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Penny loafers are the perfect shoe to complement menswear-inspired ensembles or to wear with casual outfits when going around town. Whether you favor a designer pair from Proenza Schouler or comfortable slip-ons from Rockport, shop a large selection of stylish penny loafers on Polyvore! These flat shoes are more structured than ballet flats and ideal for the office. To wear them with a variety of looks and balance the masculine lines of the penny loafer, switch up your trousers with an a-line skirt and tights! Although commonly made with a flat heel, there are stacked heel, wedge and even skinny heel variations.

There’s more to the penny loafer than staid neutrals. The classic shoe has been made over, with brands producing them in metallics, bright colors, prints or with interesting details like perforated accents. From grunge favorite Dr. Martens to on-trend Nine West to preppy staple Sperry Top-Sider, you’ll find styles that are as different as the brands that make them.
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  • Everlane Women's Penny Loafers
    everlane.com
    Everlane Women's Penny Loafers
    Free shipping on all orders with 2+ items.
    Meet Penny. Crafted from Italian leather and modeled on our best-selling Modern Loafer it features a subtly tapered toe and the classic slotted band (once used for storing an emergency payphone penny). Worth every penny-and then some. Women's Penny Loafers by Everlane in Black.
  • Andre Assous Patent Leather Loafer
    lastcall.com
    Andre Assous Patent Leather Loafer
    Extra 30% off women's apparel, handbags, shoes & jewelry
    Andre Assous patent leather penny loafer with tonal stitching. 0.8 flat stacked heel. Almond moc toe. Keeper strap over notched vamp. Slip-on style. Leather lining. Ridged outsole. Made in Spain.
  • LOEWE Women's Crocodile-Stamped Leather Penny Loafers
    barneys.com
    LOEWE Women's Crocodile-Stamped Leather Penny Loafers
    LOEWE's dark brown crocodile-stamped calfskin penny loafers are designed with a black grained leather collapsible heel counter. 0.50\"/15mm heel (approximately). Apron toe. Stacked heel. Leather-wrapped welt. Slips on. Lined with leather. Leather sole. Available in Dark Brown/Black. Made in Italy.
  • Everlane Women's Penny Loafers
    everlane.com
    Everlane Women's Penny Loafers
    Free shipping on all orders with 2+ items.
    Meet Penny. Crafted from Italian leather and modeled on our best-selling Modern Loafer it features a subtly tapered toe and the classic slotted band (once used for storing an emergency payphone penny). Worth every penny-and then some. Women's Penny Loafers by Everlane in Cognac.
  • Pre-owned Chanel CC Penny Loafers
    therealreal.com
    Pre-owned Chanel CC Penny Loafers
    Navy suede Chanel round-toe penny loafers with gold-tone interlocking CC medallion at uppers, contrast stitching and rubber soles.
  • Women's Paul Green Metro Metallic Penny Loafer
    nordstrom.com
    Women's Paul Green Metro Metallic Penny Loafer
    With a gleam to outshine any penny, this metallic-finish leather penny loafer features timeless detailing and an elastic topline to assure a sleek, comfortable fit. Brand: PAUL GREEN. Style Name:Paul Green Metro Metallic Penny Loafer (Women). Style Number: 5301051. Available in stores.
  • Women's Cole Haan 'Pinch' Penny Loafer
    nordstrom.com
    Women's Cole Haan 'Pinch' Penny Loafer
    Cole Haan's classic penny loafer-originally popularized on Ivy League campuses in the '50s, and one of the brand's top-selling styles for decades-is set on a sporty, flexible rubber sole that feels as comfortable as a sneaker. Presented in fresh colors and finishes for a modern look, it features Cole Haan's new crustacean logo-a nod to the line's New England beginnings. Designed with a dual-compound cushioning system for traction and energy return, the go-anywhere style reflects the best of Cole Haan's new Grand.OS ""operating system"": comfort without compromise. Oh, and don't worry, the ""Pinch"" style name was inspired by the cobbler's process, not the fit! Brand: COLE HAAN. Style Name:Cole Haan 'Pinch' Penny Loafer (Women). Style Number: 878842. Available in stores.
  • Rag & Bone Women's Dina Saffiano-Leather Penny Loafers
    barneyswarehouse.com
    Rag & Bone Women's Dina Saffiano-Leather Penny Loafers
    Crafted of black and white saffiano leather, Rag & Bone's Dina penny loafers are trimmed with spazzolato leather and inset at vamp with a British penny. 0.5\"/15mm heel (approximately). Apron toe. Penny inset at keeper strap. Stacked heel. Black spazzolato leather trim. Slips on. Lined with leather. Stitched leather sole. Available in Black/White. Made in Italy.
