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Smart Style: Penny Loafers!
Since its origin in the 1930s, the penny loafer has been one of the most versatile shoes in fashion. It earned its name thanks to the split-lip strap, commonly used as a way to add a decorative or functional touch (like a penny) to a pair. Appropriate for both men and women, casual and formal, this style is truly timeless.

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  • Tod's Men's Penny Loafer (Dk Red)


    Tod’s Men’s Penny Loafer (Dk Red)

    $490$369.00

  • testoni BASIC Men's Welly Loafer (Tan)


    testoni BASIC Men’s Welly Loafer (Tan)

    $525$199.00

  • Tod's Men's Loafer (Brown)


    Tod’s Men’s Loafer (Brown)

    $442$329.00

  • Joseph Abboud Men's Damon Loafer (Black)


    Joseph Abboud Men’s Damon Loafer (Black)

    $125$49.00

  • Joseph Abboud Men's Damon Loafer (Chestnut)


    Joseph Abboud Men’s Damon Loafer (Chestnut)

    $125$49.00

  • Bruno Magli Men's Partie Penny Moccasin (Black)


    Bruno Magli Men’s Partie Penny Moccasin (Black)

    $425$199.00

  • Bruno Magli Men's Partie Penny Moccasin (Bordeaux)


    Bruno Magli Men’s Partie Penny Moccasin (Bordeaux)

    $425$199.00

  • Bruno Magli Men's Partie Penny Moccasin (Brown)


    Bruno Magli Men’s Partie Penny Moccasin (Brown)

    $425$199.00

  • Salvatore Ferragamo Men's Triumph Loafer (Black)


    Salvatore Ferragamo Men’s Triumph Loafer (Black)

    $550$359.00

  • Salvatore Ferragamo Men's Triumph Loafer Slip-On (Brown)


    Salvatore Ferragamo Men’s Triumph Loafer Slip-On (Brown)

    $450$289.00

  • Salvatore Ferragamo Men's Alain 2 Loafer Slip-On (Navy)


    Salvatore Ferragamo Men’s Alain 2 Loafer Slip-On (Navy)

    $595$379.00

  • Mezlan Men's Slip on Driver with Strap and Buckle (Brown)


    Mezlan Men’s Slip on Driver with Strap and Buckle (Brown)

    $325$112.00

  • Mezlan Men's Slip on Driver with Strap and Buckle (Olive/Brown)


    Mezlan Men’s Slip on Driver with Strap and Buckle (Olive/Brown)

    $325$112.00

  • Mezlan Men's Slip on Driver with Strap and Buckle (Taupe/Brown)


    Mezlan Men’s Slip on Driver with Strap and Buckle (Taupe/Brown)

    $325$112.00

  • Mezlan Men's Penny Loafer Driving Moc (Brown/Tan)


    Mezlan Men’s Penny Loafer Driving Moc (Brown/Tan)

    $325$112.00

  • Mezlan Men's Penny Loafer Driving Moc (Taupe/Bone)


    Mezlan Men’s Penny Loafer Driving Moc (Taupe/Bone)

    $325$112.00

  • Robert Wayne Men's Reese Loafer (Black Leather)


    Robert Wayne Men’s Reese Loafer (Black Leather)

    $100$47.00

  • Robert Wayne Men's Reese Loafer (Grey Suede)


    Robert Wayne Men’s Reese Loafer (Grey Suede)

    $100$47.00

  • Stacy Adams Men's Quinton Loafer (Cement)


    Stacy Adams Men’s Quinton Loafer (Cement)

    $90$34.00

  • J. Artola Men's Stillwell Loafer (Dark Brown)


    J. Artola Men’s Stillwell Loafer (Dark Brown)

    $215$64.00

  • J. Artola Men's Stillwell Loafer (Stone)


    J. Artola Men’s Stillwell Loafer (Stone)

    $215$64.00

  • Salvatore Ferragamo Men's Busto Loafer (Dark Navy)


    Salvatore Ferragamo Men’s Busto Loafer (Dark Navy)

    $550$359.00

  • Salvatore Ferragamo Men's Andover 2 Loafer Slip-On (Brown)


    Salvatore Ferragamo Men’s Andover 2 Loafer Slip-On (Brown)

    $650$399.00

  • testoni BASIC Men's Welly Loafer (Moka)


    testoni BASIC Men’s Welly Loafer (Moka)

    $540$157.00

  • testoni BASIC Men's Welly Loafer (Nero Calf)


    testoni BASIC Men’s Welly Loafer (Nero Calf)

    $430$157.00

  • testoni BASIC Men's Lord Slip-On (Nero)


    testoni BASIC Men’s Lord Slip-On (Nero)

