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In the drama-packed telenovela that is the House of Windsor, you can be riding high in April, shot down in May, and plummeting in popularity at the flip of a dime. However, some things remain constant: the shady side of Prince Andrew, Duke of York, the bloated sense of entitlement, the ludicrous rules that accompany hobnobbing with royals, the archaic customs and antiquated beliefs, and last but not least, Princess Eugenie of York’s tasteless style. The latter is, quite possibly, the biggest royal disaster of all, even overshadowing the cringeworthy interview where her father, Andrew, spectacularly failed to explain away and justify his friendship with convicted pedophile Jeffrey Epstein. OK, maybe not. Nowhere near, in fact. Still, Eugenie’s fashion felony rap sheet is a catastrophe that hasn’t gone unnoticed.

Despite her highly questionable clothing, Eugenie has undergone quite a transformation. She’s left her awkward teens behind her and become a wife, mom-of-two, successful art gallery director, and passionate activist. But the royal family persistently snubs Eugenie and her sister Princess Beatrice of York — and it has nothing to do with horrific headwear or ghastly garb. Sadly, it seems the siblings’ utterly unforgivable offence is being born to Andrew and his now ex-wife, Sarah, Duchess of York.

Undoubtedly a problematic and gruesome twosome if ever there was one, but then, you don’t get to choose your parents. That said, you do get to choose your outfits, which makes Eugenie’s appalling attire all the more puzzling. We’re checking out her tasteless style and the social shade it sparks.

Princess Eugenie’s tasteless style was on full display in March 2009 when she attended “The Young Victoria” world premiere in London with Princess Beatrice of York and Sarah, Duchess of York. Eugenie was clad in what resembled a nightgown and net curtain combo, paired with gladiator-style sandals, resulting in a look that was nothing short of a right royal disaster.

Still, Eugenie and her equally style-stunted sibling were keen to show off their Alice Temperley designer duds — reportedly shaking their thang on sofas while out clubbing with their mom. Fashion fans were few and far between, though.

“[Eugenie’s] shoes were too clumpy and not strappy enough, and the pleats of the double-layered dress just make it look cheap — as does the fabric, particularly under the flash lights of the camera,” stylist Miranda Holder critiqued in a July 2023 Daily Mail interview.

Princess Eugenie’s girls appeared to proudly stand to attention when she posed for pics during day one of the Royal Ascot festivities in June 2019. Sadly, however, the royal wasn’t vying to be the next #FreeTheNipple advocate. Instead, the poorly placed darts on the chest of her dress resulted in her putting on a frocky horror show for the public.

It’s pretty safe to say it wasn’t the look Eugenie aimed for. The unflattering pleats on her $2,200 teal-colored, yellow-panel Calvin Klein dress and the hat that resembled a flat pancake she had stuck on her head did absolutely nothing to up Eugenie’s attire game.

“Unfortunately, the darts on her dress are too pronounced and quite distracting. A shame since the rest of the dress is lovely,” a member of the fashion police wrote on the Royal Hats blog. “I think she can do better than this! Ill fitting dress, and no connection to the hat and stripe on skirt,” another concurred.

Princess Eugenie of York channeled an early ’60s pre-O, Jackie Kennedy, when she donned a nifty Fiona Graham pillbox hat and powder blue bespoke Gainsborough boucle shift dress for the Windsor wedding of Prince Harry, Duke of Sussex, and Meghan, Duchess of Sussex in May 2018. The royal finished the look with a pair of $1,000 Valentino Garavani “Rockstud” 100 T-bar leather heels and a $1,800 M2Malletier Amor Fati beige colored leather top-handle purse.

The pillbox hat stems back centuries but was revived by Kennedy, who championed the headwear during her time as FLOTUS. However, sadly, Eugenie failed to live up to the style icon and appeared more provincial than presidential.

“Eugenie makes the Kardashians look classy,” a Daily Mail reader sniffed in the comments section of a post about matching wall paint to the color of the royal’s millinery masterpieces. Yes, really. “Those hats are absolutely so sad. No street cred there! Lol,” another wrote.

Princess Eugenie of York and her sister Princess Beatrice of York made headlines all over the world, for all the wrong reasons, in April 2011. The siblings were roundly ridiculed for the choice of headwear they wore to watch William, Prince of Wales, walk down the aisle with Catherine, Princess of Wales: scene-stealing, over-the-top, and fantastical fascinators created by celebrated British milliner Philip Treacy.

The mad hatters immediately made history for donning two of the craziest royal wedding headpieces ever. It was something they took to heart, but ultimately laughed about and turned into charity gold. 

