This Is The Apparent Reason Why Hugh Hefner Wouldn’t Let His Playboy Playmates Wear Red Lipstick

Holly Madison was just 21 years old when she moved into the Playboy Mansion back in August 2001, and she is thought to have started dating Hugh Hefner that same year — when he was 75.

Holly Madison hugging Hugh Hefner as he kisses her on the cheek
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In case you somehow didn’t know, Hugh had multiple girlfriends that were several decades his junior living with him at the infamous mansion at any one time.

Hugh Hefner sitting on a couch with his three girlfriends
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He had sexual relationships with all of them simultaneously, and the woman he chose to be his “main girlfriend” changed constantly.

Hugh posing for a photo with Holly Madison and another woman. Both women are wearing the playboy bunny outfit
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Holly quickly became Hugh’s main girlfriend after she moved in, and they didn’t split until 2008. Holly later described their relationship as “very Stockholm syndrome.

Closeup of Holly Madison
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And in recent years, Holly has been incredibly vocal about her negative experiences at the mansion, and has recounted several problematic encounters with Hugh.

Closeup of Holly and Hugh
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On her and fellow ex-playmate Bridget Marquardt’s podcast, Girls Next Level, Holly said that Hugh would use baby oil as lube against her will, and that she was ordered to have sex with him while under the influence.

Holly, who is holding a small dog, standing next to Hugh
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Then in the 2021 docuseries Secrets of Playboy, Bridget admitted that Hugh would be “pretty abrasive” in the way that he spoke to Holly.

Bridget and Holly holding each other as they smile for a photo
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Recalling one instance in particular, Bridget said: “[Holly] came down with red lipstick one time, and he flipped out and said he hated red lipstick on girls [and to] take it off right away, even though other people could wear red lipstick, and it didn’t seem to bother him.”

A closeup of Holly wearing red lipstick on the red carpet
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And Holly shed fresh light on Hugh’s hatred of red lipstick in a recent appearance on Coco Mocoe’s podcast, Ahead of the Curve.

Holly sitting on a couch during her interview for Bridget's podcast
YouTube @CocoMocoe / Via

Speaking to the former playmate, host Coco said: “Hugh Hefner hated red lipstick. Do you know where that stemmed from, or do you think it was a control tactic?”

Hugh Hefner smiling for a photo while wearing his robe
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Holly began her response by saying that girls that were new to the mansion would be allowed to wear red lipstick without any repercussions, seemingly supporting what Bridget had said two years earlier.

Closeup of Holly
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“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,” she shared. “Because when you were the new girl in the group, you were always treated well.”

Closeup of Holly
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Remembering a quote that she’d heard elsewhere, Holly continued: “Somebody said, like, the higher up you are in a cult the worse you’re treated because they want the new people to bond and feel into it.”

Hugh Hefner at a club surrounded by several women
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“So I would wear red lipstick when I was new, and it wasn’t a big deal until, like, six months into it, when I was living in his bedroom and I was the main girlfriend, and he felt like he had the leeway to yell at me over it,” she said.

Closeup of Hugh and Holly
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Theorizing as to why Hugh had an issue with the bold makeup look, Holly added: “I think he didn’t love it because when he invented the concept of a playmate in the ’50s, he wanted the women to look very young and fresh-faced because he felt like the look in the ‘50s at the time was very… He described it as 'somebody’s older sister.'”

Holly and Coco in conversation
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“It was more sophisticated, fashion model, red lipstick,” she explained. “It was a lot of fabric and big skirts and everything, and he hated that. He wanted skimpy and fresh-faced and very young looking.”

Hugh with Playboy bunnies
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“So I think that’s where his hatred of red lipstick came from,” Holly concluded. “That was an older mature woman, and it wasn’t, like, the barely legal thing anymore.”


Watch the @hollymadison interview on YouTube today at 1 pm or listen on podcast Monday morning ❤️🎧 #AheadOfTheCurve #HollyMadison #Podcast #HughHefner

♬ original sound - Coco Mocoe

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And this certainly isn’t the first time that Holly has opened up about Hugh’s apparent desire for his Playboy playmates to look young.

Hugh with Playboy playmates
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Speaking on Trisha Paytas’s podcast Just Trish last month, Holly said that the beauty standards at the mansion revolved around looking as thin and young as possible. She added that Hugh “liked his women very, very thin.”

Closeup of Hugh and Playboy playmates
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And in 2021, Holly recalled Hugh angrily chastising her for cutting her hair short because he felt that it aged her.

Closeup of Holly
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“My hair was really long naturally, and I was just like, ‘I’m gonna go chop my hair off so I can at least look a little different,'” she said. “I came back with short hair, and [Hugh] flipped out on me. He was screaming at me and said it made me look old, hard, and cheap.”

Holly smiling and rocking a short bob haircut
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Hugh died in 2017 at 91 years old.

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