Here Are Kate Middleton's Most Controversial Looks To Date

With its gorgeous lace sleeves and nearly 9-foot-long embroidered train, Kate’s wedding dress was, for many, utter perfection. But there was one problem: it actually sparked a lawsuit. A designer called Christine Kendall took Alexander McQueen to court, maintaining the fashion house had used her original ideas without consent. By the looks of things, the case hasn’t been resolved.

We like to think Kate’s a party girl at heart — and this photo from 2008 seems to prove it. Check out the glow-stick bracelets! She was off to have fun at a roller disco at the time, and given that she was in her pre-duchess era, Kate could technically wear whatever she liked. Of course, the tabloids still had a thing or two to say about the outfit choice, with the Daily Mail labeling it “inelegant.”

Turns out Kate seemed to rather like flaunting her stunning figure back in the day. While taking part in a college fashion show fundraiser, she strutted her stuff in this see-through dress — if we can even call it that?! William is said to have attended this event, and seeing Kate in the outfit was apparently a game-changer for him. The duke’s friend Pat Duncan revealed to E! News back in 2011, “He was sitting [in the] front row, and his eyes were like stalks.”

The outfit Kate wore when she and William announced their engagement was perfect — just the right shade of blue to match the enormous sapphire gem in her ring. But this didn’t stop the dress from causing controversy. Oh, no. Predictably, lots of fans decided they’d like the same one. And the designer’s company crumbled under the high demand.

Sometimes, the wind can be a real “b” word. Kate knows this, having fallen foul to its tricks many a time. One of the most memorable such incidents took place back in 2011, when she and William visited those in the Air Force in North America. It looks like it was all she could do to keep everyone from seeing her knickers!

It’s got to be said: the Duchess of Cambridge loves a wedge. It’s a pity the Queen reportedly doesn’t feel the same, then, isn’t it? In the war, lots of people fashioned footwear from cork, as it wasn’t a rationed material. The monarch supposedly doesn’t like to look back on these times. Understandable, really.

Members of the royal family usually honor the countries they travel to with their outfit choices. It looked as though Kate tried to do this back in 2012, when she and William flew to the Solomon Islands. No doubt she was meant to be wearing a dress from this region. But it turns out that what she had on was actually made miles away in the Cook Islands. Whoops!

Kate always stands out at events, but this was especially true at the 2018 BAFTAs. Lots of people chose to dress in black to show their allegiance with the Time’s Up campaign, but the duchess stepped out in a floor-length dark-green number. Royals aren’t meant to engage in any politics, you see. Though some think the black belt was her discrete way of showing her support.

Just look at the Queen and Camilla in their muted-toned dresses. Yep, that’s them in the background! Your eye probably went straight to Kate in that bold get-up. And while the duchess looks stunning here, she did receive criticism for taking the focus off of her grandmother-in-law. It was the Queen’s Diamond Jubilee, after all.

What’s wrong with this outfit, we hear you ask? To us, the Alexander McQueen looks perfectly appropriate for a day out at the races. But to others, the lacy look was, er, a bit too racy. Yep, you read that right. Apparently, many felt the dress wasn’t long enough and that, because of the translucent material, Kate was showing too much skin. You can’t please everyone!

Kate looked positively radiant when she stepped out after giving birth to Charlotte — well, the same could be said for all of her post-birth appearances, come to think of it. But some people watching still found a reason to complain. Apparently, on this particular occasion, they thought the duchess looked “too perfect” for someone who’d had a baby just hours before.

Here are Kate and William sweetly play-fighting in the snow on their skiing vacation. While most of us were likely cooing over how happy the couple looked, PETA was quick to point out the duchess’ mittens had been made with real fur. Since then, the Queen has announced publicly that she’ll never dress in real fur again — but we don’t know if Kate will follow suit.

Word has it the Queen doesn’t like bright nail polish. If she’s going to paint her nails at all, it’ll be with a very subtle, light pink shade. Kate bucked this trend when she arrived at an evening event in London. Fans’ eyes were drawn straight to her toes, which were painted bright red. On the duchess, it looked gorgeous. But then again, Kate could make neon green look classy.

When Kate stepped out in this gown, made by London-based designer Erdem, it sparked a hot debate among fans. Some thought Kate was a vision in the heavily patterned dress, while others weren’t so keen. As one disgruntled fan wrote on Twitter, “Not my favorite floral dress on Kate today. Too old for her! A bit frumpy.”

