Year It First Dropped: 2012

For years, companies have tried (and failed) to make a hybrid sneaker/dress shoe. Chicago's Cole Haan had been doing it well since 2000, incorporating Nike Air technology into loafers, brogues, and boots, but it did so surreptitiously—hiding all the tech underneath. When they had the bright idea to incorporate a Lunar sole on a dress shoe upper, they created the perfect balance of sneakerhead and menswear nerd. The Lunargrand Wingtip was the footwear equivalent of the guy who wears a perfectly-fitting suit with statement sneakers—classy yet self-aware, but definitely not overdone. And when you add a third cook in the kitchen, Hiroshi Fujiwara's FRAGMENT design, they went from awesome innovation to must-have item. Bright contrast soles were already having a moment, so combining them with lesser seen silhouettes like kiltie loafers and saddle shoes and luxe textures like pebbled leather not only made them cooler, it made them even more covetable.