‘I was Hugh Hefner’s girlfriend – red lipstick was banned for creepy reason’

Playboy boss Hugh Hefner controlled every aspect of his “girlfriends’” lives, from who they met, to how much they drank. His strict rules even extended to their makeup – for a very creepy reason.

Speaking on the Coco Mocoe podcast, Holly Madison – at one point the elderly playboy’s “Number One” girlfriend, said he wanted all the women around him to look “barely legal”. Hefner thought red lipstick made women look “old” because it reminded him of the sophisticated fashion models he’d see in magazines as a young man.

“It was a lot of fabric and big skirts and everything, and he hated that,” Holly said. “He wanted skimpy and fresh-faced and very young looking”. She added that she thought the red lipstick ban was a “control tactic” that Hefner would use to keep his “girlfriends” in line.

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“He felt like he had the leeway to yell at me over it,” Holly recalled. “I think it was a control tactic, but also, when I was brand new, I wore red lipstick out a couple of times, and he didn't say anything about it, because when you were the new girl in the group, you were always treated well”.

But that changed when she was fully brought into the Playboy “cult”. Holly explained, “Somebody said, like, the higher up you are in a cult the worse you're treated because they want the new people to want to bond and feel into it".

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“So," she went on, "I would wear red lipstick when I was new, it wasn't a big deal. It wasn't a big deal until six months into it, when I was living in his bedroom, and I was the main girlfriend, then he felt like he had the leeway to yell at me over it”.

Holly was 21 when she started dating Hefner, who was 75 at the time. She said he always wanted women to look young and fresh-faced. "So I think that’s where his hatred of red lipstick came from," she added. Strong Fifties-style red lips and heavy makeup made Hefner think of “an older mature woman,” Holly says, and it wasn’t the barely legal thing any more."

Long blonde hair was also a must for Hefner. When Holly arrived at the fabled Playboy mansion and realise start everyone looked like her she decided to have her hair cut shorter in order to stand out. It didn’t go well. "I came back with short hair and he flipped out on me," she said, "and he was screaming at me and said it made me look old, hard and cheap."

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