Kate Middleton Fashion Mishaps That Stunned Royal Fans

If there's one thing we know about Kate Middleton, it's that she's super sophisticated and super stylish. The Princess of Wales' style transformation over the years really has been something to behold, as we've seen her go from shy student to a stunning working royal and mother of four. For more than a decade, she's wowed us with her effortlessly elegant looks at both public events and casual outings; surely no easy feat when the world's eyes are on you pretty much 24/7.

But while we know Middleton has certainly rocked some sensational outfits, she has endured quite a few awkward fashion mishaps too. And because they're so rare, that actually makes them all the more shocking to see. From gusts of wind, to wrinkled ensembles, to just downright frumpy looks, we think maybe this gorgeous royal could do with just a quick refresher of our very best tips to help avoid fashion mishaps.

Stiletto heel + grate = awkward moment. And Kate Middleton found that out the hard way a couple of times. The royal has fallen victim to the heel stuck in a grate snafu at least twice in public, with the first happening back in March 2013. When the now Princess of Wales attended a St. Patrick's Day parade in England, she had to adjust herself after her black velvet shoe got wedged in the small gap. Luckily, Middleton managed to free herself, but we're guessing this was pretty awkward with all eyes on her.

The same thing then happened again in February 2018 when she wore a similar pair of black heels (these were slightly higher, though) while opening a treatment center in England. That time, Middleton was literally stopped in her tracks in her stylish court shoes while greeting well-wishers, including one person with an awkward royal history of his own. Middleton chatted with the Vice Lord Lieutenant of Essex, Jonathan Douglas-Hughes, who'd previously tripped while meeting the now Princess of Wales and her husband William, Prince of Wales. "I reminded her [about the fall]. My wife told her that she would ensure I didn't do it again. Then she caught her heel. [Middleton] said, 'Oh... do the same as you!'" he said after the event (via People), proving this royal knows how to poke a little fun at herself. Even after a literal fashion misstep.

We've all been there with a billowy dress and a gust of wind, but unfortunately for Kate Middleton, there are cameras nearby when it happens to her. In July 2011, Middleton had a dangerous moment while visiting Calgary, Canada, alongside Prince William. When the royals got off their plane, they were greeted with a rather unfortunate gust of wind that blew up Middleton's yellow dress. She almost flashed her rear end while she chatted with military personnel who were there to greet her, while snaps also showed the outfit blowing up at the front so much she had to hold it down using her clutch bag. Luckily, the working royal just managed to avoid exposing her undies to the world, but it was still considered an unfortunate mishap for a member of the royal family.

After that awkward moment, the designer of the dress, Jenny Packham, vowed she'd add extra weight to the bottom of any future dresses she might design for Middleton. "I had a little handwritten letter from a lady in Wisconsin passionately criticizing me for the primrose yellow shift dress I made for the duchess. She said didn't I know about putting weights around the bottom of a hem, so it can't blow up?" the fashion designer told The Standard. "Well, I didn't know it was going to be worn on a windy runway. But I did think maybe in future I will put in more weighting, just in case..."

Unfortunately, Kate Middleton's visit to Canada wasn't the only time she had a fashion accident involving a sudden gust of wind. She almost suffered another major wardrobe malfunction when her polka dot dress blew up in a big way in May 2013. Making this one even more embarrassing? This dress gust actually happened at the wedding of her friends William van Cutsem and Rosie Ruck Keene in Oxfordshire, England. Super awks.

But she still wasn't safe from those pesky gusts even after that. In April 2016, she had yet another dress issue when she almost went full-on Marilyn Monroe. While on a royal tour in India, the wind lifted the skirt portion of her white Emilia Wickstead dress as she walked alongside her husband and leaned towards a monument. Luckily, Middleton managed to prevent the skirt from flying up so high it revealed all, but this was certainly one of her closest shaves when it came to accidentally flashing her undergarments to the world.

Now for a fashion mistake that didn't involve the elements; just a senior royal making an honest error. In March 2019, Kate Middleton showed off her high-fashion side by stepping out in a stunning purple Gucci blouse. She no doubt looked gorgeous in the designer number while in London to pay a visit to the Henry Fawcett Children's Centre, only, she was wearing the blouse the wrong way round. Oops. Over on Nordstrom, the product photos show the bow tied around the neck, just as Middleton wore it, but with the buttons all the way down. The royal opted to button it up at the front, with the bow covering up the buttons. We're guessing she has plenty of people around to help her button it at the back, so we have to believe this was a genuine faux pas for the star.

But it seemed like Middleton obviously didn't get the memo, even after she'd already worn it, because she went on to wear the blouse back-to-front once again. Double awkward. Middleton wore the blouse with the buttons at the front again the following year while starring in a video to promote Five Big Questions, a survey which focused on childhood development.

