40 Vintage Photos Of Princess Anne That Offer A Rare Glimpse At Her Remarkable Life

If there’s one topic with which the Princess Royal is most associated, it’s horses. She obviously loves them and has been riding since a very young age. This picture shows her on a horse named Purple Star at the Eridge Horse Trials in 1968. But Anne's most famous equestrian partner was Doublet. This thoroughbred cross gelding once belonged to her mother, Queen Elizabeth II, and Anne rode Doublet to gold-medal glory at the European eventing championship in 1971.

Anne was never afraid to take fashion risks. While attending a fashion show in Brisbane, Australia, in 1970 she opted for a large hat with a decorative bug on it. It looked terrific, plus that artificial insect may have helped to distract the public from Princess Anne's slip-up during this royal visit. While she was in Sydney, you see, the Princess Royal reportedly complained about the "bloody wind" — and many old-fashioned Australians were shocked to hear such language from a royal family member!

Here’s an occasion where three royal women color-coordinated to great effect. When attending the investiture of Anne’s brother, the future King Charles III, as Prince of Wales in 1969, she, Princess Margaret, and the Queen Mother all wore brightly-colored outfits and hats. Charles' brothers — Prince Andrew and Prince Edward — were not at the engagement, reportedly because they were two young. This event — and these incredible outfits — were memorably recreated during season three of The Crown.

The wedding of Charles and Lady Diana was a massive occasion, and it merited a massive hat. Anne chose this incredible yellow creation, plus a white floral dress by Maureen Baker. Society magazine Country Life commented, "Princess Anne's dress was one of the prettiest she has worn in public. The yellow silk cap trimmed with yellow and white flowers by John Boyd was also one of the most attractive in church." And the practical princess wore the exact same outfit 27 years later at the wedding of Lady Rose Windsor.

Anne’s daughter, Zara Tindall, absolutely followed in her mom’s footsteps when it came to sports. Here’s mother and daughter together at the Cheltenham Races in 2000, just as Zara’s own equestrian career was about to take off. Zara won the Eventing World Championship in 2006 and took home a silver medal as part of the Great Britain Eventing Team at the 2012 Summer Olympics. At the latter event, Princess Anne got to present her daughter with the Olympic medal.

One big perk of being a royal is meeting so many famous bands and musicians. Anne met the Scottish pop band Bay City Rollers at the Lyceum Ballroom in 1975 during the Carl Alan Awards. This award show is one of the most prestigious nights on the calendar for professional dancers. Here, the Princess Royal dressed in a lovely marigold-colored ball gown for the occasion. The band members unsurprisingly look pretty awestruck in her presence.

UNESCO announced that 1979 would be the International Year of the Child. There were many events throughout the year to promote the importance of child welfare, and the royal family made it a point to attend The Great Children's Party in Hyde Park in May of that year. Anne, who has always been really good at putting together one-color ensembles, attended in an all-orange tangerine coat and a perfectly matched toning headscarf. She also chose an eye-catching golden brooch in the shape of a seahorse. None of it should work, but it really does.

British royal jewelry is a serious, serious business. Some are extremely controversial and some are just extremely beautiful. Princess Anne is wearing the Meander Tiara in this 1988 photo taken during a Guildhall banquet. It's a stunning piece that was passed down to the royal from her grandmother Princess Alice of Battenberg. You might have also seen it on Zara Tindall’s head at her wedding since her generous mom lent it to her for that occasion.

In this photograph from 2008, Anne is issuing her nephew Prince Harry with the Operational Service Medal in recognition of his military service in Afghanistan. Both parties look like they’re quite enjoying the occasion, and that's always nice to see. The pair also made headlines after King Charles III's coronation in May 2023. Anne was one of the only working members of the royal family pictured talking to Prince Harry during that event — and they still seemed to share a sweet bond.