  • Church's Women's Odessa Penny Loafers
    barneyswarehouse.com
    Church's Women's Odessa Penny Loafers
    Church's white calfskin Odessa penny loafers detailed at vamp with fringe. 0.75\"/20mm heel (approximately). Split apron toe. Raised seam at heel counter. Stacked heel. Stitched welt. Slips on. Leather sole. Available in White. Made in Italy.
  • Pre-owned Prada Leather Penny Loafers
    therealreal.com
    Pre-owned Prada Leather Penny Loafers
    Black leather Prada loafers with semi-pointed toes, penny straps at vamps and grey rubber soles. Includes box and dust bag.
  • G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    macys.com
    G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    A menswear-inspired look in an intriguing variety of tones and color combinations adds spark to your office look in G.h. Bass & Co.'s Weejuns Whitney loafers.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • Cole Haan Pinch Penny Loafer
    nordstromrack.com
    Cole Haan Pinch Penny Loafer
    Free shipping on all orders over $100
    Cole Haan's classic penny loafer--originally popularized on Ivy League campuses in the 1950's, and one of the brand's top-selling styles for decades--is set on a sporty, flexible rubber sole that feels as comfortable as a sneaker. Presented in fresh colors and finishes for a modern look, it features Cole Haan's new crustacean logo--a nod to the line's New England beginnings. Designed with a dual-compound cushioning system for traction and energy return, the go-anywhere style reflects the best of Cole Haan's new Grand.OS operating system: comfort without compromise. Oh, and don't worry, the Pinch style name was inspired by the cobbler's process, not the fit!Sizing: Runs narrow. B=standard width. Round toe. Penny slot vamp. Slip-on. Removable padded insole. Grip sole. Imported
  • Clarks Doraville Nest Penny Loafer - Wide Width Available
    nordstromrack.com
    Clarks Doraville Nest Penny Loafer - Wide Width Available
    Free shipping on all orders over $100
    A moc-stitched toe highlights the classic silhouette of a nubuck penny loafer designed for versatile style and supreme comfort with Clarks CushionPlus technology and an OrthoLite(R) insole.Sizing: True to size. M=standard width, W=wide width. Moc toe. Penny slot vamp. Slip-on style. Removable OrthoLite insole. CushionPlush technology. Breathable leather lining. Textured treads. Imported
  • Cole Haan Pinch Campus Leather Penny Loafers
    saksoff5th.com
    Cole Haan Pinch Campus Leather Penny Loafers
    Timeless design decorated penny slider accent at top Stacked heel, 1" (25mm) Moc toe Leather upper Slip-on style Textile lining and insole Rubber sole Imported. Dir Shoes - Hb - Direct Shoes. Cole Haan. Color: Evergreen. Size: 9.5,11,10,10.5,8,7,7.5,9,8.5.
  • Tod's Leather Moc-Toe Penny Loafers
    saksoff5th.com
    Tod's Leather Moc-Toe Penny Loafers
    Timeless design enhanced with moc-stitch detailing at toe Leather upper Moc toe Slip-on style Leather lining and trim Leather/synthetic sole Padded insole Made in Italy. Dir Shoes - Hb - Classifications Shoes. Tod's. Color: Brown. Size: 40.5 (10.5),35 (5),39.5 (9.5).
  • Pierre Hardy Black Penny Loafers
    ssense.com
    Pierre Hardy Black Penny Loafers
    Free Express Shipping + Returns
    Buffed calfskin flats in black. Pointed toe. Stud detailing in bronze-tone at vamp. Convertible heel. Tonal leather sole. Tonal stitching.
  • Stella McCartney Black Binx Loafers
    ssense.com
    Stella McCartney Black Binx Loafers
    Free Express Shipping + Returns
    Buffed faux-leather platform penny loafers in black. Round toe. Gold-tone curb chain at vamp. Tonal grosgrain trim at collar. White rubber sole. Tonal stitching. Approx. 2 heel, 1.25 platform.Made from cruelty-free, non-animal materials.
  • Everlane Women's Penny Loafers
    everlane.com
    Everlane Women's Penny Loafers
    Free shipping on all orders with 2+ items.
    Meet Penny. Crafted from Italian leather and modeled on our best-selling Modern Loafer it features a subtly tapered toe and the classic slotted band (once used for storing an emergency payphone penny). Worth every penny-and then some. Women's Penny Loafers by Everlane in Oxblood.