The Gucci blouse blunder wasn't the only time Kate Middleton appeared to confuse the direction of her garments. Again in 2019, she wore an off-the-shoulder cream dress by designer Barbara Casaola backwards while attending an Addiction Awareness Week Gala Dinner in London.Though the dress itself was gorgeous and elegant, it stunned royal fans because it looked as though she'd worn in back to front.

You see, she wore the zipper at the front with the metal tag sitting on her chest. And with most dresses having a zipper either at the side or at the back, that had many people believing she'd accidentally sported the sophisticated gown backwards. Many fans flooded to social media to point out the mishap, too as we're not exactly used to seeing royals with zippers on the front of their dresses rather than the back. However, some websites selling the dress did actually show it with the zipper at the front rather than the back, so we can probably forgive the royal for this potential mistake. But, to be fair, it's arguably not customary for royals to have such exposed zippers on their garments.

While attending the Wimbledon tennis tournament in July 2023, Kate Middleton hit the headlines for all the wrong reasons — because she handed out a trophy in an extremely wrinkled dress. The royal, whose garments are usually perfectly pressed and ironed, had sat for a while in the green Roland Mouret dress, so when it came time to hand a trophy to tennis pro Carlos Alcaraz after he beat Novak Djokovic it wasn't exactly looking its best. The number had crease lines all the way across her hips which, while we've all been there, just wasn't very, well, royal of her. And fans certainly noticed.

"I was surprised to see wrinkles. Her clothes are usually pristine," one person wrote on X, formerly known as Twitter. Another fan was a little more understanding though, but still shared their surprise over just how wrinkled her dress had gotten seemingly so quickly. "Love the Look but not a fan of Mouret as it will crease once you sit for long. But she sure can rock green," they wrote on the social media site. And they weren't wrong.

Just over a decade before her creased dress debacle, Kate Middleton caused a stir when she was visiting the Solomon Islands for a cultural celebration — but accidentally wore a dress by a designer from the Cook Islands. It's usually customary for the royals to choose outfits by a local designer for such occasions, which is why this dress choice hit a few headlines.

Kensington Palace issued a statement about the furor, claiming that Middleton and Prince William (who also wore an outfit that originated from the Cook Islands, several thousand miles away) both believed their outfits originated from the Solomon Islands when they put them on. "We saw they weren't the same design of the traditional clothes we were told would be gifted, so we checked with the Solomon Islands government to ensure the right ones were worn. We were reassured the clothes were correct, and so the Duke and Duchess wore them to the event," the statement read. "It was not learned until later in the evening that the clothes weren't from the islands." The statement also confirmed that the royal couple's intention was made clear to anyone who may have been offended by the choice. "It was understood that the Duke and Duchess intended to wear traditional Solomon Island clothes and this was appreciated. No offense was caused," the spokesperson added.

A green screen probably isn't the first thing you'd think when it comes to things Kate Middleton has being compared to, but that's exactly what happened in June 2023. The floor-length off the shoulder Solace London dress she opted for when she attended the Earthshot Prize awards was actually pretty stunning. In fact we think it was one of Middleton's best winter looks ever. The problem more came from the exact shade of green she was wearing, as it resulted in a whole and people getting very creative online. You see, the green hue was the exact color of a green screen, which is used in the arts world to create things like CGI backgrounds.

Many poked fun at the very distinct color and actually used photos of the Princess of Wales as a green screen to superimpose their own kooky designs on it. As TikToker @goodwill.hunter put it in a TikTok video, "[This is] what happens when your stylist doesn't understand internet meme culture & photoshopping." And, sadly, Middleton and her team learned the hard way. The dress had everything from pizza toppings to The Dress (remember that whole black/blue dress or gold/white dress drama?) added onto it. While we're guessing though Middleton probably saw the funny side of the whole thing, we'd say she probably won't be falling over herself to wear that exact shade again anytime soon.

Kate Middleton had some fashion watchers scratching their heads in April 2011 when she decided to wear a predominantly black outfit to a wedding. She and Prince William attended Harry Aubrey-Fletcher and Louise Stourton's big day, and she paired a Libelula velvet coat dress with a plunging sheer mesh top and black fascinator. There's no doubting she still looked chic, but the whole look was arguably a misstep for a spring wedding. And clearly a few people thought so. One person wrote on Instagram of the look, "Way too daring for a wedding." Daily Mail questioned if the outfit was the most appropriate the royal could come up with, while Today even declared, "Royal Scandal Alert." Yikes.

Although it arguably has become more socially acceptable for guests to wear black to western weddings, black hasn't traditionally been worn to such celebratory occasions. As wedding etiquette expert Elaine Swann explained to Brides, "In many instances, especially here in the United States, wearing black to a wedding has been seen as a fashion faux pas because typically the color black is associated with mourning." And the royals especially have taken that to heart, as black is part of their somewhat strict dress code after a member of the royal family passes away. So, overall, we're filing this one under a rare fashion misstep for the usually so stylish star. Especially when she must have had so many other options at her disposal.

