In the daytime, Hugh Hefner wore custom-made silk — not satin, satin made him slip off the bedsheets, he said — in a shade he liked to call “gunfighter black.” At night he would transition into rich colors. Of an evening, he would add a bathrobe. For company, he’d put on a smoking jacket.
Mr. Hefner said that he did not wear underwear.
He moved his office to the bedroom in 1963, a decade after the first issue of Playboy, and never looked back. “One of the key moments in my life was the discovery that I could get away with wearing pajamas most of the time,” Mr. Hefner wrote in “Hef’s Little Black Book,” his sort-of memoir from 2004.
In 1974, he moved to California from Chicago for good as well. He told People magazine that in those intervening 11 years, he “never went out of the house” — so it was only in his new life in Los Angeles that he began to show off his vast collection of sleepwear outdoors. (Plenty of people in Chicago made it indoors though: During the 1968 Democratic National Convention, Mr. Hefner’s weeklong party found him in “blue and red print batik pajamas with an olive green bathrobe,” according to a New York Times report.)
Like so many in California, Mr. Hefner entered an endless cycle of party, rinse, repeat. In an essay comparing the “heterosexually omnipotent, but increasingly prosthetic” manhood of the fictional James Bond and the very real Hugh Hefner, Patrick O’Donnell, the academic, describes Mr. Hefner’s schedule as he exhibited it in the 1980s as one without end: “Each ‘evening’ begins precisely at the same time; each night of the week is dedicated to a different purpose: Monday is new movie night, Wednesday is poker night with the boys, Friday is party night, Sunday is vintage movie night, etc.”
In recent years he still had the kind of schedule that a particularly anxious adolescent would find comforting. Wednesdays and Fridays, Mr. Hefner and his entourage would make the round of the clubs, and then, according to a memoir from his ex-girlfriend Holly Madison, would retire to chambers. (There, all the “girls” would change into pajamas — flannel for them, not silk, she said.)
“It was always exactly the same because that’s just how he likes to live his life,” Ms. Madison told BuzzFeed in 2015.
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