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
Gucci, $495; gucci.com for stores.