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Penny Loafers

Shoes make the outfit! From round to pointy-toe picks, amp up casual looks with classic penny loafers. Check out brands like Aerosoles, COACH, Cole Haan, Lauren Ralph Lauren and MICHAEL Michael Kors.

Chic Flats
Infuse your everyday looks with a little sophistication. Casual shoes like penny loafers are perfect. Dress up a t-shirt and jeans or pretty sundress with the adorable shoe. Pile on silver bracelets for a cool look.

Perfect for the Office
Complete your office ensemble with a pair of penny loafers. Stand out in rich brown or black picks featuring delicate details and modern styles. Ready for a quick shoe update? Shop penny loafers from your favorite brands at Macy’s.

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  • 213 items in Penny Loafers

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    • 2 colors
      Tommy Hilfiger Men's Axtons Drivers, Created For Macy's
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      $70.00
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    • 3 colors
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      Tommy Hilfiger Men's Dathan Driver
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      $70.00
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      (134)
    • 2 colors
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      Clarks Men's Tilden Free Loafer
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      $90.00
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      (108)
    • 2 colors
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      Clarks Men's Cotrell Step Bike Toe Slip On
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      $90.00
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      (127)
    • 2 colors
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      Stacy Adams Men's Beau Bit Perforated Loafer
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      $90.00
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      (146)
    • 2 colors
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      Alfani Men's Len Driver with Bit, Created for Macy's
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      $79.99
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      (62)
    • 4 colors
      Alfani Men's Sawyer Slip-On Loafers, Created for Macy's
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      $79.99
      Sale $39.93 - 39.99
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      (39)
    • 2 colors
      Lightweight
      Rockport Men’s Style Leader 2 Bike Toe Slip On Loafers
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      $110.00
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      (84)
    • 2 colors
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      Rockport Men's Classic Penny Loafer
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      $120.00
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      (181)
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      Calvin Klein Men's Bernard Tuxedo Shoes
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      $110.00
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      (53)
    • Lightweight
      Ecco Men's Helsinki Comfort Loafers
      $150.00
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      (342)
    • 2 colors
      Extended Widths
      Alfani Men's James Suede Driver with Bit, Created for Macy's
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      $79.99
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      (107)
    • 2 colors
      Extended Widths
      Clarks Men's Escalade Step Loafer
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      $90.00
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      (181)
    • 3 colors
      Cole Haan Men's Pinch Weekender Slip-Ons
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      $90.00
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      (7)
    • 2 colors
      Unlisted by Kenneth Cole Men's Stay Bit Loafers
      Limited-Time Special
      $75.00
      Sale $36.99
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      (4)
    • 3 colors
      Extended Widths
      Calvin Klein Men's Magnus Driver
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      $130.00
      Sale $64.99
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      (46)
    • 2 colors
      Alfani Men's Blaine Penny Loafers, Created for Macy's
      Limited-Time Special
      $109.99
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    • 2 colors
      Clarks Men's Tilden Way Leather Penny Loafers
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      $90.00
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      (7)
    • 3 colors
      Polo Ralph Lauren Men's Wynding Driver
      $99.00
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      (59)
    • 2 colors
      Kenneth Cole Reaction Men's Design 20724
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      $120.00
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      (18)
    • 3 colors
      Alfani Men's Marcus Tumbled Drivers, Created for Macy's
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      $79.99
      Sale $39.93 - 39.99
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      (23)
    • 3 colors
      Sperry Men's Hampden Venetian Loafer
      $100.00
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      (44)
    • 2 colors
      Polo Ralph Lauren Men's Woodley Venetian Driver
      $100.00
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      (31)
    • 2 colors
      Extended Widths
      Cole Haan Men's Tucker Venetian Loafers
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      $150.00
      Sale $99.99
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      (44)
    • 4 colors
      Calvin Klein Men's Madsen Embossed Tumbled Leather Drivers
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      $130.00
      Sale $77.99
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    • 4 colors