color: Blue | Size: 12

J. Crew Shoes | J. Crew Men's Kenton Suede Penny Loafers Shoes Classic Navy Blue Size 12 - A6312 | Color: Blue | Size: 12

Pre/Owned Excellent Condition, No Damage, Sole Minor Sign Of Wear. J. Crew Men's Kenton Suede Penny Loafers Shoes Classic Navy Blue Size 12, Upper & Lining Material: Leather. Great Condition. Model A6312. Offers Are Welcome. more

$126.00

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Rockport Classic Loafer Lite Penny - Mens 11.5 Brown Slip On W

Rockport Classic Loafer Lite Penny - Mens 11.5 Brown Slip On W

*Rockport's handsome penny loafer delivers all-day comfort and timelessly traditional style *Leather upper with moc toe and penny keeper strap *Sponge EVA footbed forms to the shape of the foot for a personalized fit *Dewix anti-microbial linings wick... more

$114.95

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Rockport Classic Loafer Lite Penny - Mens 11 Brown Slip On W

Rockport Classic Loafer Lite Penny - Mens 11 Brown Slip On W

*Rockport's handsome penny loafer delivers all-day comfort and timelessly traditional style *Leather upper with moc toe and penny keeper strap *Sponge EVA footbed forms to the shape of the foot for a personalized fit *Dewix anti-microbial linings wick... more

$114.95

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Rockport Classic Loafer Lite Penny - Mens 10.5 Brown Slip On W

Rockport Classic Loafer Lite Penny - Mens 10.5 Brown Slip On W

*Rockport's handsome penny loafer delivers all-day comfort and timelessly traditional style *Leather upper with moc toe and penny keeper strap *Sponge EVA footbed forms to the shape of the foot for a personalized fit *Dewix anti-microbial linings wick... more

$114.95

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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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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. more

$298.00

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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

$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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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 $131.25

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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 $131.25

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Wakith Apron Toe Penny Loafer

Wakith Apron Toe Penny Loafer

Men's ALDO Wakith Apron Toe Penny Loafer - Brown - Loafers Classic and versatile, this loafer made of polished leather features a contoured penny strap and classic apron toe for a smart, streamlined look. more

$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

$175.00 $131.25

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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

$199.00

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Walden Penny Loafer

Walden Penny Loafer

Men's Camper Walden Penny Loafer - Pink - Loafers A simple, classic design underscores the timeless appeal of a burnished leather penny loafer complete with comfort-enhancing OrthoLite® cushioning. more

$199.00

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Ascanio Penny Loafer

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

$130.00

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Townee Penny Loafer

Townee Penny Loafer

Men's VINNY'S Townee Penny Loafer - Black - Loafers Smooth calfskin leather shapes this classic penny loafer featuring a soft, comfort-focused footbed. more

$350.00

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Ascanio Penny Loafer

Ascanio Penny Loafer

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

$130.00

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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

$135.00

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Lyles Penny Loafer

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

$165.00

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Phillip Penny Loafer

Phillip Penny Loafer

Men's Sandro Moscoloni Phillip Penny Loafer - Brown - Loafers Finish off a semi-formal, casual or professional look with the versatile Phillip penny loafer from Sandro Moscoloni. This leather pair sports a classic look offset by a lugged sole for... more

$179.99

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Newman Penny Loafer

Newman Penny Loafer

Men's Allen Edmonds Newman Penny Loafer - Black - Loafers A classic penny keeper and antique finish lend timeless sophistication to a leather loafer that will elevate your desk-to-dinner style. more

$395.00

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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

$370.00

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Rucci Weave Penny Loafer

Rucci Weave Penny Loafer

Men's Florsheim Rucci Weave Penny Loafer - Black - Loafers Amp up your formal ensemble with the Rucci Weave penny loafer from Florsheim. Intricate woven patterns bring unique charm to the classic design of this leather slip-on. Soft lining, fully... more

$129.99

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Athens Penny Driving Loafer

Athens Penny Driving Loafer

Men's Johnston & Murphy Athens Penny Driving Loafer - Brown - 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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Lyles Penny Loafer

Lyles Penny Loafer

Men's Johnston & Murphy Lyles Penny Loafer - Gray - 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

$165.00

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Thom E Penny Loafer Slingback Sandal At Nordstrom

Thom E Penny Loafer Slingback Sandal At Nordstrom

Men's Thom Browne Thom E Penny Loafer Slingback Sandal At Nordstrom - Loafers Thom Browne continues to redefine wardrobe classics with this smooth leather slingback sandal boasting the cutout shell of a traditional penny loafer. Adjustable slingback... more

$820.00

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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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Decio Water Resistant Penny Loafer

Decio Water Resistant Penny Loafer

Men's Geox Decio Water Resistant Penny Loafer - Black - Loafers A classic penny keeper and rich leather upper distinguish a sophisticated loafer outfitted with comfortable cushioning and a signature tech sole. more

$230.00

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Belted Penny Loafer

Belted Penny Loafer

Men's J.W. Anderson Belted Penny Loafer - Brown - Loafers The classic penny loafer gets updated with a logo-engraved buckled belt wrapping the moc-stitched toe. Padded footbed Leather upper and lining/rubber sole Made in Italy Designer Shoes. more

$875.00

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Zaffiro Penny Loafer

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

$129.99

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Rucci Apron Toe Penny Loafer

Rucci Apron Toe Penny Loafer

Men's Florsheim Rucci Apron Toe Penny Loafer - Brown - Loafers A classic penny strap and simple apron toe bring understated distinction to a loafer made of fine-grain leather that adds polish to any formal look. more

$130.00

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