20 Times Princess Anne Proved That She's A Total Boss

Princess Anne is arguably the most relatable member of the royal family. Not only is she not afraid to break some royal rules occasionally (read: often), but she's also not your typical princess. In fact, it might be safe to compare Anne to her late aunt, Princess Margaret. Like Margaret, Anne is a bit of a royal rebel, and she definitely doesn't embody the classic royal stereotype of a timid princess.

Princess Anne inherited Queen Elizabeth II's stoicism and dry wit, but beneath her cool demeanor, there's a warmth only those closest to her get to see. "She's a gem. Truly one of the nicest and most hardworking of them all," a years-long Buckingham Palace employee told Vanity Fair. Being a royal is not the only thing Anne is good at — she's also an accomplished equestrian and will likely ace an advanced driving test (more on that later). From sneaking out of the palace to racking up a criminal record, blending in with the masses on public transport, and telling an armed criminal to bugger off, it might be safe to say that Princess Anne is the most audacious (and perhaps one of the bravest) royals around.

Anne might once have been King Charles III's spare, but she's shown herself to be invaluable to the monarchy, especially amid the king's recent cancer diagnosis. Join us as we take a look at the princess royal's most memorable and bold shenanigans over the years, and get ready for some good laughs.

While boarding school is many kids' worst nightmare, Princess Anne couldn't wait to leave the palace halls to do just that. The only problem was that it was tradition for female members of the royal family to attend school at home. Even Queen Elizabeth II, for all her accomplishments, never attended boarding school. Princess Anne followed in her mother's footsteps at first, receiving her education within the walls of Buckingham Palace with Catherine Peebles, her governess. But, the moment she was old enough to be admitted to boarding school, Anne jumped at the chance.
Even though her brother, King Charles III, had a less-than-great experience at boarding school, Anne remained undeterred. "I was ready to go to school. I had a governess and two friends, and that was never going to be enough, really, so I was only too pleased to be sent off somewhere else," the Princess Royal told Vanity Fair in an interview. "I think boarding school has been demonized by some when, in fact, it's a very important aspect to have available, and many children actually thrive in it," she explained. Anne attended Benenden School in Kent from 1963 until 1968, obtaining two A-levels and six O-levels.

Becoming the first female royal to attend boarding school was only the first of many accomplishments for Princess Anne.
The Princess Royal has a great love for horse riding, and she became an accomplished equestrian in her youth — so accomplished, in fact, that she ended up competing at the Olympics in Montreal in 1976 with Queen Elizabeth II's horse, Goodwill. While she didn't win a medal, she boasts three European Championship medals.
Speaking to Vanity Fair, Anne admitted that if she hadn't been bound by royal duties, she would probably have pursued an equestrian career. "I thought if I was going to do anything outside of the royal family, horses was likely to be the best way of doing it," she said. "But then you have to find the right horse at the right time. The original horse I rode was bred as a polo pony and should never have been an event horse, but it worked, so that was very satisfying. But I always knew it was going to be limited time."
However, Anne made the most of her time in the Olympic spotlight, and in 1988, the International Olympic Committee appointed her as one of its members. As Director of the London Organising Committee of the Olympic and Paralympic Games, Anne also had a hand in ensuring that London won its bid to host the Olympic Games in 2012.

Princess Anne likes fast cars. She loves them so much, in fact, that she once snuck out of the palace to race one. In 1971, Anne and Formula 1 champion Sir Jackie Stewart took a road trip to race a sportscar in Silverstone without Queen Elizabeth II knowing a thing. While Anne and Stewart were chatting via video call for the latter's dementia charity, the two spoke candidly about the day. Stewart recalled that Anne wasn't exactly happy that he was the one driving them to Silverstone when he picked her up at Windsor.

The car the two were driving in was, in Stewart's words, "a very hot British touring championship car." No wonder Anne was itching to take the wheel. Stewart said that he always knew Anne to prefer the driver's seat. "You drive more than any other lady I know. You were always keen to be behind the wheel, that was for sure," he said. Anne later admitted that she's not "the world's best passenger."

Once the two arrived at the track, Stewart allowed Anne to have some fun, and it turned out that the royal didn't even need much coaching — she was pretty much a natural, and Stewart eventually lost count of the laps she took around the track. A picture taken on the day was kept out of the press at the time because Buckingham Palace didn't have any knowledge of Anne's little outing.

