14 Times Princess Diana Broke Strict Royal Rules

Princess Diana wasn't afraid to break the royal rules. So whether you're a genuine fan of the British royal family or just an avid watcher of The Crown, you know full well that the royal family has strict rules that must be followed at all times. The very enforced guidelines touch all aspects of life — from clothing and jewelry to child-raising to wedding details, the royal influence is real.

But if you were to ask anyone on the street about one royal family member that defied the odds, chances are they'd say Princess Diana. From her early days of "Shy Di" to her beloved days as the "People's Princess," Diana went against the grain and carved a space for herself both within and outside of the royal family. By interacting with people with such genuine interest, advocating for marginalized groups, and devoting herself to her kids, Diana made a name for herself that was defiant, bold, and authentic.

But royal protocols followed Diana wherever she went, and as such, we've been able to track down just a fraction of the times she broke tradition. So buckle in, because here are 14 times that Princess Diana broke strict royal rules.

One of the most recognizable engagement rings in history has to be Princess Diana's. The sapphire ring surrounded by diamonds is stunning, and made its way to Diana's finger when she got engaged to Prince Charles. But what many don't know is that the engagement ring broke protocol. As noted by Brides, the $60,000 ring was provided to Diana as an option by crown jeweler Garrard — but what made her choice so controversial was that the ring was also featured in the jeweler's catalog. 

So it was in a magazine, what's the big deal? Well, as noted by Vogue, members of the royal family were not pleased with Diana's choice, given that a commoner could purchase the same ring. By their standards, the ring "wasn't considered unique and also wasn't bespoke." Perhaps this was the first step Diana took in becoming the "People's Princess," because not only did she choose such a gorgeous ring, she selected a piece of jewelry that was accessible to everyone. So even before she married into the royal family, she was already breaking the strict rules.

According to Marie Claire, Queen Elizabeth interacted with her children in a very poised way; every interaction seems formal and distant. "There's an instant barrier between them," body language expert Patti Wood said. But Princess Diana broke royal protocol as a mom, and showed her love and affection to her sons, Prince William and Prince Harry. "Of all the images that have burned into the public memory, few are more incandescent than one from Toronto [in 1991]," Katrine Ames wrote in Newsweek in 1997. "As Harry and William approach, their mother rushes to meet them, her body canted forward, her arms flung wide, with a smile that would light the darkest heart." 

Not only did Diana break the strict rules concerning how royals interact with their kids, but she took her sons on outings that defied the expectations; she took the boys out for burgers and let them wear jeans. Diana also took them white-water rafting and let them ride their bikes. To put it simply, Diana gave her boys the most normal life she could, hoping that it would give them a healthy upbringing and solid foundation.

It seems like everything changes when kids get involved, and that was the case for Princess Diana. When she gave birth to her first son, Prince William, she broke royal protocol and chose to have her baby in the hospital, not at home. This might not seem like a big deal now, but at the time, the choice not only broke strict royal rules, but breathed new life into the changing traditions of childbirth. 

William was the first heir to the throne born in the hospital, breaking generations of tradition. "George VI was born at Sandringham Estate in 1895, Queen Elizabeth II was born at her grandparents' home in 1926, and Prince Charles was born in Buckingham Palace in 1948," Reader's Digest reported. So when it came time to give birth to the future King of England, Diana knew that her choice to go to the Lindo Wing of St. Mary's Hospital would break all kinds of protocol. 

With her choice, Diana ushered in a new royal protocol, one that her son William has followed with the births of his own children.

There are moments in a person's public life where they challenge expectations so outlandishly that everyone pays attention. That moment came for Princess Diana in 1981, when she attended her first public engagement with Prince Charles — and broke strict royal rules. As noted by The Times, Diana chose to wear a black taffeta gown with a slightly revealing neckline; the dress sparked outrage because of its silhouette as well as its color. 

Up until that point, wearing black as a member of the royal family was strictly reserved for funerals. "Generally it is thought that black is not usually worn unless in mourning, although Diana Princess of Wales did occasionally wear it for evening functions," Alexandra Messervy, The English Manner Chief Executive, said to InStyle. 

