Princess Eugenie's Most Outdated Looks

Princess Eugenie is a member of the British royal family. She's the granddaughter of the late Queen Elizabeth II and the niece of King Charles III. As of 2024, the princess also stands 11th in line to the throne. As a member of such a prominent house, Eugenie's lifestyle has been of much interest to royal fans, so it's a given that her fashion choices at royal outings and events have been making news since the early aughts. 

Eugenie has gone through quite an impressive style transformation and is seen today as another fashionable member of the royal family. But it took her time to achieve the level of confidence and style prowess that she has today. For instance, from adolescence onward, she experienced a number of wardrobe mishaps. Some of Princess Eugenie's most inappropriate outfits even garnered criticism from the public. In those early years, she seemed to struggle to find her own fashion identity and often wore outdated styles that made her look much older than she was. 

Princess Eugenie and her sister Princess Beatrice were both heavily criticized for the ensembles they trotted out as guests for the wedding of William, Prince of Wales and Catherine, Princess of Wales. Royal weddings have a particular dress standard, which includes women wearing hats. However, the princesses wore a smaller headpiece style called a fascinator that completely missed the mark. Eugenie had a bright blue fascinator to match the color of her dress, topped high with feathers and an over-the-top flower. British etiquette expert William Hanson told Vanity Fair that while a hat is needed for a royal wedding, a fascinator doesn't have the same elegant effect. "A fascinator makes you more noticeable," he said. "You've got to have great confidence to wear a fascinator; it's much more 'Look at me.' But they are not as sophisticated. Amongst the absolute crème de la crème in British society, no one would wear a fascinator."

Eugenie might have gotten away with the poor choice of headpiece if the rest of the outfit had been more stylish. Unfortunately, her dress was terribly unfashionable and old-fashioned. It featured a strangely uneven hemline and stiff bodice with dated-looking sleeves complete with padded shoulders. The princesses faced public backlash for these outfits, which they later admitted hurt their feelings a lot. 

Over the years, Princess Eugenie seems to have struggled to find her style. While attending a garden party in 2016, for example, the princess once again tried and failed to hit the right fashion note. She wore a collared white shirt with a matching full skirt featuring a unique and colorful print. She matched her salmon headpiece to one of the colors from the skirt's print, and then finished the look with a black clutch bag and block heels with an ankle strap. It's likely she selected the unique print in an effort to make the conservative silhouette appear more modern; unfortunately, with the combination of the eye-catching hat and creative print, it looked busy rather than fashion-forward.

Speaking to Femail about Princesses Eugenie and Beatrice, stylist Helen Canning said, "The Princesses often just miss the mark in the style stakes, edging a little too far on the quirky side and not quite pulling it together." Canning then added, "To avoid any fashion fails, my advice would be to keep it simple and therefore more timeless and ageless. So go bold, Princesses, but stick to one statement piece — not more than two in one outfit."

In 2012, Princess Eugenie wore a questionable peplum dress to the Royal Ascot horse racing event. The teal dress featured a buttoned peplum bodice, sheer black sleeves with a leaf-like pattern, and a strangely bunched skirt. She accessorized the look with tasteful black pumps, a black pillbox hat with flowers, and a white and black clutch. Although it looks quite dated now, some elements of this look were more in vogue when she wore it. Specifically, the peplum style was quite trendy in the early 2010s. Peplum is a style of blouse, jacket, or dress, with a strip of fabric flouncing out at the waist to create the illusion of an hourglass shape. The look was considered stylish in the '80s and was briefly back in fashion in the early 2010s before going out of style once again shortly after. We also saw peplum tops make a comeback in 2023. 

The dress might have been a cute look for the year had it just featured the peplum. But the dark lace sleeves were an outmoded cover-up design, and the bustled skirt made the whole thing look too busy and dated. Like many of her outfits, it was poorly tailored, making the ensemble less modern. 