While chatting with Formula 1 champion Sir Jackie Stewart for his Race Against Dementia charity, Princess Anne revealed she is quite adept at mucking out horse stalls.
Stewart recalled Anne being a tad late to an event once, and when he asked her what the hold-up was, she told him that she'd been cleaning stables. "And I thought, for God's sake, the princess was cleaning out stables? I don't really think that was appropriate," Stewart said. Anne merely grinned, explaining that her mother, Queen Elizabeth II, taught them from a young age that owning a horse meant you had to take care of it, too. "We were brought up that way," Anne said, "If you had ponies and horses, if you rode, you had to understand about them and what they needed. The first thing you did and the last thing you did was to look after them." She added that her mother was very strict regarding this — she wasn't allowed to simply ride her horses and then leave them to be taken care of afterward by palace staff — it was her responsibility to do all the dirty work as well.

It might be safe to say that criminals still take a wide berth around Princess Anne, thanks to her cool demeanor and sharp tongue that took over the last time someone tried to mess with her.

The incident in question took place in 1974. Anne was traveling to Buckingham Palace after attending an event when a man named Ian Ball fired shots at her vehicle, injuring the driver. A nearby journalist and two police officers also suffered gunshot wounds. Anne, however, remained perfectly calm. Ball approached her and told her that he was going to kidnap her and demand a £2 million ransom, which he said would be donated to the NHS. Anne wasn't impressed or intimidated. When Ball told her to get out of the car, she reportedly shot back, "Not bloody likely!"

"He said I had to go with him ... I can't remember why. I said I didn't think I wanted to go. I was scrupulously polite because I thought [it was] silly to be too rude at that stage," she recalled during an interview on "Parkinson in Australia," adding that she asked him to be on his way so they could forget about the whole ordeal (via Woman & Home). Anne told Vanity Fair that the only time she got upset was when her dress got torn during the incident, which, in her words, "[made me] lose my rag." Police managed to dissolve the situation, and Anne went home without a scratch — and with a killer reputation.

There's a reason Princess Anne likes driving sports cars — she likes to speed. In October 1990, reports surfaced that Anne had been fined $295 after exceeding the speed limit twice. Anne was driving 77 mph in a 60 mph zone the first time she was caught. The second time, she was driving 90 mph in the same speed zone. Oops. When asked for comment, Buckingham Palace followed its age-old protocol of replying with "no comment." Because of these two offenses, Anne's driver's license was revoked for a month. Ever the rebel, this didn't deter the Princess Royal from burning rubber again in 2000 in what was quite a hilarious turn of events.
Anne was making her way to a royal engagement, found herself in slow traffic, noticed a police car behind her, and thought it was there to escort her. She stepped on it to get out from behind the slow-moving cars so she was easily visible to her "escort." When the car started flashing its lights at her, Anne thought it was thanking her for moving into its sights. In the meantime, the cops wanted her to pull off so they could write her up because she was driving 93 mph in a 70 mph zone. A guilty plea in court and $570 later, Anne was free to take to the road again guilt-free, albeit with an extra five penalty points against her license.

Princess Anne and Sir Timothy Laurence's love story is the kind you see in movies: Luarence was Queen Elizabeth II's equerry, a fancy name for an assistant, and he and Anne met within the palace walls and fell madly in love. The only issue was that Anne was already married to Mark Phillips. That relationship didn't last, however. There were whispers that both had engaged in extramarital affairs throughout their marriage, and things quickly escalated when The Sun was sent love letters Laurence wrote to Anne, stolen out of her briefcase. Instead of breaking the story of the year, the tabloid chose to hand the letters over to the police, sparing Anne and Laurence the embarrassment of having their private conversations leaked to the public. Anne's marriage to Phillips ended shortly after.
Prince Philip was reportedly livid that Laurence had gotten involved with his daughter, but Queen Elizabeth was more forgiving. Anne and Laurence got married shortly after her divorce from Phillips was finalized — but it wasn't a simple process. In those times, members of the royal family weren't exactly allowed to remarry in the Church of England if their ex-spouse was still alive. Anne, ever practical, married Laurence in a church in Scotland, which didn't adhere to the same rules. Remarrying after her divorce effectively made Anne the first member of the British royal family to ever do so.

