Hugh Hefner is one of those rare individuals that appears to exist in a universe all his own. Sure, there’s the physical “universe” of the Mansion, the Bunnies, and the never-ending party that is Playboy, but there’s also something much deeper. Hefner has made a career out of the sort of images that you wouldn’t want your boss, girlfriend, mother, or fellow straphanger to catch you looking at, and yet, Hef still manages to come across as a gentleman at every turn. Of course, there is something slightly off about a nearly-ninety year old man that wears robes in public and is married to a women sixty years his junior, which is why we prefer to remember Hef for his younger, more presentable years.

Unlike Handi-cam creeps and even his contemporary, Larry Flynt, Hugh Hefner understood that to deal in “mature” images, one should also appear mature. Playboy launched in 1953, and throughout the subsequent decade or so, Hefner always dressed not like some free-wheeling philanderer, but like a reputable businessman. He dressed in natty suits, slim ties, and shivering break trousers, puffing continuously on his signature sloping “S” pipe.

If you saw Hugh Hefner on his way to work in the fifties or sixties, you would think he was just any other Midtown Manhattan businessman bound for the office. It just so happened that waiting at Hefner’s office were photos of naked women for his approval. The women he profiled might not have kept their clothes on, but clothes were paramount to Hefner’s personal image and the early success of Playboy. Had Hefner appeared like some disheveled smut peddler, Playboy never would’ve earned the mainstream acceptance that it needed to blossom into major publication. Thanks in part to Hefner’s traddy attire and collected disposition, Playboy sat comfortably alongside Esquire, Vanity Fair, and GQ as a sophisticated entity with a bold, raffish streak. Just like their editor in chief.