Princess Beatrice’s Fashion Journey: From Worst to Best

Princess Beatrice hasn’t exactly had the smoothest ride as a fashion icon. She’s been toeing the line between experimental and eccentric ever since she came into the spotlight as a key member of the British royal household, her journey on loud and proud display for the world to see. It can’t have been easy and, as the York princess herself has testified, being a public figure brought with it scrutiny over the most personal aspects of her life.

“My experience was about growing up and living a very public life and living in an overexposed environment,” she said during a House of Lords event in 2017. “So that’s from being 18 and struggling with your weight to what fashion choices you are wearing.” Even when she was infamously hauled over the coals for a harmlessly bizarre hat she wore to a royal wedding in 2011, Beatrice used the moment as an opportunity for charity and put her ridiculed accessory up for auction.

While her taste in fashion still hasn’t convinced a lot of people, Beatrice has quite a few fashion authorities on her side. “I think Beatrice has a good eye; she’s been wearing some fabulous pieces over the last few years,” Beatrice’s former stylist Charlie Anderson told People. Further cementing her place as a fashionista is a best-dressed list that the princess topped in 2024. Scroll on to see Princess Beatrice’s full style transformation.

Like everyone else who got swept up in the zeitgeist of the 2000s, Princess Beatrice really leaned into an over-the-top wardrobe that defined the era. She was entering her teens just as the new millennium started; the timing couldn’t have been more perfect to experiment with all kinds of rebellion. A pair of boots she wore to the royal family’s Christmas service at Sandringham in 2003 summed up her sensibilities best — bejeweled, floral, knee-high, and a complete mismatch with the rest of her outfit. It was peak Y2K fashion. From ruffled dresses to chunky belts and strappy heels, Beatrice indulged in every trend the noughties were notorious for.

As teen years usually do, the period also brought significant unease into Beatrice’s life. In a 2008 incident that was infamously nicknamed “Bikinigate,” Beatrice was photographed holidaying in St. Barts in a swimsuit that resplendently showed off her curves, leading to intense public scrutiny over her weight. “She was young and I don’t know any 18-year-old who has not had a bad photograph taken of them,” her trainer Nadya Fairweather told Express, disclosing that the incident stirred Beatrice to undergo a transformation on the grounds that she would always be a media figure. Princess Beatrice’s weight loss journey became most apparent as she stepped out in form-fitting dresses with cinched waistlines and short hems — the ultimate party girl uniform of the 2000s.

Princess Beatrice was a mad-hatter all through the aughts. Her penchant for campy headdresses was evident as an early feature of her fashion tastes as a teen royal, offering audiences a glimpse into the exciting hat-heaped future that awaited her. Beatrice is not the first, and certainly not the last, member of the monarchy to indulge in eye-catching headpieces. The British royal women — all the way from Princess Diana to Queen Elizabeth II — are known to have served hat looks that have gone down in the pages of fashion history. Come to think of it, Beatrice has, in a way, only been prolonging her family’s hat-wearing legacy by giving it the due it deserves — albeit in ways that may have been a bit too quirky at times.

Flowers and feathers and other natural elements remained steady trademarks of some of Beatrice’s earliest headpieces that made audiences sit up and take note. The butterfly headdress she wore to her cousin Peter Phillips’ wedding in 2008 is an all-time iconic piece and captured well the extravagance that symbolized Beatrice’s style. Other royal events like Trooping the Colour and the Royal Ascot gave viewers some more gold moments. Notwithstanding the fun royal women have with them, these accessories are more than just showpieces. They are a time-honored tradition. As fashion journalist Hilary Alexander told ABC News, “There has to be a hat, it’s part of the social fabric.”

The year 2011 was a turning point in Princess Beatrice’s life. Up until then, she had been a relatively inconsequential player in the royal fashion game. Prince William and Princess Catherine’s wedding turned her into an overnight celebrity — though not to the most flattering effect. Beatrice showed up to the royal ceremony, which was watched online by a record 72 million viewers, in a headpiece that can only be described as outlandish. For those who need a memory refresh — although that would hardly be necessary, since it was a royal fashion moment impossible to forget — it was a beige bow-shaped squiggle that rested most peculiarly on Beatrice’s forehead.

Memes and trolls swooped down on the princess almost immediately and her fascinator became a viral internet joke. Her sister Princess Eugenie and her feathered hat were not spared either. “There was a moment where I thought I would find myself with my head on a spike outside the Tower of London,” Philip Treacy, the royal milliner behind Beatrice’s pretzel hat, said on BBC Radio 4 following the mass disapproval. Beatrice herself seemed to be more easygoing about it all, unafraid to voice her appreciation for the headdress, and put it up for a charity auction. Notwithstanding her benevolent reaction, it was evident that Beatrice’s public image was in dire need of a revamp and, per People, celebrity stylist Charlie Anderson was brought on board for the task.

The 2011 fashion gaffe may have prompted a wardrobe refresh for Princess Beatrice but it hardly deterred the royal from indulging in her trademark quirky style sensibilities. Bold prints and vibrant accessories continued to dominate her lookbook, making the princess impossible to ignore at any event she attended. Consider, for instance, her appearance at the Epsom Derby races in 2013. Beatrice stood out from the rest of her family — most of whom had opted for muted colors for the daytime gathering — in an eye-catching black and white dress with huge graphic prints. This she paired with a maroon hat that, though not comparable to her 2011 headpiece, was a dramatic statement in itself.

Next year, she showed up for a summer party at the Kensington Gardens in yet another striking dress covered in 3D flower detailing that, true to theme, gave her the look of a flowerbed. Clearly, she had a thing for florals. As her ex-stylist Charlie Anderson would come to tell People later, Beatrice’s style transformation only “got more daring” with time, especially considering that she grew into her own as a woman with independent sartorial choices. She was no longer the 22-year-old with the funny pretzel hat. Audiences may or may not always have loved the flashy patterns and loud prints that Beatrice evidently developed an even stronger taste for, but her unwavering dedication to her personal style sure did invite praise for her self-confidence.

It seems that having a personal style instructor by her side to navigate the crosshairs of public opinion on fashion did Princess Beatrice quite a bit of good. In the years after Prince William’s wedding put her into the spotlight, with her style receiving greater coverage than ever before, the York royal’s wardrobe underwent an evident upgrade. Flattering silhouettes and sophisticated prints replaced boxy dresses and overbearing patterns, taking Beatrice’s score of fashion hits to a new high.

A dress she wore to the Royal Ascot in 2015, which featured soothing greens, blues, and color-accented graphics, was a fine example of the transformation she was trying out. The memorable dress made a delightful return nearly a decade later when Beatrice, ever the prudent princess, recycled it for a Wimbledon afterparty. She also leaned into more contemporary classics during this era, a tux-style black gown she wore to an Alexander McQueen gala that same year standing out in her increasingly experimental lookbook.

Around this time, the general sentiment around Beatrice’s style also softened, with opinions in the media defending the princess from the harsh criticism she was often faced with. A piece published by the Independent in 2016 eulogized Beatrice’s fearless fashion sense. “It’s time there was some life injected into the Royal wardrobe,” the article mentioned, noting with some certainty that Beatrice and her sister Princess Eugenie were “the fashion messiahs we’ve been waiting for.”