Princess Eugenie's Worst Outfits We'll Never Forget

Even though Princess Eugenie is a royal by birth — her father is Prince Andrew, the Duke of York — she's had a very awkward transition into becoming a woman of style. In fact, the poor princess has been beleaguered by fashion mishaps and flops for decades. From wearing inappropriate outfits to choosing strange patterns, her wardrobe has perplexed the nations. Additionally, Eugenie has an archive of makeup mistakes, so that has been yet another problem area for the royal. 

She's often photographed out with her sister, Princess Beatrice, and although they are close in age, there are striking differences in Beatrice and Eugenie's styles. Beatrice is often drawn to bolder prints while, as she's grown older, Eugenie goes for solid colors and less statement pieces. In fact, Eugenie has come a long way and, as a contemporary princess, she has come to understand what looks good on her. There's no denying that Eugenie has had a stunning style transformation in recent years, culminating in what was one of the most beautiful royal weddings, when she married Jack Brooksbank in October 2018. Her wedding dress was perfection, designed by Peter Pilotto and Christopher De Vos, and she looked absolutely stunning. Nevertheless, it is impossible to forget her biggest sartorial missteps.

In June 2008, Princess Eugenie attended the Royal Ascot in an outfit that would become a fashion blunder that would follow her around for decades. The Royal Ascot, which is made up of one week of horse racing at the Ascot Racecourse, got its resplendent title because it was traditionally attended by the king and queen and other members of the royal family, including Eugenie. Tradition dictates that guests wear their racecourse finest, which includes notable headwear or fascinators. While this can be a fun opportunity to exhibit something daring, Eugenie's ensemble of choice at the time was all wrong. 

Her fascinator, designed by haute couture milliner Philip Treacy, featured a beret-style base with vertical power, thanks to towering flowers and feathers, while her matching blazer featured ruffles along the shoulder seams. She paired this with a beaded white dress, which featured a high neckline and complex texturing along the skirt, and matching white gloves. The ruffles on the blazer were far too busy in combination with the elaborate detailing on the dress. On top of that, the textures and styles of the jacket and dress didn't complement each other. Instead, the outfit looked busy and aged the young princess.

The flashy fascinator served as the final death blow to this outrageous outfit, with a dizzying combination of textures. If Eugenie wanted to wear such a complicated headpiece, she would have been better off ditching the blazer and opting for a simple, tonal dress. 

Princess Eugenie attended the premiere of "Young Victoria" in March 2009 at Leicester Square, London, along with her mother, Sarah Ferguson, Duchess of York, and her sister, Princess Beatrice. For the occasion, Eugenie wore a short, cream colored silk dress with sheer, geometric detailing along the shoulders and chest and black heels. The outfit is a prime example of some of the sartorial mistakes that Eugenie made when she was younger. The length of the dress was too short for her, making her look childish. Plus, the front panel of the dress adds too much volume to her upper body and midsection, failing to accentuate her figure. Meanwhile, the strappy black heels are too busy to complement the already notable neckline of her dress. The outfit feels a bit slapdash, as if she randomly pulled the look together at the last minute. 

Like her sister, Beatrice has sported many outdated looks, which she demonstrated at this premiere. According to stylist Charlie Anderson for the Daily Mail, these poor fashion choices were a result of both sisters taking fashion cues from their mother. No diss to the duchess, but it didn't benefit either Eugenie or Beatrice to be dressing older than their ages.

Ah, the infamous wedding outfits. Both Princess Eugenie and Princess Beatrice got absolutely roasted online for their nuptial wardrobe choices on Prince William and Princess Catherine's wedding on April 29, 2011. The outfits were such catastrophes that they were among the biggest mishaps at William and Catherine's wedding.

Eugenie chose a blue skirt suit by Vivienne Westwood that featured a tucked hem. Instead of making the outfit more interesting, the tucked hem made the skirt portion look poorly tailored. Her jacket featured a fitted blue and green floral design with bows cascading down the front. She paired the look with gold platform pumps and, to top it off, Eugenie wore a blue fascinator by Philip Treacy. The extravagant headpiece featured large burgundy flowers and beige feathers that made the whole getup look like a costume rather than regal, royal attire. 

