RIP Hugh Hefner, Inventor of Pajama Dressing: A Style Appreciation

Hugh Hefner and Cooper Hefner -Annual Midsummer Night's Dream Party - Getty- H 2017
Christopher Polk/Getty Images for Playboy

Hugh Hefner and Cooper Hefner

Farewell to an icon of men's style for 60 years.

Hugh Hefner, founder of Playboy Enterprises, died at age 91 on Wednesday. No doubt he was a journalism pioneer, a free speech advocate and a sexual trailblazer. But he was also a men's style icon.

The original pajama dresser, he was wearing silks and robes during the daytime long before fashion daredevil Jared Leto was a glimmer in his mama's eye, or Gucci designer Alessandro Michele put us all in furry-lined slippers. Hef also understood the branding power in crafting a signature look, whether that was the corseted, fluffy-tailed Playboy bunnies that embodied his empire from its beginnings in Chicago, or his own.

And in the late 1990s, Playboy, the brand that made its name by getting women to take it all off, launched licensed clothing and accessories of its own, now available worldwide and online.

He told the Daily Mail in a lengthy sartorial treatise on his personal style in 2007 that he owned 200 pairs of silk pajamas, which he wore every day along with black velvet slippers by the now-shuttered Di Fabrizio of Hollywood on Fairfax Avenue, the self-professed "shoemaker to the stars" whose first client was Dean Martin and whose legacy lives on in the family-owned Pasquale's Shoe Repair on San Vicente. Loungewear has since become its own fashion category, thanks to brands like Juicy Couture, and pajama dressing has reached the highest echelons of luxury, seen on the runways at Michael Kors and Prada.

Hef's elegant style owed a lot to the Rat Pack, and the way those guys always dressed for themselves as much as the ladies. Over the years, he bought clothes at Sy Devore, the legendary Hollywood haberdashery that catered to Frank Sinatra and others. But in more recent years, he had all of his suits custom made by Giorgio Armani, he told the Daily Mail. His favorite outfit was a custom made smoking jacket and pajamas — "black during the day — black is serious, for taking care of business."

His best shirts "look like they are from the '20s and '30s," he added, and were made by local fashion designer and friend Rick Pallack, based in Sherman Oaks, who has been catering to the Hollywood industry since the 1980s, and over the years has provided tuxedos for Oscars broadcasts, the L.A. Lakers and more.

But bigger than all those names, even Armani's maybe, is Playboy's. Through licensing agreements, the Playboy brand now appears on a wide range of consumer products in more than 180 countries, as well as retail stores and entertainment venues. 

At the Playboyshop you can buy throwback, cropped Playboy logo T-shirts for ladies, and hip bomber jackets for men, but sadly, no elegant PJs or smoking jackets that nod to Hef's own style, at least not yet. I'm also betting next season's men’s runways will be full of them.