The moment Diana stepped out in black for the first time was such a big deal that the taffeta dress in question has stood as a testament to her bold behavior. People clearly caught on to the importance of the dress, because it sold at auction for over $250,000.

Princess Diana was born into British nobility, but she was a working woman in her early days. According to Good Housekeeping, Diana was a part-time kindergarten teacher in London before getting engaged, and as such was the first wife of a royal family member to have a paying job. A young woman having a job like the future royal did in the '80s doesn't seem like that big of a deal now, but at the time, Diana's contribution to the workforce broke strict royal rules — though we think it makes her more relatable.

The fact that Diana worked was brought up again by UPI when she and her husband announced her first pregnancy. "Princess Diana, the former kindergarten teacher who married Prince Charles in a glittering ceremony in July, is expecting a baby this June," the 1981 report read. "The palace said Diana, 20, who worked as a kindergarten teacher before her wedding, is in good health." The focus her employment got is a little weird in retrospect — we can't see our part-time gig as a Starbucks barista making the papers any time soon!

The royal family dress code is pretty brutal, and Princess Diana broke many of those strict rules while married to Prince Charles. But one of the biggest protocols she breached didn't have anything to do with the dresses she wore, or even Diana's blue eyeliner that was her staple makeup look; it had to do with her fingernails. As noted by Woman's World, the royal family had (and still has) strict rules when it comes to nail polish. "No bright, flashy nail colors" is the rule in question, leaving the royal women with limited options — think light pink, nude, or clear polish only.

So what did Diana do with that rule? She completely ignored it, and was seen on occasion with bright red nails. It's such a small thing to pay so much attention to, really, but it was a rule that Diana thought was worth breaking. "I don't go by a rule book," she said during a famous sit-down interview with the BBC. "I lead from the heart, not the head, and albeit that's got me into trouble in my work, I understand that."

The royal family has been known to have strict rules regarding the press, and to never let scandals get into the headlines — just think about the first season of The Crown. But Princess Diana didn't conform to expectations, and had a relationship with the press that was unlike the other royals. 

As noted by the BBC, Diana's dynamic with the media was full of pros and cons; on one hand, she would complain about the lack of privacy. But on the other, she would use the press to her advantage and seek out the attention she craved from the public. "In the run-up to her divorce from Prince Charles and in the years afterwards she sometimes fed information to journalists," the BBC reported, adding that she'd approached journalists on her own time and with her own agenda. 

Diana put her experience with the press in her own words: "I seemed to be on the front of a newspaper every single day, which is an isolating experience, and the higher the media put you... the bigger the drop. And I was very aware of that."

One rule that women of the royal family have traditionally followed is wearing gloves. For formal occasions, while meeting supporters, and for everything in between, it seems like gloves are the go-to option (especially for the Queen). But as noted by People, Princess Diana broke that strict rule for a heartwarming reason. "She abandoned the royal protocol of wearing gloves because she liked to hold hands when visiting people or shake hands and have direct contact," explained Eleri Lynn, curator of Diana's clothing exhibit at Kensington Palace. "She also stopped wearing hats because she said, 'You can't cuddle a child in a hat.'" 

Lynn explained that after Diana's divorce, she made a point of simplifying her look in order to focus on the work at hand. She made a name for herself by caring for the people who adored her — visiting children's hospitals and greeting people who'd waited to see her — really becoming the "People's Princess." "You see through the course of the display the princess really getting a sense of her own style," Lynn said. "[Becoming] this fantastically glamorous, self-confident stylish woman."

This royal protocol made our blood boil, even when we watched it play out in The Crown, so prepare yourselves. According to The New York Times, at the time of her wedding, Princess Diana made the choice to break with strict royal rules and change the wording of her vows to Prince Charles — and rightly so. The royal women before her — Queen Elizabeth, Princess Margaret, Princess Anne, and many others — all vowed during their weddings to "obey" their husbands. Yes, you read that correctly. 

The vow to obey came from the Anglican Book of Common Prayer that dated back to 1662, and Diana clearly thought that enough was enough. When she got married to Prince Charles at St. Paul's Cathedral in that iconic, puffy wedding dress, Diana vowed to "love him, comfort him, honor and keep him, in sickness and in health," and thankfully, obeying him was not included.

