How Playboy Mogul Hugh Hefner Made Smoking Jackets & Slippers Cool

Halloween is just around the corner, and it’s likely Hugh Hefner lookalikes will be out in full force dressed no doubt in his signature smoking jacket and smoking slippers. It’s a fitting fashion tribute to the Playboy magazine founder who died today at the age of 91. It’s a look that’s become as iconic as the Playboy bunny suit.

Hefner’s suave loungewear style stood for a man who no longer was required to work but could simply spend the day in bed — having amassed a fortune estimated today at $50 million. And while that type of lifestyle is not an option for most men, it certainly is something to aspire to.

Anna Berglund, Hugh Hefner and Crystal HarrisKandyland V Benefit at the Playboy Mansion, Beverly Hills, Los Angeles, America - 27 Jun 2010 Anna Berglund, Hugh Hefner and Crystal Harris at Kandyland V Benefit at the Playboy Mansion, Beverly Hills, June 27, 2010. BDG/REX/Shutterstock

Hugh Hefner, of course, didn’t need to buy ready-made shoes. According to fashion insiders, his footwear was custom-made by the now-defunct Di Fabrizio of Hollywood — always in go-with-everything black velvet.

While the media mogul reigned in the the ’60s and ’70s as a barometer of cool, even as he began aging, he continued to hold a top spot as one to watch when it came to good dressing.

But while Hefner was stepping into a pair of handmade shoes, he was also licensing his name to a line of more moderately priced footwear made in the Far East. In fact, these retro looks can be snagged on eBay today. But you better hurry up while supplies last.

Click through the gallery to see Hugh Hefner’s style through the years.