Royal fashion expert and celeb stylist Miranda Holder spoke to the Daily Mail about Eugenie's wedding guest look, saying, "The shoes didn't really go with the rest of the outfit and felt like a last minute addition, the skirt and corset top were overdone and felt extremely dated, the hat might have been [okay] with a totally different look, but the overall effect of this combination is far from flattering." This look has gone down in Eugenie's history as one of her worst looks ever. 

When attending the 2012 Service of Thanksgiving for the Queen's Diamond Jubilee, celebrating the 60th anniversary of Queen Elizabeth II's reign, Princess Eugenie wore an unflattering purple dress. Unfortunately, the material of the dress wrinkled horribly, and she emerged from St. Paul's Cathedral with creases all over. In a touching way, though, it reminded us of the late Princess Diana, who walked up the steps of St. Paul's Cathedral in a shockingly wrinkled wedding dress. In fact, it was one of the reasons Diana's wedding dress designer was so upset on her big day. The silk gown had completely crumpled, so we have some compassion for the state of Eugenie's dress. However, this wrinkling problem is one of the reasons royal women tend to avoid certain fabrics, like silk and linen. The goal is for the members of the royal family to look as polished as possible. 

But the wrinkling was just the beginning. While cowl neck of Eugenie's dress was fine, the garment cinched around her waist and then plumed out into a stiff balloon shape. The volume of which didn't enhance her silhouette. She wore a purple headpiece by Stephen Jones, and while it was more understated than many fascinators she's worn, its dusty lilac tone was not a good fit with the deeper purple dress.

Throughout her 20s, when she'd ideally be creating a style that suits a young, innovative royal, Princess Eugenie was frequently caught dressing in looks that were several decades too mature for her. This happened in 2013 when she attended a celebration for the anniversary of Queen Elizabeth II's coronation. Eugenie wore a teal skirt suit. With the hem of both the skirt and blazer, the outfit featured too many vertical lines to be visually appealing and instead looked choppy on the young princess. The blazer featured black zippers and hardware, which was ironically too modern for the brocade fabric of the jacket itself. The shape of the jacket wasn't flattering either. "The wide lapels on the jacket made her bust look larger and the boxiness of the dress underneath it has a squaring off effect, which adds to the frumpiness," Miranda Holder, celeb stylist and royal fashion expert, told the Daily Mail of this particular look. "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," the expert added.

On top of that, her fascinator was quite a sight — and not in a good way. Eugenie has often struggled with fascinators, and this was one such case. It looked strangely small on her head and the purple hue made no sense with the rest of her outfit. In fact, it would've been a better fit with her 2012 Service of Thanksgiving dress.

In 2014, Princess Eugenie attended the Royal Ascot yet again and, yet again, she made a fashion miss. She wore a short white skirt with a beige wrap jacket and nude heels with black ankle straps. This outfit was a clash of casual and formal pieces. Her belted jacket looked far too relaxed when paired with her skirt, heels, and fascinator. The point of the Royal Ascot is to come out dressed to the nines, but Eugenie looked drab in the boring outfit. In particular, the jacket had the vibes of a cropped housecoat more than a formal piece of outerwear. There were also too many colors happening at once, making the ensemble lack cohesion.

The fascinator on this day was a particular disappointment. It was far too small and ended up looking comical on the young princess, rather than elegant. Fascinators look best with formalwear, and Eugenie's outfit looked too casual to complement such a statement accessory. The outfit also failed because of the cluttered effect of the straps on her shoes in combination with her belt and the filigree of her headpiece; there were simply too many dangling parts. 

There's a real art when it comes to dressing for one's particular body type, and for most of us, this can take years to master. It is no different for Princess Eugenie. In 2016, at the annual Not Forgotten Association Garden Party at Buckingham Palace, she arrived with her father, Prince Andrew, and her sister, Princess Beatrice. Eugenie wore a sleeveless blouse with a blue and white floral skirt. As seemed to be Eugenie's ongoing problem at the time, the outfit aged her and didn't suit someone so young. 

To make matters worse, her top was billowy and ill-fitting. This would have worked if her skirt had been fitted, but because she wore an A-line skirt, which inherently has ample fabric, the loose blouse made the whole outfit too roomy for her. While the outfit was too big, Eugenie's Gina Foster hat completely flattened her head. Of the fascinators both sisters sported, stylist Helen Canning told the Daily Mail, "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."