  • Marc Joseph New York Greenwich Leather Penny Loafer
    lastcall.com
    Marc Joseph New York Greenwich Leather Penny Loafer
    Extra 30% off women's apparel, handbags, shoes & jewelry
    Marc Joseph New York leather loafer with patent trim. 0.5 flat stacked heel. Round moc toe. Notched vamp. Penny saver strap. Padded footbed. Leather lining. Rubber outsole. Greenwich is made in Brazil.

Want more ideas? Try:

  • Manolo Blahnik Women's Vazca Penny Loafers
    barneys.com
    Manolo Blahnik Women's Vazca Penny Loafers
    Exclusively Ours! Manolo Blahnik black leather Vazca penny loafers are styled with tonal topstitching and leather sole.  0.75"/20mm heel (approximately). . Topstitched moc toe. . Stacked leather heel. Stitched welt. . Tonal topstitching.. Slips on. . Leather sole. . Available in Black. . Made in Italy. .
  • Church's Women's Sally B Spazzolato Leather Penny Loafers
    barneys.com
    Church's Women's Sally B Spazzolato Leather Penny Loafers
    Church's Sally B penny loafers are crafted of black spazzolato leather. 0.75\"/20mm heel (approximately). Split apron toe. Raised seam at heel counter. Stacked heel. Stitched welt. Slips on. Lined with leather. Stitched rubber and leather sole. Available in Black. Made in Italy.
  • Manolo Blahnik Women's Vazca Penny Loafers
    barneys.com
    Manolo Blahnik Women's Vazca Penny Loafers
    Exclusively Ours! Manolo Blahnik dark brown leather Vazca penny loafers are styled with tonal topstitching and a leather sole. 0.75\"/20mm heel (approximately). Topstitched moc toe. Stacked leather heel. Stitched welt. Tonal topstitching. Slips on. Leather sole. Available in Dark Brown. Made in Italy.
  • Manolo Blahnik Women's Vazca Leather Penny Loafers
    barneys.com
    Manolo Blahnik Women's Vazca Leather Penny Loafers
    Manolo Blahnik's Vazca penny loafers are handcrafted of white smooth calfskin. Handmade. 1\"/25mm heel (approximately). Topstitched apron toe. Stacked heel. Stitched welt. Slips on. Leather sole. Available in White. Made in Italy.
  • Pre-owned Bottega Veneta Ponyhair Penny Loafers
    therealreal.com
    Pre-owned Bottega Veneta Ponyhair Penny Loafers
    Navy ponyhair and leather Bottega Veneta round-toe penny loafers with alligator panels at vamps, tonal stitching throughout and stacked heels. Includes box and dust bag.
  • Manolo Blahnik Ellen Watersnake Penny Loafer
    neimanmarcus.com
    Manolo Blahnik Ellen Watersnake Penny Loafer
    Manolo Blahnik watersnake penny loafer. 0.5 flat stacked heel. Round moc toe. Notched vamp with pinked trim. Penny keeper strap. Slip-on style. Smooth sole. Ellen is made in Italy.
  • Burberry Oban Suede Penny Loafer
    neimanmarcus.com
    Burberry Oban Suede Penny Loafer
    Burberry suede loafer. 1 flat stacked heel. Apron toe. Penny saver strap. Notched vamp. Slip-on style. Leather lining. Leather and rubber sole. Oban is made in Italy.
  • Sonia Rykiel Black Embellished Penny Loafers
    avenue32.com
    Sonia Rykiel Black Embellished Penny Loafers
    Sonia Rykiel 's high-impact accessories lend the perfect flourish to after-dark looks. Slip on these black leather loafers for a touch of sparkle, embellished in polished silver-tone eyelets with a faceted jewel penny bar strap. Temper the details with flared culottes and a leather jacket. Black penny loafers with embellishment. Smooth leather. Faceted jewels. Polished silver-tone eyelets. High vamp. Penny strap. Narrow rounded toe. Chunky sole and heels. Storage bag included. Leather linings and sole. 100% leather with strass embellishment. Wipe clean. Made in Morocco.
  • Women's Ara Blanche Loafer
    nordstrom.com
    Women's Ara Blanche Loafer
    A metal charm adds a polished finish to a sleek flat in a classic penny-loafer silhouette, while a comfortably cushioned footbed offers excellent arch support. Brand: ARA. Style Name:Ara Blanche Loafer (Women). Style Number: 5342619. Available in stores.
