Examining Hugh Hefner's Style: How the Playboy Founder Made Pajama Dressing a Force in Fashion

American icon was known for wearing robes and other lounge wear inside the Playboy Mansion

By Mike Vulpo Sep 29, 2017 12:35 AMTags

Hugh Hefner knew how to turn heads and sometimes it was solely because of his outfits.

As the tributes and memories continue to pour in from Hollywood, Playboy models and Girls Next Door cast members, some fans of the American icon are celebrating the fashionable looks seen on Hugh.

Whether he was lounging at the Playboy Mansion or working hard on an issue of Playboy magazine, Hugh helped pave the way for pajama dressing.

"My favorite outfit consists of pajamas and a custom-made smoking jacket," Hugh once shared with the Daily Mail back in 2007. "I have 200 pairs of silk pajamas. I always wear black during the day – black is serious, for taking care of business."

He added, "Silk against skin is very sensual. You have no idea how comfortable it is to lie around wearing pajamas."

Hugh Hefner: A Life in Pictures
Charley Gallay/Getty Images for Playboy

Hugh would also reveal to the outlet that he didn't have a stylist. Instead, he chose all his clothes and shoes and had "absolutely no idea how much anything costs."

"The fact that I wear sleepwear evolved early on—I started the magazine in 1953—found myself working at night, around the clock, and then got the first mansion in Chicago [in 1953]," he once shared via Coveteur. "The plan was if I had the mansion to go to I wouldn't be working quite so much, but the reality is I found myself taking the work with me and I started working out of the mansion—much of it at night—and it just became a natural kind of thing to wear the pajamas, they were comfortable."

While we're not sure if Hugh deserves all the credit, loungewear has since become its own fashion category while pajama dressing has reached a whole new level of luxury with brands like Michael Kors and Prada sporting looks on the runway.

Hugh Hefner's Movie and TV Cameos
AP Photo/Kevork Djansezian

That's not to say everything Hugh wore was related to pajama dressing. The magazine editor was a fan of wearing custom Armani suits with cuffs. In the late 1960's, he admitted to designing his own wardrobe. And then there's the sailor hat that is easily recognizable from photo shoots and red carpets.

"I was spending more time outside, here, and as the hair began to become more unruly and less of it, it was just easier to put on the cap than worry about the hair!" Hugh admitted.

As the Hollywood Reporter rightfully pointed out, Hugh's fashion sense only continued through the Playboyshop. The online website continues to thrive thanks to the signature Playboy logo that Hugh supported for so many years.

And while pajamas may not be available on the site just yet, it will likely serve as a symbol to the Playboy lifestyle for many years to come.

"One of the key moments in my life was the discovery that I could get away with wearing pajamas most of the time," Hugh wrote in Hef's Little Black Book.

As they like to say, the clothes always make the man.

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