Hugh Hefner

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Hugh Hefner at the premiere of Sylvester Stallone's movie F.
Hugh Hefner at the premiere of Sylvester Stallone's movie F.Photography by Alan Light

This autumn/winter Tom Ford’s collection for men comprised of suits and robe-like dinner jackets in luxe crushed velvet textures, bow ties and velvet bows on slipper-esque shoes. The retro element in some ways echoed styles seen in his 60s-set

This autumn/winter Tom Ford’s collection for men comprised of suits and robe-like dinner jackets in luxe crushed velvet textures, bow ties and velvet bows on slipper-esque shoes. The retro element in some ways echoed styles seen in his 60s-set feature film A Single Man, but the luxury element was turned up a notch – so much so that comparisons can be drawn with someone else whose look and lifestyle was born out of the same era, a certain Hugh Hefner.

Hefner’s image, so intrinsically linked to the Playboy lifestyle, wasn’t in evidence at the initial conception of Playboy magazine in 1953. It was seven years later that he found his look. In a book compiled by the Chicago Sun Times entitled 20th Century Chicago, 100 Years, 100 Voices, Hefner talks about the significance of the year 1960 as a turning point for not just his sartorial choices but his entire lifestyle. “It was the year I came out from behind my desk and started living the life exposed in the magazine – smoking the pipe, wearing the smoking jacket, driving a Mercedes Benz 300SL.”

The silk charmeuse pyjamas Hefner likes to lounge in are custom-made by a local tailor, Richard Brown, who also makes the flannel pyjamas he sleeps in. His iconic smoking jacket is also bespoke and for formal occasions he likes an Armani suit and Turnbull & Asser shirts. His famous slippers are by Los Angeles-based “shoe-maker to the stars” Pasquale Di Fabrizio. Hefner’s retro style is much more than a fetish for old Hollywood glamour but symbolic of his passion for actively preserving historical Hollywood like a sort of renegade National Trust for American cultural history. In April of this year he donated $900,000 to close the gap in a $12.5 million fund-raising drive to save the Hollywood sign from development. He also funds the restoration and digitisation of old film from the golden age of early Hollywood.

As trends bubble up, burst and fade, Tom Ford may revisit 60s style for a season, the television series Mad Men may continue to inspire men to up their sartorial game, but the true purveyor of the era's style, the man whose passion for Hollywood glamour not only informs his style choices but permeates his entire lifestyle, is Hugh Hefner.

Text by Laura Havlin