The Most Inappropriate Outfits Princess Margaret Ever Wore

The British royal family is full of strict protocols, and Princess Margaret knew it. As the daughter of King George VI and younger sister to Queen Elizabeth II, Margaret spent most of her life immersed in all the trappings of royalty. In a way, this could all seem very glamorous. After all, Margaret was invited to all the wildest parties — which were, of course, attended by the brightest celebrities — and wore the most glittering jewelry. However, the flip side of the coin was that Margaret was expected to follow a strict royal dress code that encouraged her to sport pantyhose and prohibited her from wearing colorful nail polish.

If you think that this doesn't sound like a lot of fun, know that Margaret would have likely agreed. Over the years, the princess rallied against the restrictions placed on her royal wardrobe — so much so that she arguably pushed the bounds of fashion itself. Although these efforts ultimately made Margaret a style icon, they also caused quite a bit of scandal, both in her day and, retrospectively, in ours. From a pantomime costume that appropriated Middle Eastern cultures to a seminude outfit to a shabby getup that reflected poorly on the crown, these are Princess Margaret's most inappropriate outfits of all time.

Back in December 1943, World War II was ravaging Britain, and two of the sprightliest members of King George VI's family thought that Buckingham Palace was in need of some serious Christmas cheer. Cue Princess Margaret and her older sister, the future Queen Elizabeth II. The two girls decided to spread some joy by acting in a pantomime drama for the royal family's inner circle. The oeuvre of their selection? A version of "Aladdin" that came from the famous "One Thousand and One Nights."

While there was nothing inherently wrong with the princess' choice of drama, the same could not be said about their costumes. Dressed in loose skirts and baggy tops, Margaret and Elizabeth appeared to be wearing a version of Middle Eastern garb. Making matters worse, the pieces weren't necessarily reflective of the pieces that people in the Middle East actually wore. This means that Margaret and Elizabeth's outfits leaned more into the territory of cultural appropriation than appreciation. Although these concepts did not necessarily exist at the time of the pantomime, Margaret and Elizabeth's costumes did not age well. Decades later, these styles seem like a mockery of foreign traditions rather than a celebration of multiculturalism. 

While the young Princess Margaret likely did not intend for her pantomime costume to be scandalous in any way, the older Princess Margaret did seem to seek scandal at every turn. Her romantic life was a particular source of royal drama. From Princess Margaret's forbidden relationship with Peter Townsend to her complicated fling with Roddy Llewellyn, this fascinating royal seemed to flutter from one unusual love story to the next. Even her courtship with her future husband — the professional photographer Anthony Armstrong-Jones — did not lack its share of scandal. On one occasion in 1959, he made waves by shooting her in pearl earrings, a diamond necklace ... and apparently nothing else.

It's important to note that, originally, the idea was for Armstrong-Jones to capture Margaret on her 29th birthday. But the photographer loved scandal just as much as Margaret did, and it remains unclear whether or not she was wearing anything besides her jewelry during the photo shoot. Margaret's bare back made a striking appearance in the photo, and Queen Elizabeth II was said to have worried about how the shot would be received. After all, the British public did not wish to see the royal family engaging in antics that could be construed as morally questionable — and in 1959, the nudity of an unwed princess would have been seen as just that.

Princess Margaret and Anthony Armstrong-Jones did eventually decide to wed, and on May 6, 1960, they said "I do" at Westminster Abbey. Never one to bow to tradition, Margaret broke royal protocol on the day of her wedding by wearing a brand-new tiara to match her silk Norman Hartnell gown. While this may not seem like such a huge deal, the most committed royal watchers will know that, per royal tradition, Margaret should have selected her tiara from the official Windsor jewelry collection.

Instead, the princess settled on a piece that had once belonged to Margaret Harriet Beaumont — the wife of the 3rd Baron Poltimore. Princess Margaret purchased the item herself for £5,500 — a bargain compared to Princess Catherine's $135 million Lover's Knot tiara — and wore it proudly to her nuptials. As rebellious as this all may seem, however, it's likely that Margaret wore her tiara only with Queen Elizabeth II's blessing. After all, during her lifetime, the late queen reserved the right to approve or veto any wedding gown. Tiaras, likely, were also subject to her verdict.

Princess Margaret may not have been able to wear her wedding dress twice, but the same cannot be said about her tiara. Following her special day, the princess sported the sparkling Victorian-era item time and time again. Paparazzi photos of the princess in her car show that she wore the piece in both 1962 and 1965. Later, in 1977, the famous Poltimore tiara made a special appearance at an official state visit with Iran. Margaret's tiara, however, is not most widely known for its public appearances. After all, in 1962, she wore it in the bathtub, and her new husband, Anthony Armstrong-Jones, snapped a photograph. While this moment was meant to be private, it didn't stay that way forever.

