Over the years, Princess Beatatrice and Princess Eugenei have worn some truly memorable outfits. Some for the right reasons, and some for reasons they probably wish people would forget. From viral fascinators and bold color combinations to outfits that sparked endless headlines and internet jokes, the York sisters have given royal fashion watchers plenty to talk about.
So today I’m counting down the 10 worst dresses worn by Princess Beatatrice and Princess Eugenie. Princess Eugenie. Kicking off the list is a look that perfectly captures some of the most questionable fashion trends of the late 2000s. When Princess Eugenie attended the premiere of The Young Victoria in London alongside Princess Beatatrice and Sarah Ferguson, she certainly made a statement, but not necessarily for the right reasons.
For the premiere of The Young Victoria, Eugenie opted for a short cream colored cocktail dress featuring a heavily embellished sheer neckline covered in intricate beading and decorative detailing. While the dress was undeniably youthful, I think the combination of the ornate neckline and loose flowing silhouette made the overall look feel somewhat unfinished rather than polished.
She paired the dress with black peep toe heels, creating a stark contrast against the soft light colored fabric. Unfortunately, the darker footwear felt quite heavy compared to the delicate nature of the dress. Her styling also reflected the trends of the late 2000s. The short auburn hairstyle, dramatic dark eye makeup, and heavily lined eyes gave the look a youthful edge, but together they created a much harsher effect than the romantic dress seemed to call for.
Looking back, I don’t think any individual element is necessarily a disaster. The issue is that the dress, shoes, and beauty styling never fully come together as one cohesive look. Instead of appearing elegant and refined for a major film premiere, the outfit feels slightly mismatched, which is why it earns a place on this list. Princess Beatatrice.
Attending the wedding of Prince Filippos of Greece and Nina Flor in 2021. Princess Beatatrice chose a Gucci gown she had previously worn 3 years earlier. I always appreciate royal outfit recycling, and I think rewearing beautiful pieces is something more royals should do. However, for me, the dress itself is where the problems begin.
The gown combined several very different design ideas into one look. The top featured an ivory wrap style bodice with long bishop sleeves, while the bottom transformed into a dramatic black A-line skirt. Individually, both elements are elegant, but together they create a sharp contrast that can feel a little disconnected.
Then there’s the embellishment. The neckline and waistline were heavily decorated with sparkling rose gold crystals, which already added plenty of visual interest. But the real focal point was the enormous pink sequined bow placed directly at the waist. Honestly, this is the detail that throws the entire look off balance for me.
The bow is so large and attention-grabbing that it immediately becomes the only thing your eye focuses on. Instead of complimenting the gown, it dominates it. Combined with the crystal embellishments, the dress starts to feel like several separate outfits merged into one design. To her credit, Beatatrice styled the look beautifully.
Her soft half up hairstyle and polished curls added romance, while the simple black clutch ensured there weren’t any additional distractions competing with the gown. Princess [snorts] Beatatrice. Next up is a look that sparked plenty of discussion when Princess Beatatrice arrived at the VNA summer party in 2017. While the dress came from one of the most popular royal approved brands of the time, this is a great example of how even a fashionable designer piece doesn’t always translate into a successful red carpet moment.
For the event, Beatatrice chose a self-portrait midi dress crafted from geometric gapure lace, mesh panels, and crepe fabric. The design featured a high Victorian inspired neckline, tiered ruffles, and an A-line skirt, meaning there was already a lot happening visually before you even got to the styling.
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What stands out to me is that the dress seemed caught between several different aesthetics at once. It combined romantic lace, Victorian details, sheer panels, ruffles, and modern cutouts all in one design, making the overall look feel a little overcrowded. The biggest issue, however, came from the transparency of the fabric.
Bright camera flashes made the under layer and shapewear much more visible than intended. As a result, much of the conversation surrounding the outfit focused on the sheer effect rather than the dress itself. Beatatrice kept the accessories minimal with a dark box clutch and very little jewelry, which was probably the right decision given how detailed the dress already was.
She also paired it with black platform heels while her auburn hair was styled in soft side parted waves with naturallook makeup. Princess Beatatrice. If there’s one thing Princess Beatatrice has never been afraid of, it’s making a fashion statement. Unfortunately, this 2008 wedding guest look is a perfect example of how a bold statement can quickly become a little too much.
