Princess Diana had no problem going against the royal family's outdated and sexist traditions after she married Prince Charles, paving the way for Kate Middleton and Meghan Markle. Her strong and rebellious nature was a large part of what made her so well-liked and what ultimately led to her becoming the icon she is today.
With a legacy of compassion, intellect, and class, she was truly one-of-a-kind. Often celebrated for her defiance, here's a look at the most notable times Princess Diana was caught being a rebel on camera:
Forgoing A One-Of-A-Kind Engagement Ring
Princess Diana shows off her iconic engagement ring. | Facebook
Prior to Princess Diana's engagement to Prince Charles in early 1981, all of the women in the royal family had their rings custom made. Instead of getting a one-of-a-kind engagement ring, however, Princess Diana opted for something she found in a jewelry catalog.
The future princess selected a white gold band decorated by a 12-carat oval Ceylon sapphire stone and 14 solitaire diamonds. Designed by Garrard jewelers, the ring caused quite a stir among the royals. Despite the fact that the ring was inspired by a broach Prince Albert wore in 1840, and later gave to Queen Victoria to wear as her something blue on her wedding day, the royals found it to be too accessible to the public.
Falling Asleep At A Royal Engagement
Princess Diana dozing off at a royal engagement in 1981. | Facebook
Not long after her big wedding, Princess Diana was caught snoozing at the Splendours of the Gonzagas Exhibition Gala. Labeled "Sleeping Beauty," this photo was quickly splashed all over tabloids, many of which criticized her actions.
Little did the public know, the 20-year-old Princess of Wales was pregnant with Prince William, who she later gave birth to on June 21, 1982. To save face, the royal family quickly announced that Princess Diana was with child to excuse her exhaustion.
Giving Birth In A Hospital
Princess Diana and Prince Charles leaving the hospital with their firstborn in June of 1982. | Facebook
Believe it or not, prior to Prince William's birth in 1982, all of the children born into the royal family had been born in a palace. Dating back to the 1840s, a prehistoric method referred to as "twilight sleep" was used during childbirth, which medicated the woman to near unconsciousness. While it ensured a pain-free experience, it also stole any memory of the experience from the new mothers.
For this reason, and probably several more, Princess Diana chose to give birth naturally in a hospital. Both Prince William and Prince Harry were born at St. Mary’s Hospital in London, paving the way for other women in the royal family to do the same.
Relishing In The Spotlight
Princess Diana surprises her husband with a dance in December of 1985. | Facebook
In honor of Prince Charles' 35th birthday, Princess Diana surprised her husband by getting on stage while attending a performance at The Royal Opera House in London. She had secretly practiced a routine with British professional dancer Wayne Sleep to Billy Joel's "Uptown Girl" which combined jazz, ballet, and kickline. While there is no video of the event, a recent episode of The Crown reenacted the dance.
Sleep recalls whispering to Princess Diana at the end of their performance, "You have to bow to the royal box," where Prince Charles sat. Allegedly she responded by saying, "I’m not bowing to him. He’s my hubby," which demonstrates her rebellious nature at the time. Unfortunately, Prince Charles wasn't impressed by her performance. He saw it as an embarrassment to the royal family a "lapse in royal etiquette" according to The Diana Chronicles.
Experimenting With Fashion
Princess Diana at a royal event sponsored by the White City Greyhound Charity at Wembley Stadium in April of 1988. | Facebook
Despite both written and unwritten royal family fashion rules, Princess Diana would rarely comply. One of the most obvious customs she broke was attending royal events in suits, which were only to be worn by men. She would also wear tight, revealing cocktail dresses that are a big no-no according to the Queen.
Princess Diana leaving St. Mary's Hospital in London after her newborn nephew on March 15, 1994. | Facebook
While women in the royal family often wore gloves and hats, Princess Diana refused. Her nail polish and makeup were also rarely understated as required. Considering how young she was, it should hardly be surprising that she enjoyed experimenting with her style!
Partaking In Non-Royal Events
Princess Diana running barefoot at Richmond Rugby Club for Prince William's annual school event in June of 1989. | Facebook
Within the royal family, the children were traditionally homeschooled, however, Princess Diana wanted her boys to get a taste of life outside of the palace. She would often allow them to eat fast food, ride with them using public transportation, and take them to theme parks where they stood in line just like everyone else. Princess Diana was a mother first and a member of the royal family second.
Princess Diana on a waterslide at Thorpe Park with Prince Harry in April of 1992. | Facebook
This meant she never missed one of her son's school events, including the notorious annual barefoot race shown here:
Princess Diana running barefoot in a school race during Prince Harry’s sports day in 1991.
Having An Affair
Princess Diana presenting the Captains' and Subalterns' Cup to James Hewitt after a Polo Match in August of 1989. | Facebook
It was well-known among the royal family that Prince Charles was cheating on Princess Diana with Camilla Parker Bowles. However, they expected her to sit idly by while her husband walked all over her. Instead, Princess Diana did what any strong woman would do in this situation. She had an affair of her own.
Princess Diana fell for her horseback riding instructor, Major James Hewitt. While she admitted that she “adored” him and was “in love with him,” he betrayed her in a major way. Hewitt used his relationship with her to make money, selling their story for a tell-all book and trying to sell her letters to him for £10 million. It may not have ended well, but Princess Diana was able to fill the void caused by her husband's neglect.
Wearing The Revenge Dress
Princess Diana at a Vanity Fair party just after Prince Charles publicly admitted he was having an affair in June of 1994. | Facebook
Despite the world knowing that Prince Charles and Princess Diana had separated, no one knew why. In a desperate attempt to win over the public, the prince came clean in a documentary and admitted he was not only having an affair with Camilla Parker Bowles but was in love with her.
Rather than sit at home wallowing, Princess Diana got revenge in the best way possible. She went to a Variety Fair party in a dress that still has people talking decades later. It was clear she wasn't going to let the deterioration of her marriage force her into hiding, even though that's what the royal family would have preferred.

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