In 2006, Armstrong-Jones shared the intimate portrait at an exhibition held at a London art gallery, and it didn't take long for the stunning image of the unclothed Princess Margaret to become an iconic representation of her life as a rebel. Unfortunately, however, Buckingham Palace would not have been pleased with the pictures of Margaret wearing nothing but her tiara. Nude photographs do, after all, go against royal modesty rules. And although Margaret had already died before the photos were released, the portraits were not universally well-received with respect to her memory.

In 1964, Princess Margaret posed for an especially fun photograph. Dressed in an 18th-century Georgian ballgown designed by Oliver Messel, the princess smized in a way that would have impressed the likes of the now-unrecognizable Tyra Banks. Holding a pen in her hand and gazing just beyond the camera, Margaret was a vision — just as she intended. She was, after all, headed to a period party that had been thrown for charity, and wanted her look to be perfect.

There was, of course, one major problem. It's best that members of the British royal family not dress up as historical royals. While this may seem counterintuitive, the reason is that they risk parodying themselves, and if the monarchy attracts laughter, we know that it's not being taken seriously.

Unfortunately, this was a reality that some of Margaret's nieces and nephews would discover a generation later. Indeed, in 1987, Prince Edward, Prince Andrew, and Princess Anne all appeared on the television special "It's a Royal Knockout." Meant to be a competition show that would raise money for charity, "It's a Royal Knockout" spun quickly out of control. Because the participants dressed in medieval-style garb as they rushed to complete a number of challenging feats, they seemed to be mocking their own royal identities. Decades later, the show remains an example of why outfits like the one Margaret wore back in 1964 should never leave royals' wardrobes.

Just because royals are expected to avoid historical outfits, however, doesn't mean that they should embrace any old trend. As members of an important national institution, royals must remember that they represent their country. This means that they must seek to embrace classic looks that transcend time — a metaphor, perhaps, for how the monarchy has survived throughout the centuries. Despite this, on one international trip, Princess Margaret shirked tradition by wearing a stylish strappy sheath dress and a trendy black headband.

To put things into perspective, the year was 1968. The place? Barbados. Accompanied by Anthony Armstrong-Jones, Margaret was attending an MCC party, and she was expected to greet members of a cricket team. But rather than wearing one of the more formal outfits her elder sister donned on tour, Margaret embraced all things casual. In other words, she wanted to participate in the fashion boom of the 1960s. She bared her arms in an era when this was not a usual part of royal fashion. Her earrings and headband encapsulated grooviness to the max.

The result was a version of Margaret that didn't look quite as royal as her blazer-wearing sister did. And if there's one thing that a princess should never be, it's less than regal. Ultimately, the princess' outfit was not appropriate for a woman in her position, even if she wanted to experience the excitement of the 1960s.

The strappy dress was not the only 1960s outfit that Princess Margaret donned on her 1968 adventures. On the same trip to Barbados, the queen's younger sister sported yet another arm-baring dress. This time, it daringly put her knees on display — another nod to the fashion trends of the 1960s. While this might not seem especially inappropriate, we must recall that for a royal to wear a skirt this short was rebellious, especially at this moment in time.

In fact, even years after Margaret showed off her knees, other royal women have tried to maintain tradition. Queen Elizabeth II was so steadfast in her efforts to resist the quickly evolving trends of the 20th century that she barely altered her wardrobe at all. Even 21st-century royals have followed suit to a certain extent. Princess Catherine has certainly embraced a style of her own, yet the instances when she bares her own knees are considered newsworthy. Ultimately, Margaret's short skirt was not appropriate for her role as a royal — even if it was totally fashion forward.

When Princess Margaret was photographed on religious leader Aga Khan's yacht in 1967, she looked like a celebrity. Dressed in a patterned frock and a large white pair of futuristic sunglasses, the princess looked like she belonged on Hollywood's red carpet. Sadly, though, that was the problem with her otherwise cutting-edge attire. Even if many fashionistas wouldn't have a problem with resembling the celebrity world's best and brightest, the same would not hold true for Margaret. The fact of the matter is that princesses are not supposed to resemble just any old famous people. If they do, it's believed that they will put the monarchy at risk.

Despite Margaret's choice of clothing that day on Khan's yacht, the princess was well aware of these dynamics. In fact, she was so aware of them that some of her acquaintances understood her to be a snob. On one occasion, Elizabeth Taylor was chatting with Margaret — when the princess took it upon herself to call the actor's diamond necklace "vulgar." Taylor, understanding Margaret's obsession with class and breeding, famously (via The Lady) put the jewelry around the princess' neck and declared, "Not so vulgar now, is it?"

