In 1961, Lance Clark—one of the heirs to the Clark shoe company in England—sketched out an unadorned hand-sewn shoe design inspired by a suede Sioux moccasin that had caught his attention. He then had the sketch developed into a prototype at the Padmore & Barnes factory in Ireland. Four years later, the Wallabee, as it would soon come to be known, was released in 1965. Built on a "nature-formed last" that allows for natural toe spread, it's one of the most comfortable boots you'll ever pull on. Not to mention, they're the perfect accompaniment to fall's rugged chinos, broken-in denim and corduroys. And while the signature plantation crepe sole and simple moccasin construction remain, the unlined leather uppers now come in nearly a dozen shades and styles. But we're partial to the timeless cola-colored suede.