Princess Beatrice's Style Transformation From Worst Dressed To Best Dressed

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 (via British Vogue). "So that's from being 18 and struggling with your weight to what fashion choices you are wearing." But the princess turned it into something positive. 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." 

Princess Beatrice was having a good run with her fashion looks in the court of public opinion when in 2017, she did something inconceivable. She stepped out in a semi-sheer dress held together only by a humble nude-colored slip. V&A summer parties over the years have seen far more sensational dresses than this one, but the stir Beatrice's dress caused can be pinned to her status as a royal. The British monarchy isn't exactly known for skin-baring dressing traditions and many social media users found Beatrice's outfit to be in serious transgression of that line. It's safe to say that the world, at least some of it, was not ready for the fabulousness Beatrice had unleashed on it. 

The princess is no stranger to rocking an outrageous outfit — despite the criticism that comes with it — but might have heaved a sigh of relief, knowing that at least some people were rooting for her. "This look kicked off the start of a real style evolution for Beatrice, now working with a stylist, she has truly found her sartorial elegance," fashion commentator Danielle Rogers-Clark told Express, noting that Beatrice had prompted the risqué Self-Portrait dress to sell out and even spawn dupes. Here was a royal family member unafraid to stray from traditions her other relatives wouldn't dare challenge and, if Rogers-Clark is to be believed, doing it all under the watchful eye of her grandmother, Queen Elizabeth II. 

Anna Wintour must have considered Princess Beatrice's fashion sensibilities worth something because in 2018, she scored an invite to the Met Gala — only the second British royal ever, after Princess Diana, to be given that opportunity. For Beatrice to be classified in the league of her style icon aunt was no small feat and the young princess made sure to live up to that honor with a smashing debut at fashion's biggest night. The theme that year was "Heavenly Bodies: Fashion and the Catholic Imagination" and her billowy gown, with its high-neck ruffles and ornamental detailing, more or less fit the bill. 

Otherwise known for her over-the-top style that would have blended right in with the Met Gala's disposition for outrageous fashion, Beatrice kept her ensemble ironically understated. But the simple-looking Alberta Ferretti gown supposedly held deep symbolism. History has shown that royals are deeply conscious of the power certain colors wield and seldom choose random shades to wear to important public events. The most obviously striking feature about Beatrice's gown was the color that dominated it — a regal purple commonly associated with royalty and widely interpreted as a nod to her blue-blooded heritage. The high-neck collar was also reminiscent of vintage royal fashion popularized by her ancestors like Queen Elizabeth I.

The trajectory of Princess Beatrice's fashion game can effectively be traced between Prince William's 2011 wedding to Prince Harry's 2018 wedding. While her outfit at one made her the target of mass ridicule, her turnout at the other earned her considerable praise, if not the best-dressed title. For Harry's nuptials, Beatrice went — first and foremost — easy on the headpiece, switching out squiggly designs for a simple headband-style accessory. It matched with her turquoise Roksanda Viola dress that, consistent with the festive mood of the occasion, was festooned with net and pearls. 

A year later at the wedding of her cousin Lady Gabriella, Beatrice diverged surprisingly far from the conservative royal stylebook and opted for a lace and bandage dress that was sheer in parts around her chest, midriff, and arms. While it didn't particularly qualify for one of Princess Beatrice's best looks, it sure proved one thing: she's a princess with spunk. She was also in peak form at the wedding of Crown Prince Hussein in Jordan, where she impressed in a blush-hued gown and a heirloom York tiara belonging to her mother. 

At her own wedding to Edoardo Mapelli Mozzi in 2020, Beatrice wore a widely-talked about vintage gown borrowed from Queen Elizabeth II's wardrobe. Never one to shy away from a recycled outfit, Beatrice's judiciousness made for a fashion moment that was not just sentimental but also iconic.

Few in the royal family can pull off a bold print like Princess Beatrice. While she still continues to reign over that particular corner of fashion, she's also simultaneously been leaning into a more sober color palette in recent times. Some of Beatrice's best looks in the years after her marriage have comprised monotoned dresses, pastel hues, understated headdresses — fashion symbols not previously associated with her. A striking case in point was the elegant powder blue dress she paired with a matching fascinator for the Thanksgiving service during Queen Elizabeth's Platinum Jubilee celebrations in 2022. Or the monochromic pink dress with billowing sleeves she wore to King Charles III's coronation a year later.

This inclination toward neutrality hardly means that Beatrice has discarded her printed outfits. If anything, that pile seems to be growing just as her newer fashion sensibilities are. But under the tutelage of her stylist Olivia Buckingham, she has been pulling those designs off with panache. A printed mini skirt she wore during an outing for Student Mental Health Week 2024, for instance, aligned wonderfully with the floral theme dominating 2024 fashion trends. It has not been easy, as Beatrice previously told British Vogue, to explore the world of beauty as a new-generation royal balancing her life both inside and outside the palace. "It's hard to navigate situations like these because there is no precedent, there is no protocol."

Who knew that beyond all those years of fashion gaffes and public criticism, there awaited a top spot for Princess Beatrice on Tatler's best-dressed list of people in Britain. Calling her the "Princess of Perfection" in its September 2024 issue, Tatler described her as "a beacon of sartorial elegance, pairing vintage-inspired cuts with fresh-from-the-catwalk glamour." True enough, Beatrice has not limited herself to a single signature style, constantly mixing styles to see what flies and what doesn't. Her unabashedly playful approach to fashion was evident most recently when she attended the 2024 Wimbledon matches in a color-specked shirt dress adorned with lace and florals that, despite its traditional cut and hem, exuded a blend of fun and sophistication perfect for the sporting event.

Such high praise for a public figure whose fashion journey has been an obstacle course of hits and misses was a welcome break from the narrative around her. But that very reason also led to questions being raised over whether or not the York princess really deserved to be called "the pinnacle of contemporary splendour." As public opinion raged on social media and television panels over the list — which also included the likes of Cruz Beckham — Tatler's style editor Chandler Tregaskes came out in Beatrice's defense, saying, "The true test of great taste is experimenting, learning from our mistakes à la mode, and coming back more fabulous than ever" (via WWD). We couldn't agree more!