“When everyone else was saying you look ridiculous, you have to have a sense of humour about that, and I was able to raise awareness about some incredible issues by using humour,” Beatrice told Vogue in November 2017, sharing that they raised £75,000 ($101,000) for UNICEF and Children in Crisis after auctioning the hats on eBay.

The outfit Princess Eugenie of York wore to a Service of Thanksgiving at London’s St Paul’s Cathedral in June 2012, as part of Queen Elizabeth II’s ongoing Diamond Jubilee celebrations, was likely a massive hit with any unlucky children forced to attend the stuffy service — thanks to its resemblance to every toddler’s favorite cartoon Tyrannosaurus rex, Barney the Dinosaur.

However, the purple, crumpled, quilted, and sateen dress was less than flattering and far from a style hit.

Daily Mail columnist Liz Jones branded Eugenie’s attire “purple but patchy” in a September 2018 op-ed. “The cowl neck is all wrong for her bust and the Suzannah dress hideously creased,” she opined, awarding points though for her “spot on” jaunty lilac Stephen Jones hat.

Princess Eugenie of York spiced up her style when she attended The Anti Slavery Collective’s Winter Gala at London’s Battersea Arts Centre in November 2023. Her sultry Peter Pilotto & Christopher de Vos satin floor-length gown was a dramatic change from the usual boxy, tweedy, and outdated garb Eugenie so often favors.

However, the thigh-high side split, topped with four pearl-embellished buttons and decorative gold insignia, made for an overall look that was more reality TV than royal red carpet.

Daily Mail commenters were predictably brutal. “Money does not buy class,” one sniped. “[Eugenie and Princess Beatrice of York] have the unfortunate looks of both their parents and the most abysmal taste in clothes,” another opined.

Princess Eugenie of York appeared fit to hit the grid when she attended the Vogue World: London extravaganza in September 2023. She had given birth to her second son, Ernest George Ronnie Brooksbank, at the end of May and was finally free of the maternity wear.

But Eugenie’s Fendi silk gown, designed by Kim Jones, positively swamped her baby bump-free figure, and its billowing shoulders and bright emerald-green hue left her looking more like a Seattle Seahawks linebacker than British royal reveler.

Her choice of attire rendered many speechless. However, you can always rely on the X fashion police to rustle up some opinions. “Ugly dress. Not flattering at all,” one cop wrote. “I agree. Looks like somebody wound a length of material around her,” a second concurred. “She’s as bad a Meghan, and that dress looks awful on her she doesn’t have dress sense at all,” a third opined, dragging Meghan, Duchess of Sussex, into the frightful fashion affray.

The annual invite-only Serpentine Gallery Summer Party charity fundraiser in Kensington Gardens, London, attracts all of the entertainment and fashion world’s finest, in addition to the inevitable socialites and royals that wouldn’t miss the unwrapping of a candy bar if there were photographers in attendance.

June 2018’s event was no exception. Chanel sponsored the elite extravaganza, and party guests hobnobbed in the French fashion house’s very best finery in addition to other high-end designer duds.

Then there was Princess Eugenie of York. She was clad in an ARITZIA asymmetric graphic floral print one-shoulder dress over black pants paired with open-front black shoe boots. It made for a look that was — interesting? Maybe tasteless? Take your pick.

Princess Eugenie pulled out all of the tasteless style stops when she attended the Firm’s annual Easter Sunday service at St George’s Chapel, Windsor Castle, in April 2018. 

The royal’s brightly colored paint-splattered-style puffy skirt and neon pink pillbox perched on her head ensured she stood out from the crowd as she marched into the church alongside her smartly suited-and-booted then-fiancé, Jack Brooksbank.

It was undoubtedly a nontraditional choice of attire for such a traditional event. And, design detractors didn’t fail to notice the right royal disaster. “The York girls need a decent stylist … it is very rare for them to get their whole outfit ‘right,'” one commenter wrote on RoyalHats.net.

Princess Eugenie reached deep into her closet for some glam garb to celebrate what would have been the late great Freddie Mercury’s 65th birthday in September 2011. Unfortunately, what she retrieved and subsequently wore to the soiree at London’s swanky Savoy Hotel left much to be desired.

Eugenie was attending the annual “Freddie For A Day” charity gala that benefits the Mercury Phoenix Trust, a non-profit set up in the Queen singer’s name that helps fund the global battle against HIV/AIDS. According to its website, celebrants are encouraged to “dress up Freddie style to remember the legend on his birthday and during other times of the year.”

Sadly, Eugenie massively missed the mark, as it’s unlikely the flamboyant entertainer would have been seen dead in her ill-fitting, lopsided, red chiffon dress and raggedy rhinestone shoulder wrap. Still, Eugenie did don a big bushy Mercury moustache later in the night, so there’s that at least.