Anne looked seriously stylish in a blue shirt and neck scarf while in Kyiv, Russia, in 1973. She was in the Soviet Union to compete in the European Horse Trials. Unfortunately, the trial did not go well as the Princess fell from her horse during the event. "The 23‐year‐old Princess got up and refused to board an ambulance," The New York Times reported. "She limped one‐quarter of a mile back to the starting point."

This photo of a smiling Anne and Mark Phillips was taken in the runup to their wedding in 1973. Unfortunately, as you may already know if you're an Anne stan, their marriage didn’t last. They had been separated for years before the palace made an official announcement on the matter in 1989. The pair finally divorced in 1992 — a year after it was confirmed that Phillips had fathered a child with another woman while still married to the royal.

Yes, that really is Princess Anne and her brother, King Charles III, holding hands in Malta in 1954. Anne would have been just three-and-a-half years old at the time, while Charles would have been a stately five and a half. The young royals had traveled over to Malta to meet their parents — Queen Elizabeth II and Prince Philip — who had been on an extended tour of the Commonwealth. No doubt the late Queen was delighted at her children's outfits!

This photo shows Anne standing next to her mother, Queen Elizabeth II, at a formal event during a state visit to Austria in 1969. The princess is wearing the Meander Tiara, her royal regalia, and a pretty white dress. The family resemblance is very apparent in this image — although Anne was not as popular with the public at the time. A 1989 article in the Chicago Tribune reported that Anne was "once an arrogant and unpleasant teenager whose poutiness made her the most unpopular member of the royal family."

In 1969 members of the royal family, including Anne, filmed a documentary for the BBC about their everyday lives. It was called simply Royal Family, and it was watched by about 30 million people in the U.K. alone when it first aired. But the documentary went down in history as a major misstep after the palace reportedly encouraged the BBC to leave it in its archive. Royal Family hasn't been broadcast since 1977. The Princess Royal herself was apparently never a fan. "I thought it was a rotten idea," she said, according to the book Queen Elizabeth II and the Royal Family.

In 1972 Anne went with her parents to visit the royals of Bangkok, Thailand. It was a glittering affair, with plenty of fine dresses and tiaras on display. But the outfit that Queen Elizabeth's daughter wore — a patterned dress and matching hat — was a real standout. The whole photograph is a tour de force of royal fashion. And the three royals would later continue their state visits in Singapore, Malaysia, Brunei, the Maldives, Seychelles, Mauritius, and Kenya.

In July 1972 Anne met the famous French mimic Marcel Marceau at a gala in London at the Sadler’s Wells Theatre, where Marceau often appeared. The royal looked somewhat perturbed in this photograph — but perhaps we shouldn't be surprised that she was letting her emotions show. It was around this time that Anne was being called "aloof" and "haughty" by the press, which also labeled her "her royal rudeness." It would be a few more years before she could turn her reputation around.

Anne was seen smiling happily as she attended a Royal Ascot Race meeting in June 1969. It's hard to tell in this image, but the weather was not good at the time. Still, as the original caption released with this photo stated, she managed to wave and “made a charming companion for her escort, the Duke of Beaufort.” And, for our money, the senior royal was the star of the show, as was her patterned jockey cap.

One important royal duty is inspecting the guards at various events. Here, an 18-year-old Anne was making sure the soldiers were spick and span in 1969 at the Festival of London Stores Parade. Anne herself was immaculately turned out in a neat coat dress, a fashionable cowboy-style hat, and statement white gloves. Fun fact? Queen Elizabeth II's first official public engagement was, when she was 16 years old, inspecting the Grenadier Guards at Windsor Castle in 1942.

Most pictures of Anne show her with her hair up, but she obviously looked great with it down too. Here, she was rocking that look at the Badminton Horse Trials in April 1971 at the age of 20. She rode Doublet, the horse given to her by Queen Elizabeth II, and came in fifth. Her eventual husband Mark Phillips won that competition — but it was Anne who won over the British public. She was voted the BBC Sports Personality of the Year for 1971, after all.

