When Princess Diana Dressed Up 'Like a Man' to Enter a Gay Bar With These Iconic Celebrities

Princess Diana was one of the most beloved members of the Royal Family to date. Her dignified grace and humility made admirers fawn over her. Although she was briefly married to King Charles and welcomed two children, Prince William, and Prince Harry, the way she navigated divorce and co-parenting earned her even more fame than before.

The late Princess was known to be an iconic woman in the years she was alive. One of her most noteworthy moments was when she dressed up as a man to allegedly enter a gay bar with Freddie Mercury and Kenny Everett in the 1980s.

Princess Diana cherished the privacy she had despite being famous and preferred being unrecognizable by paparazzi. According to a 2013 article by The Daily Mail UK, just so she could have a fun night out with her friends, Queen frontman Mercury, Everett, and Cleo Rocos, Princess Diana donned the attire of a man! The late member of royalty was a big fangirl of Rocos and didn’t want to pass up on the opportunity to hang out with the star.

 In her book, “The Power of Positive Drinking” Rocos recalled the time all four of them went out for a scandalous night out at the ‘Vauxhall Tavern.’ The late princess had never heard of such a place and eagerly wanted to visit. Despite many efforts to dissuade her, the late princess was in ‘mischief mode.’ Rocos recalled, “She turned to Mercury who declared: ‘Go on, let the girl have some fun. Can you imagine?” 

Rocos continued to note that Princess Diana “wanted the thrill of going in undetected to order one drink and would leave right, away.” The author mentioned that if she was let in on this one little deed, she’d ‘promised’ to leave without question. So, the foursome went on with the plan to disguise her.

Because, well, she can’t just walk into such a place with the title she had. Rocos described the scene saying, “She tried on the outfit Kenny had intended to wear: a camouflage army jacket, hair tucked up into a leather cap and dark aviator sunglasses.” Apart from her carefully curated ensemble, Princess Diana’s short hair was a major advantage that complimented the rest of her outfit. 

After the transformation was complete, Rocos and the rest of the gang “scrutinized her in the half-light” and decided that she “might just - just pass for a rather eccentrically dressed gay model.” Now that that crew was all dressed up, it was time for the party! It’s safe to assume that it was a big success as Rocos claimed in the book. The late princess took in the peppy and unique atmosphere and ordered herself a neat glass of white wine followed by a beer. As promised, she finished her drink and left without a single person taking notice of a literal member of royalty amidst them.

Editor's note: This article was originally published on February 14, 2024. It has since been updated.