Instant Classic: The Loafer

Make like a smooth criminal in polished slip-ons, upgraded with luxe patent and reptile finishes.

kate moss
Make like a smooth criminal in polished slip-ons, upgraded with luxe patent and reptile finishes.
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Flat-Out Sexy

They may have moonwalked on MTV, but these old-school flats were a wardrobe staple long before the King of Pop trademarked his black-and-white pair. Originally worn by Norwegian cattle farmers in the 1930s, moccasin-style shoes moved West with designer flourishes in the 1950s and '60s: G.H. Bass' penny slot and Gucci's horse bit pushed the style further from its simple origins. Today's pairs come slimmed down and buffed to a high-wattage shine, and can be spotted on casual-cool undergrads and street-style stars. Top with skinny suit and just beat it.

The way they wore: Kate Moss in London, 2009

Niki Nikolova/Filmmagic
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Flat-Out Sexy

Gucci, $495; gucci.com for stores.

Richard Majchrzak/Studio D
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Flat-Out Sexy

Coach, $188; coach.com.

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Flat-Out Sexy

Yves Saint Laurent, price upon request; (212) 980-2970.

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Flat-Out Sexy
Grace Kelly, 1955
Paramount Pictures/Courtesy Neal Peters Collection
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Flat-Out Sexy

ChloƩ, $795 at Iris; (212) 645-0950.

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Flat-Out Sexy
Tod's, $625; (800) 457-TODS
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Flat-Out Sexy

Louis Vuitton, $985; (866) VUITTON.

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