The Most Infamous Fashion Flops In Royal Family History

You'd think it would be easy to look great all the time as a member of the British royal family. With money being no object and designers falling over one another to dress you, what could possibly go wrong? A lot, as history has taught us. Privileged as they are, the royals are still humans subject to the same mistakes as us commoners — and that goes for their fashions, as well. 

Many are the times a member of The Firm appeared in an outfit that went against all common sense, or which represented the worst of the era's trends. On other occasions, a poor fit, an overlooked detail, or a food spill left a royal looking less than their best. And while no one in the family has done a complete "Emperor's New Clothes," some have accidentally revealed more than was proper when a gust of wind or a too-sheer fabric did them in.

We've collected some of the most famous fashion flops the palace has ever produced, with apologies for any cringing it may induce. On the other hand, seeing the worst-dressed members of the royal family might make you feel better about your own wardrobe: "At least I never went out in anything like that."

We hope she at least enjoyed the dinner! On June 2, 2010, Queen Elizabeth II and Prince Philip attended a dinner honoring King Constantine II of Greece on his 70th birthday. (Philip was the king's father's cousin.) As the guests departed, cameras caught the queen in an awkward situation: Not only were there very visible stains on her aqua dress, but the chain handle of her silver purse had also snapped, leaving the monarch literally holding the bag.

All eyes were on Princess Diana's wedding gown when she exchanged vows with then-Prince Charles on July 29, 1981. The stunning silk taffeta confection by David and Elizabeth Emanuel featured a 25-foot train. Yet as iconic as the dress was, its massive size and fussy details (those ruffles! Those puffed sleeves!) overwhelmed the princess's delicate frame. The fabric was also ill-suited for the bride's traditional carriage ride to the cathedral. Royal embroiderer Chloe Savage told Business Insider, "It looked like it needed to be pressed."

More than 15 years and three children later, people are still talking about the worst-dressed royals at the wedding of William and Catherine, Prince and Princess of Wales. Topping the list were the groom's cousins Princess Beatrice and Princess Eugenie. While fascinators are de rigueur at formal royal events, the sisters' outlandish hats took the tradition too far. On the plus side, Beatrice later auctioned off her pretzel-y topper for charity, where it sold for $130,000.

Meghan Markle, Duchess of Sussex, was glowing in the early months of pregnancy when she and Prince Harry, Duke of Sussex, visited the island of Tonga in 2018. Her red $540 Self Portrait dress was both gorgeous and economical by royal standards. Unfortunately, the duchess forgot to do a mirror check before leaving the house; otherwise, she might have noticed the care tag was still attached to the hem. Meghan changed outfits later in the day, but not before the press had a good chuckle over the relatable mishap.

Then-Duchess of Cambridge Kate Middleton was stunning as she walked the red carpet with Prince William at the 2018 BAFTA Awards, the British equivalent of the Oscars. Her deep green gown flattered both her complexion and her baby bump (she was expecting Prince Louis at the time). However, this was the year that the celeb women were all wearing black in solidarity with Time's Up, a movement supporting workplace equity. The future princess caught a bit of flak for seemingly ignoring the dress code, though royals are expected to stay politically neutral.

Maternity wear seems to be a stumbling block for the royal moms. In 2013, pregnant with firstborn Prince George, Kate Middleton visited a Hope House children's hospice. On the way over, her Max Mara wrap dress came untied, necessitating a quick adjustment as she left her limo. Other photos from the day show Kate often keeping her hands in front of her. Was she cradling her baby bump, or just making sure her dress didn't fly open unexpectedly? Perhaps both.

Just a few weeks before her wedding, Lady Diana Spencer attended the 1981 Royal Ascot. For two of the days, she wore demure, understated dresses; one was a gray gingham that looked like something from "Little House on the Prairie." Then there was her other outfit: an oversized red-striped shirt with a wide ruffled collar and bow, paired with a red skirt, a long red vest, a hat, and white gloves. All Diana needed was a red nose and oversized shoes to complete the clownish image.

Hats make a statement at British royal events, but Queen Camilla's hat at the 2007 Trooping the Colour ceremony said far too much. The then-Duchess of Cornwall wore a perfectly lovely gold silk suit, yet decided to match it with a wide-brimmed feathery topper which looked as though several chickens had imploded on her head. Even Princess Eugenie and Prince William seemed to have trouble viewing the military parade around all the fluff. It was truly one of Camilla's worst-dressed moments of all time.

As if Meghan Markle didn't have enough troubles with her public image, another 2018 appearance was even more embarrassing. As she greeted a swarm of fans in New Zealand, the light caught her blue and black skirt and seemed to render it more than a little revealing. Of course, no one would have dared alert the fail to a member of the royal family — not that Meghan could have done anything about it right then, anyway.

Racing fans prone to migraines must have been dismayed at seeing Anne, the Princess Royal, at one particular appearance of the multi-day 2026 Royal Ascot festivities. The annual event calls for jolly fashions and perky hats, and normally the princess leads the way with her smart wardrobe. This time, however, she wore a coat dress featuring an overly busy pattern that could have come straight from Carnaby Street or Haight-Ashbury in the '60s. It was bold, but not the most flattering look.

When visiting abroad, royals have to be careful to honor their host countries, which is why Prince William and Kate Middleton's outfits (seen above) were a headline-making gaffe. Arriving in the Solomon Islands on a 2012 Asia-Pacific tour, the future king and queen found the clothes in their room and wore them to dinner. Only later did they learn that the dress and shirt were gifts from the Cook Islands and not the outfits they were meant to wear. Red faces and official apologies followed.

Attending the London premiere of "Beverly Hills Cop II," Sarah Ferguson stood out in all the wrong ways. Yes, it was 1987. Yes, neon colors, sheer overlays, and big hair were all the rage. Yes, the former duchess is known for being spirited and unconventional. But even so, this look was a lot, and almost had the air of a Halloween costume. Fergie is the mom of Princess Beatrice and Princess Eugenie, who each have daughters of their own. Imagine the sisters showing this photo to their girls and saying, "That's your Gram!"