It was a break from royal precedent that we believe was long overdue, and in hindsight, the confidence and conviction Spencer had to break such a strict royal rule is admiral.

It was the interview watched around the world. In an expository sit down with the BBC, Princess Diana spoke about her mental health, and by doing so, broke the strict royal rules of facade and perfection. She spoke in detail about many issues, from infidelity to her postpartum depression, and the toll it took on her self worth. "Maybe I was the first person ever to be in this family who ever had a depression or was ever openly tearful," she revealed, calling out the royal family for its lack of support. "And obviously that was daunting, because if you've never seen it before how do you support it?" 

In a departure from pretending that everything in her life was fine, Diana addressed her struggle with bulimia and how it chipped away at her self-esteem. "It was a symptom of what was going on in my marriage," she revealed. "I was crying out for help, but giving the wrong signals, and people were using my bulimia as a coat on a hanger: they decided that was the problem — Diana was unstable." Talk about breaking down your walls.

Life in any institution, like the royal family or even the First Family of the United States, seems to be private and isolating. That was clearly a sentiment that Princess Diana caught onto quickly, because by the time she was living life as a royal, she broke strict royal rules in order to escape the palace. 

As noted by E! News, Diana would get in and out of the grounds by wearing wigs and disguises. Sometimes, she would even hide in a car and get out that way — sounds like being a prisoner in your own home if you ask us.

Diana's escape attempts clearly influenced her sons, because both Prince William and Prince Harry used motorbikes to sneak out on occasion. The issue of privacy again garnered attention again when Meghan Markle used plays out of Diana's book to escape. "Meghan's been using different disguises, hats," an insider explained. "They're being extremely clever so they can go in and out without being seen. They are taking a completely different approach than William and Kate."

Princess Diana seemed to work tirelessly to give her two sons, Prince William and Prince Harry, as much of a normal life as possible; by doing so, she broke strict royal rules when it came to their schooling. According to PopSugar, the children of the royal family had been educated by a governess or tutor on the palace grounds (even Queen Elizabeth doesn't have a formal education). But that was a tradition that Diana clearly didn't take a liking to, because when William was 3 years old, she enrolled him in public school, becoming the first heir to the British throne to do so. 

William clearly liked the experience as a child, because he and his wife, Kate Middleton, followed the new precedent set by Diana for their own children; Prince George attended the Westacre Montessori School, and Princess Charlotte also attended nursery school. Additionally, after their days in the public school system, both William and Harry attended Eton College — an all-boys private school known for its notable alumni — Boris Johnson, David Cameron, and Eddy Redmayne, just to name a few, via Insider.

If Princess Diana was known for anything, it was the way in which she met with people. She was often seen cuddling kids and interacting with people who had waited to speak to her. And, as noted by Good Housekeeping, Diana had a distinct style of engaging with people that broke strict royal rules — she crouched down to people's level, even down to the ground with children, in order to connect with them fully. "Diana was the first member of the royal family to do this," Ingrid Seward, editor of Majesty magazine, said. "The royal family used to say that everyone had to be deferential to them. But Diana said, 'If someone might be nervous of you or you're speaking to a very young child or a sick person, get yourself on their level.'" 

Clearly Diana was comfortable doing so, because she was often seen embracing individuals in all kinds of circumstances. It could be one of the reasons why her death was that much more devastating for the everyday people who loved her — they felt so connected to who she was.

We love a mom who will throw caution to the wind, and Princess Diana did just that while participating in the annual Sports Day race at her sons' school. In 1991, Diana attended the event and took part in the parents' race; the video of the race, resurfaced on the internet, shows a barefoot Diana giving everything she's got. 

Diana's participation in the race completely broke strict royal rules, as noted by The International News, but in the video, she looks so happy that we really hope royal protocol was the last thing on her mind. "While she did not snag away the winning title, she was lauded widely for putting in so much effort to make her boys happy," the newspaper reported. Clearly, Diana's approach to parenting was consistent; she gave the boys everything she had and more.

All in all, royal protocol couldn't keep Princess Diana down, and we're grateful that it didn't.