American icon and billionaire founder of the Playboy Mansion Hugh Hefner has died at the age of 91. He became the ultimate poster boy for his rakish life in loungewear.
He owned around 200 silk pyjamas, a uniform he wore every day at the Mansion surrounded by his Playmates.
Hefner's signature look was the black-lined, red velour smoking jacket worn over silk pyjamas.
Style of an icon
But while he sexed up loungewear and reportedly spent more than 12 hours a day in bed (watching TV and doing other things), there was a time Hefner ruled the style stakes beyond bedroom attire.
In 1979 he wore double denim before it became a cool thing – what's more rollerskating with a Playboy model in skimpy gear at a party he hosted. He would be spotted at airports and in meetings wearing a fitted sport coat and tapered pants with a black bow tie while on other 70s occasions he donned a three-piece checkered brown suit with a white shirt – ever stylish, a hint of sleaze and plenty of credibility and cash flow to match.
If he had to get dressed for any other occasion, you'd find him in an Armani custom-made suit – he owned more than 300 of them and always liked his hemlines cuffed.
He once told the press he only wore black pyjamas when he had to 'take care of business' otherwise you'd spot him wearing red, fuscia pink and bottle green over the decades.
Hefner loved his smoking slippers. His preferred go-to label for all 12 pairs of black loafers in his closet was Di Fabrizio Shoes of Hollywood - the self-billed 'shoemaker to the stars' – who claims his first client was Dean Martin and also made dancing shoes for Michael Jackson.
His most flamboyant style era was the '70s – Hefner wearing wide collared paisley open buttoned shirts under flared black velvet suits while a three piece white suit matched with a red shirt was worn at Playboy's 25th anniversary. He was Saturday Night Fever meets pimp style at once.
He wore a pair of black bunny ears on Saturday Night Live in the '70s with his Playboy Playmates and dabbled in corduroy jackets too, but he'll always be remembered as the granddaddy of sleaze where women were his ultimate accessory and he wouldn't go anywhere without his signature sailor hat and smoking pipe.
The Chicago native, who started Playboy magazine in the '50s, was known for hosting lavish parties and in the '60s that included all the cool entertainers from Tony Bennett to Sammy Davis Jr.
Check out the gallery above to see some of Hefner's most memorable looks.