With August 31 marking the 25th anniversary of her untimely death, we are resharing one of our favorite anecdotes about the beloved former princess. This story not only illustrates what a great ally Diana was — it also gives us a peak into the lesser known humorous and fun-loving side of her personality.
In the late 1980s, at the height of fear and stigma around HIV, Diana regularly visited AIDS wards in hospitals. She was famously photographed shaking hands with a man who was in the advanced stages of HIV, which shocked many at the time — but also helped start a global conversation about the need to learn the facts about the virus.
Diana was also a lifelong ally and supporter of the LGBTQ+ community, and one particularly amusing story illustrates this beautifully, and shows that beyond the princess, the advocate, and the celebrity… was a human being. And a pretty fun one at that.
The anecdote comes from a book called The Power of Positive Drinking, written by comedian Cleo Rocos. According to Rocos, in the late ‘80s, she, along with singing legend Freddie Mercury and television actor Kenny Everett, snuck Princess Di into a gay bar — and dressed her in boy drag.
In efforts to disguise her so that she could sneak into the Royal Vauxhall Tavern in south London, the group dressed Diana up as a “male model.” Rocos goes on to describe how they dressed the princess in “an army jacket, black cap, and sunglasses,” and Diana enjoyed a night out on the town, free of any unwanted attention.
“When we walked in ... we felt she was obviously Princess Diana and would be discovered at any minute. But people just seemed to blank her. She sort of disappeared,” said Rocos. “But she loved it.” The presence of Mercury and Everett helped take the attention off Diana, though she did make a cute dude, joked Rocos.
“She did look like a beautiful young man,” explained Rocos. “She was always a very fit girl, so they might have thought, ‘There’s a nice young man with pert buttocks.’”
It should be noted that Diana's sons, particularly Prince Harry, continue to carry on her work around issues like homelessness and HIV.