Princess Eugenie wore a silky purple dress to a Diamond Jubilee celebration in 2017. This could have been an excellent style moment, but due to a few fashion mistakes, she looked a bit frumpy and outdated for the special occasion. The simple cut of the dress was very classic and flattering but a bit archaic. "'The purple outfit feels very 1960s Pierre Cardin to me, once again aging the Princess," fashion expert Miranda Holder told The Daily Mail. Other elements like the paneling in the skirt, the dramatic cowl neckline, and the color added trendy elements, which only made it look more dated rather than timeless a few years later. The real failing in this purple get-up was that the bell-shaped skirt was not properly steamed and featured visible wrinkles. The bodice and sleeves also didn't appear to fit well and could have used more careful tailoring. 

Eugenie did, however, accessorize the outfit well. Her headpiece is a lighter purple than the dress, and she carried a nude clutch to match her heels. The slight variations in tone gave the ensemble a well-thought-out appearance without being too matchy. "She is almost there, but not quite," Holder said. 

A quick glance at Princess Eugenie's fashion history is like looking at a colorful array of ridiculous hats. Both her most beloved and most criticized looks tend to include a daring headpiece, and this affinity for hats started early in her fashion journey. For instance, back at the 2008 Royal Ascot, a yearly horse race attended by the royal family, Princess Eugenie arrived in a cream dress with silver embellishments, a blue blazer, and a matching fascinator decorated with flowers and attention-grabbing feathers. Extravagant headpieces are an expected accessory at the prestigious event — the royal family's best Ascot looks all feature fun and dramatic headpieces – but we still would have liked to have seen Eugenie finish the look with a more modern hat. "'The hat is the finishing touch, but makes the outfit far worse, being way too fussy and complicated. Once again, the look is dated and aging," fashion expert Miranda Holder told The Daily Mail. 

Along with the hat, the matching blazer didn't do Eugenie any favors. The dark blue color was slightly out of place at the summer event, where a lighter color would have felt more appropriate; the darker tone especially stood out because of how much it contrasted with her dress. Additionally, the stiff collar and structured shoulders of the jacket made it seem too stuffy to go with the flowy style of the dress that she wore underneath. "[It] is a very heavy look that completely overpowers the Princess," said Holder. 

While attending a garden party at Buckingham Palace in 2016, Princess Eugenie looked a bit out of style in an ill-fitting white blouse and floral skirt that was hemmed at mid-knee. If the top had been more well-fitted, it might have produced a chic and flattering effect, but the baggy silhouette made the outfit look out of style, and it had an aging effect on the young princess. 

Her bright blue feathered hat, which she wore at an uncomfortable angle that obscured her forehead, did little to modernize the look. It's clear the princess is a fan of unique headpieces, and she often uses them to make a fashion statement. However, in many cases, like this one, her choices detract from rather than elevate the look. "I can see what Princesses Eugenie and Beatrice try to do with their headwear and that is to liven up more mature outfits but it doesn't quite work and often looks accidental," stylist Helen Canning told Femail. "A splash of color in a less fussy headpiece would serve to complement their look and not overpower it, and positioning is key; keep it off your face and don't let it wear you."

Princess Eugenie experienced another fashion fail while attending the Royal Ascot in 2009. Her outdated attire featured a collarless purple top with three-quarter-length sleeves, a basic white pencil skirt, and a lime green fascinator, which she placed right at the front of her head. The loud purple and green colors made her instantly noticeable, but unfortunately, not in the best way. Eugenie's outfit was quite outdated for the special event where royals and guests attempt to put their most fashionable foot forward. The traditional cut of the top looked boxy, even with the white belt cinching her waist. And while the pencil skirt could have been a classic base, it just looked a bit boring paired with the dowdy top.

Another mark against the outfit was that she tied it together with nude pantyhose, of all things. Although members of the royal family often wear nude tights, they have an unfortunate aging effect that accentuate the less stylish elements of your outfit. Vanessa Friedman, fashion director of The New York Times, explained this phenomenon, saying, "For women of a certain age, [pantyhose] are simply a part of girding yourself for the world; for others, they are a symbol of old-fashioned female repression and outmoded gender rules." Seeing the nude tights on Eugenie at a summer event simply made her whole outfit more stuffy and passé.