Princess Anne is a living legend in more ways than one. Many think that Princess Diana broke the tradition of giving birth at home, but Princess Anne actually made that history. Most importantly, she's the one who started the tradition of giving birth at St. Mary's Hospital's Lindo Wing and posing on the steps with your newborn. Yup, turns out Diana was just following in Anne's footsteps.
When Anne gave birth to her firstborn, Peter Phillips, in 1977 at the Lindo Wing. She didn't pose with him on the steps, however. She set this tradition when she gave birth to her second child, Zara Phillips (now Tindall), in 1981. Anne wasn't accompanied by her husband, Mark Phillips, as she smiled at photographers, but it was an iconic moment nonetheless. About a year later, Princess Diana and then-Prince Charles posed on the same steps with Prince William after Diana gave birth at the Lindo Wing. The tradition continued when Prince Harry was born, and Prince William and Princess Catherine have since followed suit.

In another break with royal tradition, Princess Anne chose not to give her children royal titles. When rumors were swirling that this was the case, many found it hard to believe and were surprised when the palace confirmed it. In true Buckingham Palace style, the public wasn't told why Anne and her husband had decided to forfeit their children's titles. Still, the speculation was that Anne and Phillips didn't want their children constrained by the monarchy.

It turns out those rumors were mostly accurate. Speaking to Vanity Fair in 2020, Princess Anne finally explained her decision. "I think it was probably easier for them, and I think most people would argue that there are downsides to having titles. So I think that was probably the right thing to do," she said.

When you ask Anne's children what they think, it's clear that she did right by them. While appearing on the "Seven: Rob Burrow" podcast, Anne's daughter, Zara Tindall, praised her mother for the decision. "From my point of view, I was obviously very lucky that my mother didn't give us any titles, so I really commend her on that," she said. "We were very lucky that we kind of got to do it a bit our own way."

Princess Anne might have access to chauffeurs and private helicopters, but she's perfectly happy to take the London Underground occasionally. In 2020, the Princess Royal caused quite a stir when she hopped on the Tube. At first, no one recognized her. It was London Fashion Week, and the Underground was very busy. Anne journeyed to St. Paul's and then traveled to an engagement related to London Fashion Week.

While most people didn't notice the princess (because who expects to see a royal on the Tube?), some of the workers from the Underground recognized her and could hardly believe their eyes. "She came through with another older woman and her security. We weren't expecting any royalty. Hardly anybody seemed to notice them," a Transport for London staff member told the Daily Mail. Given Anne's no-nonsense attitude and proclivity for breaking the rules, it's not altogether surprising that she opted for public transport, but it was odd that she chose the crowded Underground amid the pandemic.

If you've ever wondered who the hardest-working member of the royal family is, wonder no more: it's Princess Anne. Regarding the number of royal engagements each member tallies yearly, the Princess Royal usually comes out on top. "The amount of time she dedicates is remarkable. There's a lot that goes on that isn't in the public eye," chairman of the Carers Trust, John McLean, told Vanity Fair.
In 2019 alone, Princess Anne attended over 500 royal engagements, beating her brother, King Charles III. She bested him again in 2023 with a total of 457 engagements. She clearly likes to stay busy — twiddling thumbs and spending her free time drinking tea simply isn't how the Princess Royal rolls. You'll find her attending up to five engagements daily, to the distress of some of her aides. "I make their lives more difficult in terms of the logistics, I'm afraid, but if I'm going to be in London, I don't want to be hanging about. A lot of stuff goes on here, so there's a question of filling in the time," Anne told Vanity Fair.
As for retirement plans, Anne seems happy to continue her royal duties as long as she is able, although she admits that her mother and father both worked for far longer than she initially planned for herself.

We're all curious about whether or not members of the royal family watch the rendition of their lives on "The Crown," Princess Anne hasn't been afraid to admit that she took a peek at the show, albeit briefly. In 2020, a source close to Anne told Vanity Fair that the princess "has no interest in watching her life acted out onscreen." If the source was speaking the truth at the time, it might be safe to say that Anne's curiosity got the better of her later. In a 2020 documentary, Anne admitted to watching some of the show's first episodes. When asked what she thought of it, she had an answer typical of the kind her mother, Queen Elizabeth II, would have provided. "[It was] quite interesting," she said (via The Standard).