Attending her cousin Peter Phillips’s wedding at St. George’s Chapel, Beatatrice arrived in an outfit that seemed determined to grab attention from every possible angle. The centerpiece was a Philip Tracy fascinator covered in realistic multicolored butterflies that appeared to be flying around her head. It was certainly whimsical, but for me, it crossed the line from playful into costume territory.
The problem wasn’t just the hat, it was what she paired it with. Beatatrice chose a tiered satin dress featuring multiple jewel toned bands that created a rainbow effect throughout the skirt. While the colors were intended to complement the butterflies, the combination of a rainbow dress and a butterfly covered headpiece made the overall look feel incredibly busy.
Instead of one standout element, there were several competing for attention at the same time. I can appreciate the creativity behind the outfit, but royal wedding fashion usually works best when there’s some balance. However, even the understated accessories weren’t enough to bring harmony to the overall look. Her auburn hair was styled in soft curls, and her makeup remained fresh and natural, which was probably the smartest styling decision of the entire ensemble.
Princess Eugenie. For the Serpentine Gallery Summer Party in 2017, Princess Eugenie stepped out in a fitted kneelength dress covered in an explosion of bold colors and abstract patterns. The design featured swirling motifs, floral elements, and contrasting shades of red, blue, yellow, gold, black, and white, all competing for attention at once.
My biggest issue with this look is that the print completely overwhelms the silhouette. The dress itself has a fairly simple shape, but the intense pattern makes it difficult for the eye to focus anywhere. Instead of highlighting Eugene, the first thing you notice is the fabric. The thin black belt attempts to add some structure to the outfit, but it gets somewhat lost against the busy design.
To her credit, Ujane kept the rest of the styling relatively restrained. Her jewelry was minimal and her sleek shoulderlength hairstyle helped prevent the outfit from becoming even busier. Looking back, I think this is a perfect example of a dress wearing the person rather than the person wearing the dress. The colorful print certainly made a statement, but for me, it felt more distracting than stylish, which is why it earns a spot on this list.
Princess Eugenie. For the Commonwealth Youth Forum reception in London, Eugenie chose a high street whistles dress featuring a colorful floral print set against a dark background. The dress had long sleeves, a high neckline, and an above knee hemline, giving it a much more casual feel than what people typically expect from a royal attending an official Commonwealth event.
The dress itself wasn’t necessarily the problem. For me, the issue was the overall styling. Pairing the shorter hemline with slouchy knee high suede boots created a look that felt more weekend brunch than formal diplomatic reception. A lot of the discussion surrounding this outfit also centered on how far it strayed from traditional royal dressing conventions.
Eujenei skipped tights entirely and embraced bare legs, which was considered an unusually relaxed choice for an official engagement at the time. While I appreciate that she was trying to bring a younger and more modern approach to royal fashion, the combination of the floral mini dress and casual boots felt a little too informal for the occasion.
The look seemed caught somewhere between a daytime social event and an official royal appearance. Princess Beatatrice. This entry might be one of the most controversial on the list because I know plenty of people actually loved this look. But when I look back at Princess Beatatric’s appearance at the 2018 MetGala, I can also understand why it divided fashion critics.
For fashion’s biggest night, Beatatrice chose a custom Alberta Ferretti gown in a striking royal purple shade. The dress featured layers of silk chiffon, mesh, and tulle along with a high neckline, flowing sleeves, and a floorlength Grecian inspired silhouette. On paper, it sounds like the perfect fit for the heavenly bodies theme.
However, for me, the outfit suffered from trying to do too many things at once. The dramatic purple color was already a major statement. >> [music] >> Then came the billowing sleeves, the jeweled embroidery on the collar and cuffs, the flowing chiffon layers, and finally the ornate crown-like headband. Instead of one clear focal point, the eye didn’t really know where to land.
The headpiece was probably the most talked about element of the entire look. While many fashion commentators praised it and credited it with helping popularize the oversized headband trend that followed, I personally think it competed with the gown rather than complimenting it. Combined with the embellished collar, it made the upper half of the outfit feel especially crowded.