But if Margaret felt that nonroyals shouldn't have been allowed to wear fine jewelry, she certainly didn't appreciate the flip side of that rule — that royals should avoid wearing celebrity-inspired attire. Thus, she broke protocol from time to time, even if it was not ideal for the monarchy's image.

British royals are expected to dress modestly, and although some royal family members have revealed too much leg on occasion, a bathing suit appearance would represent another level of scandal. Unfortunately, in 1976, Princess Margaret was photographed on the island of Mustique wearing just her bathing costume. And despite her reputation as a royal rebel, Margaret was hardly posing for the pictures. In fact, she was not aware that there were photographers surrounding her. She had spent years regarding Mustique as the place where she could hide from the prying eyes of the media. For paparazzi to capture her in such nonroyal attire would have been considered a massive invasion of privacy.

Fascinatingly, though, Margaret's outfit was not the main scandal to appear in the papers following the incident. Shockingly, the photographs at hand revealed that she was involved in an extra-marital affair with a young man named Roddy Llewellyn. At the time, Llewellyn was 25 years old and 17 years Margaret's junior. The public rushed to judge Margaret for what was viewed as a very unusual relationship — especially considering that most royal watchers were not aware of the sad state of her marriage with Anthony Armstrong-Jones by then. Thanks to these photos, though, when Margaret and Armstrong-Jones did part ways in 1978, few people were surprised. 

One of the British royal family's most important fashion rules dictates that lower-ranking members of the institution allow higher-ranking members to shine. This means wearing toned-down clothing that blends nicely into the background. As Meghan Markle, Duchess of Sussex, would later explain in the Netflix documentary "Harry & Meghan" (via Business Insider) "To my understanding, you can't ever wear the same color as Her Majesty, if there's a group event. But then you also should never be wearing the same color as one of the other more senior members of the family." With this in mind, Meghan opted to wear neutral colors that other family members wouldn't wear. Decades earlier, Margaret had a different approach.

This was made evident in 1981 when Margaret accompanied Prince Charles and Princess Diana to the movie premiere for the James Bond film "For Your Eyes Only." At the time, Charles and Diana were Prince and Princess of Wales — and some of the most important royals around. Because of this, Margaret should have selected an outfit that didn't overshadow Diana's. Instead, she opted for a red and gold frock that imitated the color scheme of Diana's own dress. Her choice prevented Diana from standing out in photographs — and made the People's Princess look like just another royal. Given the rules at hand, Margaret's choice of attire was incredibly inappropriate.

The 1981 movie premiere would not be the last time that Princess Margaret selected an outfit that competed with Princess Diana's fashion choices. In 1990, both princesses would attend the Battle of Britain parade wearing similar colors. While Diana wore a lime green blazer dress, Margaret selected a sea green dress that she wore over a collared shirt. Once again, the ultra-vibrant shade chosen by Queen Elizabeth II's little sister risked upstaging the Princess of Wales.

Interestingly, there may have been a reason fueling Margaret's rebellious choice. Princess Margaret and Princess Diana's relationship started out well but progressively disintegrated over the years. When Diana first joined the royal family, Margaret supported her — even justifying the newly minted princess' right to skip family get-togethers. Things changed, however, after Prince Charles and Diana's marriage began going south. According to Andrew Morton's 1992 biography, "Diana: Her True Story" (via Town & Country), Margaret would complain about Diana to her friends, bemoaning, "Poor Lilibet and Charles have done everything they can to get rid of the wretched girl, but she just won't go."

In August 2001, the royal family organized a photo shoot to celebrate the 101st birthday of Queen Elizabeth, the Queen Mother. Both of Elizabeth's daughters — Queen Elizabeth II and Princess Margaret — were expected to attend. Unfortunately, though, the event took place at a moment when Margaret's health was rapidly declining. Rather than dress up for the occasion, the elderly princess appeared in an unbuttoned sea green blazer and an untied floral scarf. The least attractive part of her outfit, however, was probably a camel shawl that was draped over her lap and had bunched up around her ankles. Her attire could not have been less indicative of the royal icon she had always been.

While most families would not think twice about an older member spotted in cozy clothes, the royal family is not your typical family. For Margaret to be seen dressed in less-than-spectacular clothing was a strike against royal tradition. According to protocol, she shouldn't have been photographed in anything less than haute couture. One source close to the queen later told the Daily Mail, "It's a haunting image and not one the queen remembers fondly." Apparently, the issue was that Margaret became a subject of conversation — and not in a good way. As another insider told the publication, "The optics were terrible ... all anyone saw was a sadly declining Princess Margaret." At the very least, this was probably not how Margaret wanted to be remembered.