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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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    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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    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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    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. more

    $158.00

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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. more

    $160.00

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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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    American Eagle Outfitters Shoes | American Eagle Retro Oxblood Red/Black Slip On Chunky Heel Penny Loafers Sz 8.5 | Color: Black/Red | Size: 8.5

    American Eagle Outfitters Shoes | American Eagle Retro Oxblood Red/Black Slip On Chunky Heel Penny Loafers Sz 8.5 | Color: Black/Red | Size: 8.5

    Great Preowned Condition Normal Wear With Very Small Scratch On Toe Of Left Shoe. See Last Pic For Details!!! 2.5” Chunky Heel Great Color Combo Retro Women’s Size 8.5 more

    $26.00

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    J. Crew Shoes | J Crew Shoes Mens 9 Penny Loafer Leather Slip On Classic Lifestyle Moc Toe Brown | Color: Brown | Size: 9

    J. Crew Shoes | J Crew Shoes Mens 9 Penny Loafer Leather Slip On Classic Lifestyle Moc Toe Brown | Color: Brown | Size: 9

    Used J Crew Shoes Mens 9 Penny Loafer Leather Slip On Classic Lifestyle Moc Toe Brown Scuffs And Creasing On Uppers, See Photos. Gently Used And In Good Condition. Pair In Photos Is The Exact Pair You Are Purchasing. Feel Free To Ask Any Questions! New... more

    $45.00

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    Coach Shoes | Coach Mott Driver Leather Penny Loafers Classic Logo Brown Fg1105 Men's Size 8 | Color: Black/Brown | Size: 8

    Coach Shoes | Coach Mott Driver Leather Penny Loafers Classic Logo Brown Fg1105 Men's Size 8 | Color: Black/Brown | Size: 8

    Coach Mott Driver Leather Penny Loafers Classic Logo Brown Fg1105 Men's Size 8 No Box. Shoes Are Used And May Show Signs Of Wear. Please Double Check Photos For Condition. Pair In Photos Is The Exact Pair You Are Purchasing. Please Reach Out With Any... more

    $60.00

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    Rockport Classic Loafer Lite Penny - Mens 10 Brown Slip On W

    Rockport Classic Loafer Lite Penny - Mens 10 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 14 Brown Slip On W

    Rockport Classic Loafer Lite Penny - Mens 14 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 8 Brown Slip On W

    Rockport Classic Loafer Lite Penny - Mens 8 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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    Classic Dan Penny Loafer - Black - Sebago Flats

    Classic Dan Penny Loafer - Black - Sebago Flats

    Women's Sebago Classic Dan Penny Loafer - Black - Loafers Hand-sewn and classically styled, this beefroll penny loafer is crafted of polished leather with a breathable, unlined upper and waterproof, flexible sole. more

    $250.00

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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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    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

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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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    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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    Sw Club Classic Penny Loafer Men's

    Sw Club Classic Penny Loafer Men's

    Men's Stuart Weitzman Sw Club Classic Penny Loafer Men's - Black - Loafers The SW CLUB CLASSIC PENNY LOAFER is timeless - not traditional. Modern polished lines define the look from its subtly protruding welt to its broader rounded square toe. Note its... more

    $495.00

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    Thom E Classic Penny Loafers

    Thom E Classic Penny Loafers

    Men's Thom Browne Thom E Classic Penny Loafers - Black Calfskin suede loafers in navy. more

    $750.00

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    Classic Dan Leather Tassel Penny Loafers

    Classic Dan Leather Tassel Penny Loafers

    Women's Sebago Classic Dan Leather Tassel Penny Loafers - White Sebago "Dan" made of smooth corrected grain leather to stand the test of time and handsewn with the finest craftsmanship, these 4 seasons slip on beefroll penny loafer mocs come with upper... more

    $280.00

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    Classic Penny Loafer

    Classic Penny Loafer

    Men's Rockport Classic Penny Loafer - Brown - 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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    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

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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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    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

    $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. 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

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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. more

    $175.00

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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

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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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    Sensory Penny Loafer

    Sensory Penny Loafer

    Men's Dune Sensory Penny Loafer - Black - Loafers Plush velvet enriches a charming loafer in a clean, classic silhouette. more

    $160.00

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    Knox Flexible Penny Loafer

    Knox Flexible Penny Loafer

    Men's Nordstrom Knox Flexible Penny Loafer - Brown - Loafers Complete your office ensembles with this classic penny loafer fashioned from soft suede. more

    $99.95

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    Silas Penny Loafer

    Silas Penny Loafer

    Men's Dune Silas Penny Loafer - Blue - Loafers A penny keeper strap and apron toe lend classic sophistication to this crisp loafer crafted from velvety suede. more

    $160.00

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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

    $178.00

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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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    Wynston Penny Loafer

    Wynston Penny Loafer

    Men's Vince Camuto Wynston Penny Loafer - Brown - Loafers A contoured penny strap and rounded moc toe bring classic detailing to a loafer that offers a sophisticated appearance. more

    $149.00 $111.75

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    Berkly Penny Loafer

    Berkly Penny Loafer

    Men's Dune Berkly Penny Loafer - Brown - Loafers Pull together your look with the effortlessly polished style of this contemporary take on a classic penny loafer. more

    $140.00

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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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    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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    Moana Penny Loafer

    Moana Penny Loafer

    Men's Rodd & Gunn Moana Penny Loafer - Blue - Loafers Smooth suede invigorates the look of a classic penny loafer grounded by a lightweight rubber sole. more

    $178.00

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