Usually, royal ladies’ dresses must reach, or at least skim, their knees. So, when Kate emerged wearing a pair of shorts, fans were forced to do a double-take. To be fair to the duchess, she was taking part in a fundraiser sailing race. And she was competing against William, so she had to be fully prepared to get stuck in.

This dress is made for Kate. Just look how it perfectly hugs her gorgeous figure. More traditional fans may think the off-the-shoulder neckline to be a little too daring for a royal, but interestingly, that’s not why the outfit made the headlines. If you look closely, you’ll notice the zip is at the front. Was the dress on back to front? Well, no is the answer. Apparently, this is the correct way to wear it. But it still garnered lots of attention.

Kate has been known to step out with an item of clothing on back to front, though. Both times the duchess has been seen in this purple Gucci blouse, the buttons have been at the front. But they’re actually meant to run up the back. Kate clearly prefers it this way around. And if anyone can pull it off, it’s her!

Are skinny jeans appropriate for a royal? Kate Middleton seems to think so. She often throws on a pair for more laid-back outings, such as walks or engagements where she needs to get a little more active. The pant choice is probably on the cusp of how casual the royal can go, though. And you’ll notice how she’s usually in a darker, classier shade — and there are no rips in sight!

This striking red dress marked a turning point in the duchess’ Wimbledon fashion. Up until 2015, the outfits Kate wore to the tournament allowed her to blend in relatively well. Not this year. All eyes were on her in this attention-grabbing ensemble from high-end British brand L.K. Bennett. And check out that iconic leopard-print clutch. Too much for Wimbledon? Some likely thought so. We, on the other hand, think it’s stunning.

Kate wore this crisp, clean Alexander McQueen dress to Princess Charlotte’s christening back in 2015. Lots of fans loved the outfit, thinking it fit the occasion perfectly. But some fashionistas disagreed. Fashion expert Maureen Callahan commented, “It’s hard to imagine Alexander McQueen letting such a young, photogenic royal — the future queen, no less — look this deathly boring.”

It was in India that Kate had her Marilyn Monroe moment — unintentionally, we might add. Just as the duchess bent over to lay a wreath to commemorate soldiers who fought in World War I and the Anglo-Afghan War, an almighty gust of wind blew her skirt to the skies. It wasn’t ideal at such a solemn location. Maybe Kate should take a leaf out of the Queen’s book and get weights added to the hems of her dresses.

Later that day, William and Kate made their way to the Gandhi Smriti Museum. While there, Kate had to remove her footwear — not doing so would have been disrespectful. But, of course, eagle-eyed news outlets shot their glance straight to her feet. “Corns, clawed toes, bunions AND fallen arches,” was the title of the Daily Mail article that followed. And others were quick to point out that her toenails were au naturel.

Lots of people would kill to have legs like Kate, so why shouldn’t she show them off? Well, as a royal, it’s simply not the done thing. Every now and then, though, the duchess will push the boundary with how high that hemline can go. The Queen’s 90th birthday party was one of those times. Just look at the length of Princess Eugenie’s dress in comparison!

When Kate stepped onto the red carpet in this sexy number, website InStyle called it her “most revealing gown” yet. And they were probably right. The combination of the sheer bodice and that super-high slit grabbed the attention of royal fashion watchers everywhere. She looks gorgeous. Let’s hope this is a look she’ll recycle someday soon — that’s if she wasn’t given a talking to by the Queen, of course.

It would appear the wind has really got it in for Kate! Here she is bending down to talk to a little girl at the 2013 Place2Be Forum — an organization dedicated to helping children have good mental health. She’s got her clutch in one hand and a bunch of flowers in the other. How she managed to keep her dignity intact we’ll never know!

Rumor has it that when royal ladies attend engagements, they shouldn’t take off their jackets or coats. Apparently, in the Queen’s eyes, removing the extra layer isn’t very elegant. Kate doesn’t always abide by the rules, though. In November 2021 she met Holocaust survivors at the Imperial War Museum in London. She chatted with them and explored the museum — all without her coat on. It must have been nice to know she wasn’t simply there for a fleeting visit!

For royal expert Victoria Arbiter, wearing pantyhose is “the only hard, steadfast rule in terms of what the Queen requires.” Sometimes, though, Kate will prefer to keep her legs bare — as she did in this photo. Mind you, her skin is so flawless that it’s actually pretty hard to tell!

It wasn’t just Kate’s wedding dress that ended up causing controversy, but her wedding hair, too. Kate was supposedly asked to tie it up for her big day. But she apparently wanted to wear it loose, which is how William prefers it. Perhaps her part-up, part-down look was a way of meeting advisers halfway?

