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]. 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.

I wear custom Armani suits but they have cuffs. I’m the only guy in town that has Armani’s with cuffs, that is simply a tip of a hat to the fashion of my [time].

There was a point in the later 1960’s in which I actually designed my own wardrobe.

[The watch is] a gift from my former wife. I keep a scrapbook, which I started in high school that now has about 2500 volumes. I’m in the Guinness Book of Records with the longest, largest scrapbook of anybody in the world.

Yeah, velvet is a big fabric for me.

We celebrate my birthday weekend in April by running Casablanca every year. My friends and I all dress in the style of Casablanca, so I wear the white tuxedo jacket and bow tie. It’s a very romantic night, we watch the movie, we know it line for line, but it’s a night that all my friends really look forward to. After the movie we go across the hall to the dining room, which has been converted into Rick’s Café American, where we have champagne and caviar by candlelight. It’s very romantic.

In social settings, I found myself perfectly comfortable in pajamas, and then it reached a point frankly where people were disappointed if I wasn’t wearing pajamas. It became something that represented the lifestyle.

[The sailor hat came along] sometime in the last decade. 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!

This is an exact replica of Hef’s Hollywood Walk of Fame star, located next to the Roosevelt Hotel in Hollywood. He received the honor for his 1950s “Playboy’s Penthouse” and 1960s “Playboy After Dark,” both ground breaking television variety shows featuring top celebrities, athletes and writers in a casual, party-like setting.

This building houses Playboy pinball machines, classic, full-size arcade games including Pac-Man, Donkey Kong, Frogger and Centipede as well as new, state-of-the-art machines, plus foosball, pool and poker tables.

The structure is filled with nostalgic pieces of artwork, gifts and neon lights that honor Hef and Playboy.

I am essentially a very romantic fellow.

In the early 1970s, Hef’s girlfriend Barbi Benton stumbled upon this amazing 5.7 acre estate. Although it did not have many of the amenities found today, Hef quickly fell in love with the property. When Playboy purchased it in 1971 for $1.05 million, it was the largest residential real estate transaction in Los Angeles history.