Anne also took the opportunity to crack a joke about the show, saying that she'd seen an article in Town & Country in which the actress who plays her, Erin Doherty, confessed that doing her hair for the show sometimes takes two hours. "The actress was talking about how long it took them to do their hair like I did. And I'm thinking, 'How could you possibly take that long?' I mean, it takes me 10 or 15 minutes," Anne quipped. You can add "professional hair stylist" to Anne's long list of accolades.

Aside from her many impressive equestrian achievements, Princess Anne was also nominated for a Nobel Peace Prize in 1990. She's long been known for her tireless work with charities. Her non-profit organization, The Princess Royal's Trust for Carers (renamed Carers Trust), aims to assist those looking after people who can no longer live independently. Anne's work with the Save the Children charity, however, is what got her nominated for the prestigious Nobel Peace Prize.

Zambia's former president, Kenneth Kaunda, nominated the Princess Royal. At the time, she'd already been serving as Save the Children's president for over 20 years while also being involved in more than 300 organizations and charities in her capacity as a senior member of the royal family. Kaunda found her work admirable. "She loves people. She has extended that love to working for helpless children in many parts of the world. That is love in action," the former Zambian president told BBC (via Deseret News).

The royal family has clashed with some U.S. presidents in the past, and the one that's caused the most controversy among the royals is — you guessed it — none other than former president Donald Trump. So when it appeared that Princess Anne blew him off while he met with Queen Elizabeth II, the story spread like wildfire across the internet.

In the now-viral video, Queen Elizabeth II is seen chatting with Donald Trump and his wife, Melania Trump, and then looking over at Anne, standing on the sidelines. The queen can be seen beckoning to her daughter; Anne looks at her mother and shrugs, with Trump and his wife looking on. Anne then cracks a smile but makes no move towards the president.

Naturally, everyone thought the brash Princess Royal was publicly blowing off Trump (we wouldn't blame her if she did), but it turns out Anne stuck to royal protocol for once, and this was not her taking a political stance. In fact, according to a source who spoke to Vanity Fair, remaining politically neutral has always been important to Anne, and she was upset by the allegations. What actually happened was that the queen asked Anne whether anyone else was lined up to meet her, and Anne shrugged and said, "It's just me and this lot [other members of the royal family]" (via The Guardian).

When Princess Anne takes a tumble, she does so in style — and she doesn't need anyone's help to get back up, thank you very much. An incident that occurred in 2007 spawned various headlines, some of them quite funny. "'Hands orf!' One can pick oneself up, says Anne," the Daily Mail headline read. Indeed, the Princess Royal was quite adept at getting up by herself after slipping and falling while visiting the island of Guernsey.

Anne was on a walkabout when she slipped and took a graceful fall. The bailiff, Geoffrey Rowland, who was next to her, dashed to her aid, and in the awkward scuffle that followed, Anne made it abundantly clear that she did not need his help. She got up alone, barely using her hands (read: she's got excellent core strength), and told Rowland to leave her be. "No, don't do that, thank you. Grabbing me round my (inaudible) won't help. I'm perfectly capable of getting myself up," Anne was heard saying.

Rowland later told the press that he was impressed by Anne's quick recovery, saying, " I offered her my assistance, but no damage was done. She was mildly shaken but swiftly recovered and was determined to continue with the walk through St. Peter Port. She was soon acknowledging bystanders in her usual relaxed and engaging way."

While the royal family needs to watch their tongues for obvious reasons, Princess Anne has managed the art of being both outspoken and respectful at the same time. Those who know her well say that much like her mother, Queen Elizabeth II, her dry wit is unmatched. "She's had me in stitches over some very naughty jokes," chairman of the Carer's Trust, John McLean, told Vanity Fair.

While visiting Moscow in 1990, Anne was asked what it was like to have Buckingham Palace as her private property. Anne chuckled and replied, "Well, I don't know because it isn't." This evoked several laughs from the audience before she continued to explain that the palace is owned by the state, not the royal family. Then there was the iconic moment when Anne and former Scottish footballer Denis Law were presenting the BBC Sports Personality of the Year award. Anne could be heard telling him, "You got this," as they took to the stage to present the award, but Law decidedly did not and forgot what year it was while starting the announcement. He pronounced 2019 as "the year of the two hundred and nineteen," and Anne quietly corrected him before looking heavenwards and scrunching up her face in disbelief. She also once comically described what royal engagements are like. "When I appear in public, people expect me to neigh, grind my teeth, paw the ground, and swish my tail – none of which is easy," she remarked (via The Standard).