  • Women's Cole Haan 'Pinch' Penny Loafer
    nordstrom.com
    Women's Cole Haan 'Pinch' Penny Loafer
    Cole Haan's classic penny loafer-originally popularized on Ivy League campuses in the '50s, and one of the brand's top-selling styles for decades-is set on a sporty, flexible rubber sole that feels as comfortable as a sneaker. Presented in fresh colors and finishes for a modern look, it features Cole Haan's new crustacean logo-a nod to the line's New England beginnings. Designed with a dual-compound cushioning system for traction and energy return, the go-anywhere style reflects the best of Cole Haan's new Grand.OS ""operating system"": comfort without compromise. Oh, and don't worry, the ""Pinch"" style name was inspired by the cobbler's process, not the fit! Brand: COLE HAAN. Style Name:Cole Haan 'Pinch' Penny Loafer (Women). Style Number: 878842_8. Available in stores.
  • Women's Hunter Original Waterproof Rubber Penny Loafer
    nordstrom.com
    Women's Hunter Original Waterproof Rubber Penny Loafer
    A classic penny loafer gets a slick, waterproof update with premium Hunter rubber. A cushy footbed, a flexible sole and Hunter's signature grippy calendered tread provide comfort and traction rain or shine. Brand: HUNTER. Style Name:Hunter Original Waterproof Rubber Penny Loafer (Women). Style Number: 5310781. Available in stores.
  • Women's Trotters 'staci' Penny Loafer
    nordstrom.com
    Women's Trotters 'staci' Penny Loafer
    A moc-stitched toe completes the vintage look of a comfortable and versatile penny loafer shaped from rich, pebbled leather. Brand: Trotters. Style Name:Trotters 'staci' Penny Loafer (Women). Style Number: 5187840. Available in stores.
  • Women's Clarks 'Doraville Nest' Penny Loafer
    nordstrom.com
    Women's Clarks 'Doraville Nest' Penny Loafer
    A moc-stitched toe highlights the classic silhouette of a nubuck penny loafer designed for versatile style and supreme comfort with Clarks CushionPlus technology and an OrthoLite insole. Brand: Clarks. Style Name:Clarks 'Doraville Nest' Penny Loafer (Women). Style Number: 5210344. Available in stores.
  • Freda Salvador Kind d'Orsay Penny Loafers
    shopbop.com
    Freda Salvador Kind d'Orsay Penny Loafers
    Luxe croc-embossed Freda Salvador penny loafers in a refined d'orsay silhouette. Petite stud trim at the outsole and a coin accent at the vamp. Partially covered heel and leather sole. Leather: Cowhide. Made in Spain. This item cannot be gift-boxed.
  • Miu Miu Women's Crystal-Embellished Penny Loafers
    barneyswarehouse.com
    Miu Miu Women's Crystal-Embellished Penny Loafers
    Crafted of cognac suede, Miu Miu's penny loafers are styled with an apron toe and crystal-embellished heel.  1.5"/40mm heel (approximately) . Apron toe, stacked heel embellished with square and round white crystals in a goldtone setting . Slips on  . Lined with smooth leather . Leather sole . Available in Cognac . Made in Italy .
  • Prada Women's Penny Loafers
    barneyswarehouse.com
    Prada Women's Penny Loafers
    Prada burgundy burnished spazzolato leather penny loafers styled with a stacked thick heel. 1.5\"/40mm heel (approximately). Apron toe. Stacked thick heel. Slips on. Lined with smooth leather. Leather sole. Available in Granato (burgundy). Made in Italy.
  • Barneys New York Penny Loafers
    barneyswarehouse.com
    Barneys New York Penny Loafers
    Barneys New York brown smooth leather penny loafers. 0.75"/20mm heel (approximately). Topstitched apron toe, stacked heel . Slips on. Suede lining. Leather sole. Available in Brown . Made in Italy.
  • Derek Lam Women's Apron-Toe Penny Loafers
    barneyswarehouse.com
    Derek Lam Women's Apron-Toe Penny Loafers
    Crafted in Italy of black and white spazzolato leather, Derek Lam’s penny loafers are accented with scalloped trim. 1.25\"/30mm heel (approximately). Apron toe. Stacked heel. Slips on. Lined with smooth leather. Leather sole. Available in Black/White. Made in Italy.
  • Barneys New York Women's Suede Penny Loafers
    barneyswarehouse.com
    Barneys New York Women's Suede Penny Loafers
    Barneys New York's apron-toe penny loafers are crafted of dark green suede. 1\"/25mm heel (approximately). Topstitched apron toe. Raised seam at heel counter. Stacked heel. Slips on. Lined with leather. Rubber sole. Available in Military (dark green). Made in Italy.
  • Pre-owned Tod's Leather Penny Loafers
    therealreal.com
    Pre-owned Tod's Leather Penny Loafers
    Walnut leather Tod's Penny loafers with round toes, penny holder accent at uppers and rubber soles.