The black and white look that Princess Eugenie wore to a day at the races in 2009 was a bit too matchy-matchy to be fashionable. She wore a cute, flowing black dress with white polka dots and a matching polka-dotted hat with a bunch of white flowers at the front. Polka dots typically have a whimsical and youthful look, but the overly matchy nature of the hat and dress canceled that out. Although the outfit's coordination clearly took some thought, it made the princess look dated beyond her years. Many women from older generations were raised with the idea that they had to match their accessories carefully to their outfits; because of this, that style has become old-fashioned over the years. 

Fashion stylist Tan France advised on how to accessorize in a more modern way, saying, "Matching accessories can read more conservative than fashion-forward. If you're not sure which colors go together, start by adding one colorful accessory to a base of neutrals. Then, use the color wheel to get new ideas for bold color combinations," (via MasterClass). Finishing the look with a fitted blazer and sheer pantyhose made it look more formal and less fresh. 

In 2017, Princess Eugenie attempted a daring color coordination when she donned a bright blue dress with a beaded belt and an orange hat. While many of the outfit elements might have contributed to a beautiful look in a different context, all paired together, the accessories and dress didn't quite work. Apart from the asymmetrical neckline, the dress featured a traditional style and silhouette. This matched the traditional feel of the simple nude pumps and slim headpiece. However, the waistband's trendy pattern interrupts the classic look in a jarring way. 

"The accessories are mismatched," fashion expert Miranda Holder told the Daily Mail, in reference to the bohemian belt. "This can be a good thing, but in this case it looks a little haphazard." Mismatching accessories or colors is typically a good idea, but in this instance, the style of her hat, shoes, and belt clashed. Holder also pointed out that the length and cut of the dress were ill-suited based on Eugenie's age and figure. "The cap sleeves [are] too severe and unflattering," she explained. "The on-the-knee skirt length is also a bit matronly." To make matters worse, the high placement of the belt, which sat directly under the bust, contributed to the outdated silhouette.

The printed dress worn by Princess Eugenie to the 2013 Epsom Derby event was pretty but outdated. Eugenie's unique outfit featured a notched boat neckline, fitted waist, and flared skirt. The mid-knee hem length and high neckline gave the frock a very modest appearance. This isn't a bad thing, but it can easily look stuffy or old-fashioned unless carefully styled. What's more, the neutral colors of the dress added to the conservative feel. Although the mix of pale colors was beautiful, Eugenie could have gone with a bright or pastel palette to stand out at the outdoor horse racing festival. Adding an appropriate pop of color with accessories might have made this ensemble a bit more trendy, but she instead finished with a neutral clutch and saucer-like hat that blended in with the plain tones of the dress. She also covered her legs with nude pantyhose, which added to the overall outdated appearance.

The upside about this fashion moment is that the neutral tones brightened Eugenie's skin tone and hair. Because of how they highlight her natural features, some of her best looks are in a more neutral palette. However, in this case, the style of the dress and bland accessories took away from her youthful countenance.

A 2013 photo of Princess Eugenie sporting a teal ensemble was captured over a decade ago, but due to poor styling, the princess appeared older than she does in some of her more recent snapshots. Eugenie wore this form-fitting outfit while attending a wedding in Alnwick. It featured a simple dress, jacquard-patterned moto jacket, matching teal clutch, purple fascinator, and black pumps. The biker jacket was likely intended to add some edge to the otherwise conservative look, but instead, it looked out of place. As stylist Miranda Holder told the Daily Mail, the jacket's pattern looked similar to curtain fabric, which only serves to make the outfit feel more outdated. "It is clear that at this time, Eugenie hadn't really 'found herself' when it comes to fashion. None of her bubbly personality shone through with this look, which feels far too formal and constrained," Holder commented. The stylist also compared the 2013 outfit to a similar ensemble from 2019 and, despite the six-year difference, she said, "Although this is the earlier photograph, the look is actually making her look older!"

Over time, royal watchers can agree that the princess has found her fashion footing. The subtly sexy wedding guest style Eugenie showed us in 2024 is a clear example of this evolution, as it did a much better job at showing off her best features while looking both chic and elegant.