Hugh Hefner, the founder of Playboy, famously detested when his playmates wore red lipstick.. A rule that his ex-girlfriend Holly Madison revealed in various interviews. This preference wasn’t immediately apparent when Madison first joined the Playboy Mansion in 2001, but it became a point of contention once she moved into Hefner’s bedroom and assumed the role of his main girlfriend. Initially, he didn’t mind her wearing lipstick, but his attitude changed over time. Which she attributed to deeper issues of control and image perception.
Red Lipstick and Age Perception
Madison alleged that Hefner’s disdain for red lipstick was rooted in his desire to maintain a “fresh-faced” look for his playmates. Believing that makeup, particularly bold colors like red, made them appear older. According to Madison, Hugh Hefner associated red lipstick with an era of women in the 1950s who were “somebody’s older sister” and more mature contrasting with his vision of youthfulness and sensuality. He wanted his playmates to look young and innocent, which he believed the absence of makeup could achieve. Hefner’s ideals for women in the Playboy Mansion were defined by a preference for a barely-there aesthetic. Something that would emphasize youthfulness and minimize the appearance of maturity.
A Controlling Environment
Madison described Hefner’s stance on red lipstick as more than just a personal preference—it was a method of control. She believed that Hefner’s rules, including the strict no-red-lipstick policy, contributed to a cult-like atmosphere in the mansion. According to her, Hefner would often gaslight his girlfriends into believing that his actions were for their own good. While subtly reinforcing his control over their appearances.
Scrutiny and Fear
This is a sentiment that Madison, alongside other former playmates, has shared on multiple platforms. Including the 2021 A&E docuseries Secrets of Playboy. Bridget Marquardt, another former girlfriend, corroborated Madison’s claims. Explaining that Hugh Hefner would become enraged if Madison wore red lipstick, though he allowed other women to do so without as much scrutiny.
Lipstick as a Symbol of Control
To Madison, Hefner’s dislike for red lipstick wasn’t just a quirky preference; it became a powerful symbol of his ability to control how his playmates presented themselves. The pressure to conform to his ideal image created a toxic environment within the mansion. Madison compared her experience living in the mansion to being part of a cult, where new arrivals were treated kindly while longtime residents were subjected to increasingly restrictive rules. The higher Madison rose in the Playboy hierarchy, the more controlling Hefner became regarding her choices, including the color of her lipstick. This, she explained, was part of a broader dynamic where Hefner aimed to mold and control the women who lived under his roof. Reinforcing a culture where youth and compliance were prioritized above all else.
A Legacy of Control and Criticism
Hugh Hefner’s obsession with maintaining a youthful image for his playmates speaks volumes about the power dynamics in the Playboy Mansion. While many women, including Madison, have since left the mansion and spoken out about their experiences, the legacy of Hefner’s control over his girlfriends’ appearances has raised important questions about the deeper psychological toll that such expectations can have. For Madison, the no-red-lipstick rule stands as one of the many ways Hefner exerted dominance. Creating an unsettling dynamic in a place that was publicly portrayed as a paradise of freedom and glamour. Madison’s reflections on this chapter of her life continue to reveal the disturbing undercurrents beneath the Playboy Mansion’s glossy surface.