The princess brought some great fashion pieces to even relatively minor events, such as this village fete in 1975. It may seem odd that a member of the royal family should attend a fete in a village with just 450 residents — but if you dig a little deeper, it makes sense. The village in question was Great Somerford — probably best known to the world as the hometown of Mark Phillips, Princess Anne's first husband.

In this picture from December 2017, Anne wore her smart military outfit at the Commissioning Ceremony of the boat HMS Queen Elizabeth. The Princess Royal is one of the few royal women who gets to wear military uniforms and medals at ceremonies. Even though she has never actively served in the military, Anne holds the rank of Admiral and is the Chief Commandant of Women in the Royal Navy. She's also a General in the British Army and an Air Chief Marshal in the Royal Air Force.

When attending a 1984 banquet in Dubai, Anne wore this lovely light-blue evening gown that swept down to the floor. Her brooch is of particular note, though. That’s a copy of a sapphire brooch Prince Albert gave to Queen Victoria before their wedding, so there’s a lot of British royal history tied up in it. Anne is especially known for wearing meaningful brooches to royal events — with some estimating that her brooch collection is worth thousands.

For Trooping the Color in 1980, it seemed like the whole royal family decided to wear yellow. Anne has selected a sensible dress coat tied with a gold belt, plus a matching hat and some stand-out pieces of jewelry. And she would go on to wear that same coat to many other events over the years. She first pulled it out of the closet for the Epsom Derby in 1983 and then wore it again to Royal Ascot in 1991, 2011, and 2015.

Anne visited Nairobi in 1971 to meet orphaned youngsters at the Starehe Boys’ Centre. The school was partly built by Save the Children — which the princess was then the president of and is now the patron. "I am proud of my long association with Save the Children, and I am honored to succeed Her Majesty as its Patron," Princess Anne wrote in 2020. "It is an organization that embodies a spirit of compassion, openness, and excellence. Its values are an inspiration; its achievements, a source of hope for millions of children."

The close bond between Queen Elizabeth II and her daughter, Princess Anne, was always front and center whenever they appeared in public. This is evident even in this picture from when the Princess Royal was barely two years old. In May 2023, Princess Anne opened up about their relationship with Canada's CBC News. She said, "The relationship tends to remain if you are lucky very similar throughout your life." She was also touched by the amount of people who turned out to pay their respects after the Queen passed away.

Anne is seen here on her 1971 trip to Kenya, visiting Treetops Lodge in Aberdare National Park. But perhaps because she was surrounded by people taking photographs of her, she didn't look very happy about it. Like many members of her family, after all, the Princess Royal has never been a fan of having cameras shoved in her face. In fact, she once famously told a photographer to "naff off" after falling from her horse.

Anne and her fellow royal women — Princess Diana and Elizabeth, the Queen Mother — are absolutely dressed to the nines at this film premiere in 1985. They were going to see David Lean’s A Passage to India, but they would have fit in perfectly at a royal wedding as well. The presence of Princess Anne at a movie premiere wouldn't have come as a surprise at the time. She was the president of the British Academy of Film and Television Arts from 1972 to 2001.

Anne and her mother, Queen Elizabeth II, seemed to be having fun here as the monarch cut a cake celebrating International Women’s Day in 2004. The late Queen wore bright purple — she usually opted for bright colors — but Princess Anne chose a stylish military-style dark green jacket with red buttons. Queen Elizabeth II also hosted a women-only luncheon at Buckingham Palace to mark the occasion — and of course her daughter was there to celebrate with her.

Maybe one of the reasons Anne became an equestrian was the sheer style of traditional dressage outfits. Okay, that’s probably not the reason, but there’s no denying they always suited her perfectly. Here the young princess is representing her home country at a three-day Ukraine-based competition in September 1973. We know, of course, that she would later take a tumble from her horse during the event — but that didn't stop her from riding horses for years afterward.