Princess Anne is a doer, and when taking care of her hair and makeup for royal engagements, she often relies on her own skills to look striking. While Vanity Fair's reporter Katie Nicholl spent a day with Anne, she observed the Princess Royal quickly getting ready for public appearances. Not only did Anne do her own hair and makeup, but she also chose her own outfit with no help from a stylist. Anne is as independent as a woman in the royal family can be.

Anne can break the rules a little because she does her own makeup. While it's said that it's a royal protocol to steer clear of bright lipstick, Anne has sported a classic Taylor Swift red lip on plenty of public outings — and she's doing it right, too, according to experts. "She pairs her Hollywood glam bold lip with minimal other makeup, letting her freckles and clear complexion shine in contrast," makeup artist Saffron Hughes told Express. "Princess Anne's day-to-day appearance remains fairly understated, which means her lip adds an even more high-fashion edge." Clearly, Anne knows what she's doing. The same goes for her outfits — she's been praised for her fashion choices by none other than British Vogue editor Edward Enninful, who once dubbed her "a true style icon," telling Vanity Fair, "She is timeless in her style, and she wears a tailored suit better than anyone else I can think of."

Anyone who's been keeping tabs on Princess Anne over the years knows she's a fan of recycling her outfits and doesn't give a monkey's whether anyone notices. Anne has recycled some of the clothes she wore way back in the '80s, and she makes them work. "[She] was all about sustainable fashion before the rest of us really knew what that meant," British Vogue editor Edward Enninful told Vanity Fair. Anne makes a point of supporting local manufacturers, and fast fashion isn't something she spends her money on. "I still try and buy materials and have them made up because I just think that's more fun," she told Vanity Fair. "It also helps to support those who still manufacture in this country. We mustn't forget we've got those skills, and there are still places that do a fantastic job."
When it comes to choosing her clothes, Anne favors Harris Tweed because it holds up throughout her busy days. "For me, the point about it is that it looks exactly the same at the end of the day as it did at the beginning. Brilliant," she said. Anne chooses (and re-wears) outfits that are functional and comfortable. Hopping on helicopters and getting in and out of cars (and sometimes the London Underground) call for comfortable clothes, and Anne doesn't seem like the sort who would sacrifice comfort for style. It's no wonder she likes to choose her own outfits.

There are many things Princess Anne enjoys doing, but scrolling social media isn't one of them. In fact, the Princess Royal has never even used a social media platform — she's got people for that.
In the documentary "Anne: The Princess Royal at 70," Anne revealed that she's not a fan of social media at all, mostly because she's seen the pressure it puts on younger members of the royal family. She also doesn't think it truly connects people and believes that meeting individuals face-to-face is the best way to do things (and she's not wrong). "With online technology ... being in touch is one thing, but it's not quite the same. The ability to meet people, that's what makes the difference," she explained. "I know what Twitter is, but I wouldn't go anywhere near it if you paid me, frankly," she added.
Aside from all the extra pressure social media puts on those in the spotlight, Anne also isn't a fan of how these apps take up all people's time and attention. "I find it very difficult to understand why anybody gets sucked into screens and devices," she told Vanity Fair. "Life's too short, frankly. There's more entertaining things to be done. I suppose that puts me in the real dinosaur range."

One of the most fun moments in the "Anne: The Princess Royal at 70" documentary is arguably the scene in which we see Princess Anne helping her mother, Queen Elizabeth II, navigate Zoom. Anne may not be a fan of social media, but she's a pro when it comes to video conferences, and when the pandemic hit in 2020, the queen had to learn how to use it, too.

Anne, the queen, and a couple of other people met virtually to commemorate National Carers Week, and it was the first time the queen ever made a public video call. Anne was right there to help her mother navigate the Zoom platform, and shortly after the queen joined, Anne told her what she should be seeing on her screen. "Can you see everybody? You should have six people on your screen," she told her mother. "Yes, well, I can see four anyway," the queen replied, and Anne responded with, "Actually, you don't need me. You know what I look like!" This somewhat historic moment had people very excited on social media, and many took to X (then Twitter) to share how impressed they were with Anne teaching the queen how to use modern technology. "I truly love Princess Anne — such wit!" one person commented, while another quipped, "The Princess Royal can be summed up in one word. Splendiferous." (via The Independent). We couldn't have said it better ourselves.