Beatrice completed the ensemble with gold strappy heels and a simple black clutch, while her hair was styled in soft halfup waves, and her makeup remained natural and understated. What makes this look land on my worst dressed list isn’t that it’s unattractive. Far from it. It’s that the final result felt more costumelike than fashionforward.
For an event that celebrates bold creativity, I appreciate the ambition. But for me, the combination of the rich purple color, ornate embellishments, dramatic sleeves, and crown headband created a look that felt a little too theatrical and overwhelming rather than effortlessly regal. Princess Eugenie. At first glance, there’s nothing obviously outrageous about the outfit.
In fact, compared to some of Eugene’s more experimental fashion moments, this Diamond Jubilee look is actually quite polished. But for me, that’s also where the problem begins. For Queen Elizabeth II’s Diamond Jubilee celebrations in 2012, Eugene wore a bespoke Susanna London shift dress in a bold plum purple shade.
The structured silk satin design featured clean lines, a boat neckline, and subtle cap sleeves, creating a very traditional silhouette. The issue is that the outfit almost feels too safe and a little dated. While the rich purple color certainly made a statement, the combination of the structured shift dress and matching fascinator gave the look a somewhat matronly feel, especially for a young royal in her early 20s.
The coordinating Steven Jones fascinator continued the monochromatic theme featuring floral and quill embellishments. While beautifully crafted, I think the matching hat and dress created a look that felt overly coordinated rather than modern or fresh. She completed the ensemble with nude patent pumps and a neutral Lauro Piana clutch, choices that were elegant but didn’t really add any excitement or contrast to the outfit.
Her hair and makeup were soft and polished with loose curls and natural makeup providing a youthful touch. In fact, I would say the beauty styling helped prevent the outfit from feeling even more formal than it already did. Princess Eugenie and Beatatrice. No list of Princess Beatatrice and Princess Eugenie’s most criticized fashion moments would be complete without the royal wedding that launched a thousand memes.
When the sisters arrived at the 2011 wedding of Prince William and Kate Middleton, they instantly became two of the most talked about guests. Not because of their outfits elegance, but because of the sheer amount of attention their headpieces generated. Let’s start with Princess Beatatrice, whose outfit was almost completely overshadowed by what was sitting on her head.
She wore a fawn colored Valentino out couture coat and matching dress creating a soft monochromatic look that on its own was actually fairly sophisticated and appropriate for a royal wedding. Unfortunately, almost nobody was talking about the dress. Instead, all eyes were on the now infamous Philip Tricy Fascinator.
The pale pink creation featured a giant looping oval structure topped with a bow, leading the internet to compare it to everything from a pretzel to an octopus. Within hours, the hat had become one of the biggest viral fashion stories of the decade. To her credit, Beatatrice handled the situation gracefully and later auctioned the hat for charity, raising more than $130,000 for UNICEF and children in crisis.
If Beatric’s look was dominated by the hat, Eugenie’s outfit had the opposite problem. There was almost too much happening everywhere. She chose a highly structured Viven Westwood ensemble featuring a bright aqua blue bodice, a plunging sweetheart neckline, a green and white patterned wrap detail, and a royal blue skirt.
Individually, many of these elements could have worked, but together they created a color combination that felt chaotic rather than cohesive. Then came the Philip Tracy headpiece. The electric blue skull cap was decorated with dramatic beige feathers and purple flowers bursting outward from the side. Much like Beatatric’s Fascinator, it became one of the most discussed accessories of the entire wedding.
Adding metallic gold, Jimmy Chew pumps, and a Union Jack ring only made the outfit feel even busier. More than a decade later, people still remember these looks instantly. But unfortunately, they’re remembered more for the hats than for being style successes. Some of these looks became internet sensations.
Some sparked debate among royal fashion fans and others have simply become unforgettable moments in royal style history. Now I want to hear from you. Which outfit do you think deserved the number one spot? And was there a Beatrice or Eugenie fashion fail that I missed? Let me know in the comments below. If you enjoyed this video, don’t forget to like, subscribe, and turn on notifications for more royal fashion rankings, style history, and iconic royal moments.