Anne’s daughter Zara married rugby player Mike Tindall in July 2011. The mother of the bride looked incredibly happy on her daughter’s big day, too. But she didn’t let sentimentality get in the way of her recycling the outfit! She wore the same pink florals to Royal Ascot the very next year. Edward Enninful, the editor of British Vogue editor, told Vanity Fair in 2020, "Princess Anne is a true style icon and was all about sustainable fashion before the rest of us really knew what that meant."

Queen Elizabeth II celebrated her Silver Jubilee in 1977 and of course, her only daughter was at her side. Check out Anne’s incredible headpiece, which matched her blue coat. Oh, and the princess was actually pregnant with her son Peter during this occasion as well. This event took place in June, but the Silver Jubilee was actually celebrated in church services in February 1977 and then commemorated with numerous engagements throughout the year.

In 1984 Anne visited Gambia to do charity work for Save the Children. She had been working for the charity for a long time already by this point — and was really starting to come into her own. "It took me probably 10 years before I really felt confident enough to contribute to Save the Children’s public debates," she told Vanity Fair in 2020, "because you needed to understand how it works on the ground and that needed a very wide coverage. So my early trips were really important."

The dress the princess wore for her wedding to Mark Phillips was a much-discussed one. It was a white silk number dreamed up by Susan Small designer Maureen Baker and inspired by Queen Elizabeth I and the Tudor era. Some people love it, some people hate it, but it fitted in perfectly with Anne’s unique style. She was the first of Queen Elizabeth II's children to get married — and, interestingly, she was the first to get married a second time, too.

Like mother, like daughter. Queen Elizabeth II and Anne had exactly the same expressions on their face — and very similar outfits — as they watched a horse race in Surrey in 1988. Both women have shared a lifelong love of horses, though, of course, it was only the princess who was able to pursue 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,” Princess Anne told Vanity Fair.

Anne probably has a whole wardrobe of bright colors, but yellow seems to be the one she likes the best. She wore a yellow cardigan and hat over a patterned dress while attending Sandhurst Military Academy. And true to form, the Princess Royal would recycle that dress eventually. Eleven years later, she had it lengthened and wore it in Dubai. “She is timeless in her style, and she wears a tailored suit better than anyone else I can think of,” told Vogue.

It’s not every day you see a royal land in mud, but that’s what happened when Anne’s horse failed to successfully clear a water jump during the Badminton Horse Trials in May 1982. This was the fall that saw Anne, after being asked about it by photographers, famously telling the press to “naff off.” Although some people have since claimed that the media used the word "naff" because the word the Princess Royal really used was unpublishable.

In this photo, princesses Anne and Diana stood next to each other during a remembrance ceremony at the Cenotaph in 1984. It has long been believed that the two women never really got along. But there is an interview in which Diana seemed to disprove this rumor. When asked whether Diana was feeding with Anne, Diana said, “Princess Anne has been working incredibly hard for the Save the Children Fund, and I'm her biggest fan because what she crams into a day I could never achieve.”

James Beaton was Anne’s bodyguard, and he intervened when a man attempted to kidnap her from her car in 1974. Beaton was injured in the attack, but thanks to the efforts of him and others the royal’s assailant, Ian Ball, was stopped in his tracks. The guardian was taken to Westminster Hospital, where the princess visited him, and later received a George Cross medal. The best part of the story? When Ball told Anne to exit her vehicle, she told him, "Not bloody likely!"

When Britain began preparations to host the Olympic Games in 2012, Princess Anne was the representative who received the all-important Olympic flame during the handover ceremony in Athens. That was very fitting since the princess was the first British royal to actually compete in the Olympics herself. Oh, and she’s President of the British Olympic Association. The Princess Royal has continued to support Great Britain in all of the Olympic Games that have followed, too.

In this picture from Germany in 1969 Anne is learning how to drive a tank. And there’s no reason to think she wouldn’t learn fast. In 2020 she commented to Vanity Fair magazine that if she hadn’t been born a princess, she might have liked to be an engineer. "The practicalities of how things work, I think, was always interesting as far as I was concerned," she said. She later added, "I've certainly enjoyed being part of trying to encourage more girls to look at engineering as a realistic career."