It is also quite rare to see royal women wearing sleeveless outfits at events. While sleeveless outfits don't go against royal protocol, there is a strong emphasis on modesty and appearing professional. This is why you will rarely see members of the royal family sporting sleeveless shirts or dresses at public events. While Eugenie doesn't often wear this type of top, it was unusual to see her in something that comes close to crossing the line in the royal dress code. The same goes for necklines, and while Eugenie's wasn't shockingly low on this occasion, it was notably deeper than her sister's.   

Two days before wearing the sleeveless blouse and blue and white skirt, Princess Eugenie attended the queen's Garden Party, wearing a white, printed skirt by Alice + Olivia x Donald Robertson and a long sleeve white blouse also by Alice + Olivia. She wore black and white heels by Kurt Geiger, as well as a red fascinator by Sarah Cant.

Firstly, the skirt wasn't a great choice. The length of it gave an aging effect to the princess. The skirt wasn't knee length, but it wasn't quite midi-length, either, and it looked bulky. Add to this a voluminous, fully covered blouse and the final effect was simply too much fabric. On top of this, Eugenie's shoes featured ankle straps which can be notoriously unflattering. The strap breaks up the visual length of the leg, making one's legs appear shorter and thicker than they really are, and this was the case with Eugenie's black and white heels at this event. 

Stylist Helen Canning told the Daily Mail that Eugenie often struggled with getting her outfit quite right, largely because of the pressure of dressing appropriately. "While it can't be easy choosing an outfit as young Royals who want to look current, but also appropriate for royal engagements, it is possible to find looks which tick both boxes," she said. The Queen's Garden Party in 2016 was one such occasion where Eugenie tried to satisfy royal requirements, but didn't look youthful or fashion-forward. While she went for a more daring look for the next garden party, it unfortunately didn't help.

Princess Eugenie doesn't often cause an uproar by what she wears. In fact, the longstanding complaint against her fashion taste is that she dresses too old for her age, so a little injection of youthful recklessness would be most welcome. However, in 2018, Eugenie arrived at the Commonwealth Youth Forum wearing a black mini dress with knee high black boots. The dress was notably shorter than what she typically wears, and the internet got itself into a little tizzy.

In one moment at the event, Eugenie walked up a flight of stairs, and the hem of her dress was that much more evident. Simultaneously, Meghan Markle wore a sleeveless Altuzarra dress to the Commonwealth Youth Forum, which drew even more criticism than Eugenie's ensemble.

"I like Eugenie – I really do, but with all the talk of Meghan's outfit not being appropriate at the commonwealth event today, is anybody going to comment on the inappropriateness here???!" one person tweeted on X. This outfit also served as further proof of Eugenie's struggle to find the right balance, and that her fashion sense can be off. In this rare instance, rather than wearing something aging, her dress was too short, making royal watchers uncomfortable. 

If people are getting into arguments online about an outfit, it is probably not a great look. Princess Eugenie's 2024 Royal Ascot fit had people divided. On day one of the event, she arrived in a mint green "Mallery" dress by Diane von Furstenberg. Once again, the dress was sleeveless. Eugenie also wore a large, flat headpiece called the Siniang hat by Emily London Headwear, and paired it with a large flower pinned in her hair. She polished off the look with nude Aquazzura heels. 

The Duke and Duchess of Gloucester chatting with Princess Eugenie and Mr Jack Brooksbank at Royal Ascot Day 1. Love these family moments! ❤️💞❤️💞 pic.twitter.com/VEU2ac0t13

— Rodrigo (@The_QVDS) June 18, 2024

While some found Eugenie's look acceptable – Hello! magazine called her outfit a "summer dream" and praised the princess for her choice — the dress still aged her. "That's not the most flattering dress, but I've noticed Eugenie rarely gets it right," one person tweeted about this Royal Ascot look. Another wrote, "The dress is beautiful but not on her. She is someone that probably SHOULD wear prints. And I'm sure [von Furstenberg] could have hooked her up with something beautiful." A third X user posted, "She always dresses frumpy, surely there are beautiful dresses that would look way better!" In addition to the dress being a miss, her saucer-like fascinator also attracted criticism. Plus, she yet again wore a fabric that creases — and it did indeed crease, making her look less put together than she would've otherwise.