We all (well, most of us, at least) probably have an embarrassing prom dress picture lurking somewhere in a photo album. Even Kate Middleton kinda of does. Well, at least the internet thinks so. In October 2018, the royal appeared at a Buckingham Palace state banquet wearing a dress that it's safe to say hasn't been hailed as one of her best. The gown, designed by Alexander McQueen was made of a shiny blue/silver fabric with a mermaid style bottom. And although Middleton can pull off pretty much anything, even she couldn't really save this gown (which even featured a rosette in the same material on the right side of her chest).

The star took some flack online over the rare misstep, with plenty sharing their opinions of it on social media. Some even compared the look to a throwback prom dress. "Sorry but [Kate Middleton] missed the mark this time in a big way. This dress was horrendous," one person tweeted. Another wrote, "My prom dress circa 1995." Yeah, we're guessing that wasn't exactly a compliment.

How could we talk about Kate Middleton's fashion mishaps without discussing one of her most iconic looks of all time? But iconic for all the wrong reasons. Of course, we're talking about that notorious sheer lace strapless dress she wore during her school days. The year was 2002, and Middleton was asked to walk the runway as part of a charity fashion show at St. Andrews University. The see-through black number featured a turquoise stripe at the top to cover her chest, but she had to pair it with black underwear to cover her modesty. The now senior royal even set the look off with pieces of string fixed into her hair. Actual string.

This dress, naturally, couldn't be further from the sophisticated looks we've seen Middleton in more recently, and is arguably one of her most talked about looks ever. But, luckily, she's proven she knows how to laugh off a fashion mistake. Even one as big as this. In 2013, she returned to her former school for an anniversary charity event and joked about how, erm, far from elegant the dress was. Speaking to a fellow attendee at the event, Middleton said (via Harper's Bazaar Australia), "I hope you weren't involved in the fashion show. You never know what you are going to be asked to wear!" The dress was actually auctioned off in 2011, and brought in £78,000 (that's around $61,000 today!).

Though Kate Middleton may rely more on her tried-and-tested classic style than bowing to every new fashion fad (somehow, we can't see her giving the mob wife trend a go), she clearly was a bit of a trend follower before she became a full-time royal. There are several paparazzi shots out there showing how Middleton used to dress before she started taking on royal duties, and they reveal she was a big fan of low-rise jeans.

In one candid snap of Middleton's pre-royal duties taken in 2005, she flashed a little midriff in a strappy white top with acid wash denim. While the look was very of the time, it's not exactly very royal or regal and definitely isn't something we'd expect to see her in today. She was even been spotted pre-royal duties pairing her low-rise denim with light colored UGG boots. Now that's something we haven't seen in a while! 

Kate Middleton is no stranger to some exposure, but we're guessing this isn't the kind the royal family's publicists are after. While attending the wedding of Lady Rose Windsor and George Gilman in July 2008 (she sure loves a wedding, doesn't she?) the star showed a little bit more than she bargained for. Snaps show Middleton walking with a friend outside The Queens Chapel in London and accidentally exposing the silk slip under her patterned blue dress. Something that's not exactly very royal.

We have to admit, she pulled it off like a pro and managed to smooth the outer part of her ensemble back down before the outer part of the dress rode up too high. But we can't help but feel like this was probably a bit of an embarrassing moment for the young Middleton as she was just starting to get used to a life associated with the royal family.

Another shoe-related fashion mishap from Kate Middleton. Except this time, it was less about grates and more about mud. Middleton realized she maybe didn't wear the best shoes while out and about for a mental health awareness event in England in November 2022. As she greeted fans, Middleton had to walk over a supper muddy patch of grass in her gorgeous brown stiletto heels. And, well, it looks pretty tough and messy. We're guessing her stilettos ended up needing a good clean after her appearance.

But while the choice to wear thin heels in the muddy British winter was probably a bit of an oversight on Middleton's (or more likely her stylist's) part, fans did praise her for doing all she could to meet her fans, even in the less than ideal fashion conditions. Caroline Cheetham, a local resident who turned out to show their support for the royal, told Yorkshire Live, "It was wonderful to see royal couple. Kate was an absolute star braving the muddy grass to greet people." Points for wearing elegant heels in the mud? 0. Points for making it work regardless? 100.

Many of Middleton's fashion mishaps have largely been down to things outside of her control, such gusts of wind or unfortunate creasing.   However, during a royal visit to Sweden in January 2018, Middleton made a mishap that was completely in her control. She wore a blue velvet dress that totally overwhelmed her pregnant body and didn't fit with the elegance of the event.

The Erdem gown had a high neck and velvet bands about her neck and middle, with trumpet sleeves. It's probably safe to say the majority of users on X were not fans of the design, which kind of went against her usual chic and minimal style. "Kate is in another Erdem dress made from furnishing fabric (and why the black shoes?)" one person questioned on the social media site. "I thought the first Erdem dress ghastly....now this! Yikes!!" another tweeted. No wonder she's clearly since returned to her signature style!