  • Pre-owned Tod's Leather Penny Loafers
    therealreal.com
    Pre-owned Tod's Leather Penny Loafers
    Burgundy leather Tod's round-toe penny loafers with tonal stitching, covered heels and rubber soles.
  • Pre-owned Ralph Lauren Purple Label Leather Penny Loafers
    therealreal.com
    Pre-owned Ralph Lauren Purple Label Leather Penny Loafers
    Tan leather Ralph Lauren Purple Label penny loafers with round toes, penny holder at uppers and stacked heels.
  • Pre-owned Tod's Leather Penny Loafers
    therealreal.com
    Pre-owned Tod's Leather Penny Loafers
    Creme leather Tod's pointed-toe penny loafers with tonal stitching throughout, enamel penny strap accents at vamps and rubber bumpers at counters and soles.
  • Pre-owned Gianvito Rossi Patent Leather Pointed-Toe Penny Loafers
    therealreal.com
    Pre-owned Gianvito Rossi Patent Leather Pointed-Toe Penny Loafers
    Taupe leather Gianvito Rossi pointed-toe penny loafers with tonal stitching throughout and stacked heels.
  • FitFlop F-Sporty™ Patent Penny Loafers
    fitflop.com
    FitFlop F-Sporty™ Patent Penny Loafers
    Preppy-perfect and gorgeously glossy , introducing our fabulous penny loafers (and the girl who wears them!). Throw a pair on with high-hemmed pants and an oversized sweater and you?re done, polished, totally pulled together. Superversatile, cush underfoot ultra-light and worth every penny!
  • FitFlop F-Sporty™ Felt Penny Loafers
    fitflop.com
    FitFlop F-Sporty™ Felt Penny Loafers
    Preppy-perfect and fabulously fun, introducing our fabulous felt penny loafers (and the girl who wears them!). Throw a pair on with high-hemmed trousers and an oversized jumper and you're done, polished, totally pulled together. Superversatile, cush underfoot ultra-light and worth every penny!
  • FitFlop F-Sporty™ Felt Penny Loafers
    fitflop.com
    FitFlop F-Sporty™ Felt Penny Loafers
    Preppy-perfect and fabulously fun, introducing our fabulous felt penny loafers (and the girl who wears them!). Throw a pair on with high-hemmed trousers and an oversized jumper and you're done, polished, totally pulled together. Superversatile, cush underfoot ultra-light and worth every penny!
  • Marc Joseph New York East Village Penny Loafers
    macys.com
    Marc Joseph New York East Village Penny Loafers
    Classic penny loafer styling in patent leather with hand crafted attention to detail makes these East Village flats from Marc Joseph a must-have office look.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Add a vibrant pop of purple to your everyday look in an updated classic penny loafer design with Cole Haan's comfy go-to Pinch Weekender flats.
  • G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    macys.com
    G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    A menswear-inspired look in an intriguing variety of tones and color combinations adds spark to your office look in G.h. Bass & Co.'s Weejuns Whitney loafers.
  • Tommy Hilfiger Women's Butter Penny Loafers
    macys.com
    Tommy Hilfiger Women's Butter Penny Loafers
    Tommy Hilfiger's Butter loafers feature classic penny loafer styling in a variety of sophisticated color schemes for an office look with distinction.
  • G.h. Bass & Co. Women's Weejuns Willow Penny Loafers
    macys.com
    G.h. Bass & Co. Women's Weejuns Willow Penny Loafers
    G.h. Bass & Co. updates a classic with a cluster of playful tassels in the Weejuns Willow penny loafers.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • Cole Haan Pinch Weekender Slip-On Loafers
    macys.com
    Cole Haan Pinch Weekender Slip-On Loafers
    Cole Haan keeps off-day fashion classic-chic in the tasteful Weekender penny loafers–a great look with Bermuda shorts.
  • G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    macys.com
    G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    A menswear-inspired look in an intriguing variety of tones and color combinations adds spark to your office look in G.h. Bass & Co.'s Weejuns Whitney loafers.
  • Tommy Hilfiger Women's Butter Penny Loafers
    macys.com
    Tommy Hilfiger Women's Butter Penny Loafers
    Tommy Hilfiger's Butter loafers feature classic penny loafer styling in a variety of sophisticated color schemes for an office look with distinction.
  • G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    macys.com
    G.h. Bass & Co. Women's Weejuns Whitney Penny Loafers
    A menswear-inspired look in an intriguing variety of tones and color combinations adds spark to your office look in G.h. Bass & Co.'s Weejuns Whitney loafers.
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