Although there were certainly sides to Princess Diana that were quiet, shy, and reserved, she also had a bit of a wild side in her day. Her innate rebelliousness would likely have constantly gotten her in trouble with the royal family, as Diana frequently broke protocol during her time as a royal. But even though she may have been a headache for everyone in the palace, from Queen Elizabeth to the guards, she's a bit of an inspiration to us.
Diana did her best to lead a normal life despite her complicated situation and status. She never lost her sense of realness, and she wasn't afraid to stand up to a challenge — even when that challenge was the archaic rules the royal family dictated.
Here are 15 of Diana's wildest moments in the public eye.
Changing Her Vows
A rebel from the start, Diana became the first royal woman to omit the line about obeying her husband from her wedding vows. Since then, both Kate Middleton and Meghan Markle have followed in their late mother-in-law's footsteps and skipped the line too. But could they have been so brave without Di setting the path?
Check out our Meghan Markle page for all the latest news about Meghan, Prince Harry, and their growing family.
Bringing Prince William to Australia
In the past, royal children usually stayed home while their parents carried out official business, but Diana changed the game when she brought baby Prince William along on her Australia tour. We can't believe anyone would have expected Diana to leave her little one behind, but at least she was able to insist that he come with her in the end.
Partying With Freddie Mercury
Seeking an evening free from photographers and responsibilities, Diana reportedly once dressed up in drag with Queen frontman Freddie Mercury to go to a gay bar. There's so much about this story that's just wild, from Diana being friends with Freddie in the first place to picturing her dressed up like a guy to avoid the paparazzi.
Donning Menswear
The princess didn't just dress up like a guy once for a laugh with Freddie Mercury — Diana was a patron of menswear for her whole life. She was always pushing the fashion envelope, including by wearing more traditionally masculine clothing, like suits. It was bold for any celeb to style themselves this way at the time, much less a royal.
Playing Pranks
During Sarah Ferguson's bachelorette party, Diana and Sarah decided to play a prank where they dressed up as policewomen to try to sneak into Prince Andrew's bachelor party. The prank included a mock arrest and everything. We can totally picture these two rebel royals getting into this kind of trouble.
Diana Even Pranked William
Diana's practical jokes weren't limited to strangers. She once pranked her own son — on his birthday, no less. William recently recalled that for his 13th birthday, Diana invited a bunch of her supermodel friends to his party. "I didn't quite know what to say and sort of fumbled. I think I pretty much fell down the stairs on the way up. I was completely and utterly sort of awestruck," William said.
Dancing to 'Uptown Girl'
Diana attempted to surprise husband Charles with a dance while the couple was out at the Royal Opera House. She slipped away from her box seat and went on stage in a slinky white gown to perform a routine to Billy Joel's "Uptown Girl." Charles reportedly hated the attention Diana got from the performance, but we just can't even believe this is a real story. Diana was wild.
Sneaking Her Sons Out of the Palace
The palace gates and guards are there to protect the royals, but Diana was not above giving these safety precautions the slip from time to time. She particularly loved to sneak William and Harry out with her and take them to McDonald's for a bit of real childhood in the form of fast food. That has to be one of their favorite memories with her.
Sneaking Her Boyfriends In
What can go out can also come in, right? Diana had a few love affairs while living in Kensington Palace — both during and after her divorce. And many of the times she met up with her lovers, it was after they'd been snuck into the palace in the trunk of her butler's car, or something. So much for the palace protection staff.
Wearing Shorts — And Tight Ones, Too
It's so rare for the royals to wear shorts that Kate Middleton stirred up a media firestorm when she did it for the first time in 2019. But people are apparently forgetting the royal rebel who came before — Diana. She broke protocol by visiting a public gym and donning skimpy bike shorts to most of her workouts. Did Diana invent athleisure? Basically.
And Showing Cleavage
This happened more after Diana and Charles separated and the princess was free to wear what she wanted, but working royal or not, it was still a bold act for Diana to show off her cleavage in these low-cut dresses. The royals are typically all about modesty and professionalism, but Diana was just there to have fun and look great.
Confronting Camilla
Although Diana could be shy, she was also fearless in many ways. One time she even confronted her husband's lover, Camilla Parker Bowles, at a party. Diana knew Camilla and Charles were having an affair, and she wasn't afraid to let Camilla know that. "I do know what is going on," she reportedly said to Camilla. "Don't treat me like an idiot."
You go, girl.
Wearing the Revenge Dress
Diana would frequently tell stories with her fashion, like when she wore this daring little black dress. She donned it the same night Charles went public with the news of his affair, and Diana was then pictured looking so amazing anyone would have questioned what Charles had been thinking. It was truly an iconic outfit from the princess.
Helping a Mourning Friend
Diana once helped a grieving friend bury her stillborn baby in the gardens at Kensington Palace. Had the royal family known what was going on, perhaps they would have nixed the idea. But we think it's so kind and sweet that Diana undertook such a task to help her friend. She was a rebel in the absolute best way.
Honest About Her Struggles
The unofficial royal motto is "never complain, never explain," but Di didn't live by those same rules. In her stunning Panorama interview, Diana opened up to explain and complain about a number of traditionally taboo topics, including her self-harm and disordered eating. It can't have been easy for her to talk about those things, but she wasn't afraid to do it.
