Hugh Hefner Wouldn’t Let Playboy Models Wear Red Lipstick —His Reason Is Even More Disturbing

Trigger Warning: This article contains themes of suicide and sexual assault that some readers may find distressing.

Hugh Hefner had some strange rules for the women who lived in his mansion. One of these restrictions concerned lipstick, particularly in the red shade. The famous founder of Playboy magazine didn't want his models wearing red lipstick because Hefner had a specific image in mind for his models: he wanted them to look innocent and youthful. In his mind, red lipstick made women look older and more sophisticated, as per Holly Madison, who dated Hefner for seven years and lived in the Playboy Mansion from 2001 to 2008. 

Madison said that the lipstick rule wasn't obvious at first. As per E! News, she could wear red lipstick without any problems when she was new to the mansion: "...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 things changed over time, and she even called it a 'control tactic.'

"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 that he felt like he had the leeway to yell at me over it," Madison explained in the episode of the Ahead of the Curve podcast. She also explained how steering clear of red lipstick was about keeping the models looking young. She said, "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." Madison explained Hefner's view: "To him, that was an older mature woman, and it wasn't, like, the barely legal thing anymore," as per Tyla. 

In the conversation, Hefner's ex-girlfriend also drew a comparison between controlling the lipstick shade and life in the Playboy Mansion to a cult. "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," she shared. Previously, Madison also spoke openly about how living in the house impacted her mental health, going as far as to say that the lifestyle there caused her to contemplate suicide, as per People.

Bridget Marquardt was another ex-girlfriend of Hefner's. She backed Madison's statements, saying Hefner would be upset if Madison wore red lipstick and would let other women wear it. Many ladies who lived in the Playboy Mansion have spoken up about the pressure they lived under and how controlling Hefner was.

Marquardt, in particular, confessed she was 'not ready at that moment' when it came to sleeping with Hefner for the first time, though she did not rule it out for a future date. "I was thinking I could get out of this a little while. The first night I was like, 'I'm not ready yet, I'm not going to do anything I don't want to do,'" she said, as per Newsweek. Furthermore, she stated that there were three more playmates who 'put pressure on you' and that she was told she would 'never be invited back' if she did not join the others in Hefner's room.

Hefner died in 2017 at the age of 91. A documentary called Secrets of Playboy came out in 2022 and it featured women talking about life in the mansion. "Every shade of gray happened at the mansion and happened over a span of 40 years,” the director of the documentary, Alexandra Dean, told Variety at the time.

SUICIDE:  If you are having thoughts about taking your own life, or know of anyone who is, please contact The National Suicide Prevention Lifeline at 1-800-SUICIDE (784-2433).
SEXUAL ASSAULT: If you are being subjected to sexual assault, or know of anyone who is, please call the National Sexual Assault Hotline at 800.656.HOPE (4673).