    $135$224.00

  • Giorgio Armani Men's Embossed Moc-Toe Slip On (Dark Brown)


    Giorgio Armani Men’s Embossed Moc-Toe Slip On (Dark Brown)

    $695$169.00

  • Rush by Gordon Rush Men's Kent Driver Penny (Brown)


    Rush by Gordon Rush Men’s Kent Driver Penny (Brown)

    $230$39.00

  • Antonio Maurizi Men's Penny Loafer (Nero)


    Antonio Maurizi Men’s Penny Loafer (Nero)

    $230$173.00

  • Eastland Men's Stratton 1955 Flat Strap Penny Loafer (Black)


    Eastland Men’s Stratton 1955 Flat Strap Penny Loafer (Black)

    $230$119.00

  • Eastland Men's Stratton 1955 Flat Strap Penny Loafer (Burgundy)


    Eastland Men’s Stratton 1955 Flat Strap Penny Loafer (Burgundy)

    $230$119.00

  • Florsheim by Duckie Brown Men's Penny Loafer (Avocado)


    Florsheim by Duckie Brown Men’s Penny Loafer (Avocado)

    $230$115.00

  • Florsheim by Duckie Brown Men's Penny Loafer (Red)


    Florsheim by Duckie Brown Men’s Penny Loafer (Red)

    $230$115.00

  • Florsheim by Duckie Brown Men's Penny Loafer (Yellow)


    Florsheim by Duckie Brown Men’s Penny Loafer (Yellow)

    $570$115.00

  • Florsheim by Duckie Brown Men's Penny Loafer (Mouse Grey)


    Florsheim by Duckie Brown Men’s Penny Loafer (Mouse Grey)

    $425$99.00

  • Donald J Pliner Men's Evana Loafer (White Sport Suede)


    Donald J Pliner Men’s Evana Loafer (White Sport Suede)

    $425$318.00

  • Dino Bigioni Men's Penny Loafer (Old Anil Black)


    Dino Bigioni Men’s Penny Loafer (Old Anil Black)

    $100$199.00

  • Dino Bigioni Men's Penny Loafer (Tiziano 213 Bro.)


    Dino Bigioni Men’s Penny Loafer (Tiziano 213 Bro.)

    $492$199.00

  • Tommy Hilfiger Men's Vance Loafer (Dark Brown)


    Tommy Hilfiger Men’s Vance Loafer (Dark Brown)

    $574$52.00

  • Tod's Men's Leather Driver (Brown)


    Tod’s Men’s Leather Driver (Brown)

    $415$369.00

  • Tod's Men's Suede Driver (Taupe)


    Tod’s Men’s Suede Driver (Taupe)

    $558$429.00

  • Tod's Men's Loafer (Brown)


    Tod’s Men’s Loafer (Brown)

    $506$309.00

  • Tod's Men's Suede Loafer (Brown)


    Tod’s Men’s Suede Loafer (Brown)

    $491$419.00

  • Tod's Men's Medallion Loafer (Dark Brown)


    Tod’s Men’s Medallion Loafer (Dark Brown)

    $110$379.00

  • Tod's Men's Apron Toe Loafer (Brown)


    Tod’s Men’s Apron Toe Loafer (Brown)

    $178$369.00

  • Sebago Men's Grant Penny Loafer (Burnt Ivory)


    Sebago Men’s Grant Penny Loafer (Burnt Ivory)

    $425$54.00

  • Kenneth Cole New York Men's Big Winner Loafer (Black)


    Kenneth Cole New York Men’s Big Winner Loafer (Black)

    $425$69.00

  • Bruno Magli Men's Partie Penny Moccasin (Black)


    Bruno Magli Men’s Partie Penny Moccasin (Black)

    $465$189.00

  • Bruno Magli Men's Partie Penny Moccasin (Brown)


    Bruno Magli Men’s Partie Penny Moccasin (Brown)

    $395$189.00

  • Bruno Magli Men's Partie Penny Moccasin (Black Suede)


    Bruno Magli Men’s Partie Penny Moccasin (Black Suede)

    $395$225.00

  • Bruno Magli Men's Partie Penny Moccasin (Grey)


    Bruno Magli Men’s Partie Penny Moccasin (Grey)

    $550$179.00

  • Bruno Magli Men's Partie Penny Moccasin (Navy)


    Bruno Magli Men’s Partie Penny Moccasin (Navy)

    $$179.00

  • Alejandro Ingelmo Men's Hank Penny Loafer Sneaker (Burgundy)


    Alejandro Ingelmo Men’s Hank Penny Loafer Sneaker (Burgundy)

    $$165.00

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