We know Kate’s a fan of an off-the-shoulder gown, and we’ve even seen her in a one-shoulder look. But it’s very rare to see her in a strapless dress. This look is particularly memorable, then. The black-velvet number hugged her figure perfectly, and no sleeves meant fans got a glimpse of Kate’s envy-inducing toned arms. William can’t keep his eyes off her, by the looks of things!

Kate has bucked the royal light-nail-polish trend on more than one occasion. When she and William attended a fancy dinner in Mayfair, London, fans couldn’t help but notice her purply-red toenails. It’s not like people weren’t going to see — those gorgeous, sparkly Jimmy Choos sent everyone’s eyes to her feet.

On this outing, it wasn’t the outfit that sent fans into a frenzy. Rather, it was the lack of her engagement ring. Kate is rarely seen without this precious item of jewelry, so when she appeared without it, naturally, lots of questions were asked. But it turns out the reason why was pretty simple. Kate was visiting a children’s hospital and left the sapphire at home to minimize the spread of germs.

When William and Kate spent some time in India back in 2016, fans were excited to see what the Duchess would wear. They no doubt expected extremely lavish, fancy gowns in deep, luxurious shades. Some critics felt she could have pushed the boat out a little more, with British writer Janet Street-Porter calling her “decidedly dreary” in an article for The Independent.

Kate was clearly prepared for Sweden’s chilly temperatures when she visited back in February 2018. But she probably wasn’t prepared for PETA to be hot on her tail once again. After seeing photographs from this event, the organization had its suspicions that the bobble on the duchess’ hat consisted of real animal fur. Kensington Palace publicly announced that the fur wasn’t real, but it made the headlines nonetheless.

It would seem Kate has a soft spot for off-the-shoulder gowns. She wore this gorgeous red dress to the Queen’s birthday celebration in Berlin back in July 2017. It was a little different from the formal attire she usually wears — a bit more floaty and relaxed. But it seemed to suit the occasion nicely. And the ankle-skimming skirt made up for the fact she was showing a little more skin up top!

This beautiful berry-colored number is what Kate wore to Princess Eugenie’s wedding back in 2018. It was a fall wedding in England, so to be honest, Kate should probably have been a little more prepared for a gust of wind or two. Luckily, the Queen seems more preoccupied with something on the floor, so Kate may have gotten away with minimal embarrassment!

Kate seems to be making more than one royal fashion faux pas in this photo. For one, her dress is rather short — definitely a few inches above knee length! And she’s wearing the Queen’s most hated footwear. Then again, maybe one thing the Queen despises more than wedges is pointy heel marks in her perfectly manicured lawn. Who knows?

Kate dug out another pair of wedges for an outing to a children’s hospice back in June 2020. At the event, Kate spent a lot of time on her feet, and she even did a bit of gardening! While the Queen probably wouldn’t approve of her footwear, there’s no doubt the shoes allowed her to get stuck in while still looking a million dollars!

We’ve said it before, and we’ll say it again: the wind is out to get Kate! This time, she was on her tour of Australia back in 2014. And this wasn’t even the worst photo. German tabloids published one where her whole bottom was on display. It’s fair to say the Palace wasn’t at all pleased.

Kate’s brunette locks and this shade of green are a match made in heaven. But that wasn’t the reason the dress made headlines. Back then, the gown’s designer, Dolce & Gabbana, had released an offensive advert. They were in hot water at the time, so Kate’s choice to wear the brand was an interesting one that sparked controversy.

Kate in an Erdem gown seems to be an acquired taste. When photos emerged of the duchess in this blue velvet number on the Cambridges’ trip to Sweden, some fans once again compared the pattern to something you’d find on curtains. The gown was “a little reminiscent of home furnishings,” one person wrote on Twitter. “[Kate] needs a new stylist ASAP,” said another.

When Kate Middleton emerged onto the red carpet for the No Time to Die premiere on September 28, 2021, it was clear she meant business. The sheer sparkly material of this dress combined with the deep, plunging neckline made it one of her most daring looks yet. Plus, some royal watchers think that, after all the controversy caused by Meghan and Harry, this spectacular look was supposed to take her from merely being William’s supportive and loving wife to being something of a guardian angel for the royal family. And like Kate, Meghan’s style has also evolved recently. She’s come a long way from the woman she used to be when she first started dating Harry.

This was one of the first times that Meghan was spotted with her future royal husband. She and Prince Harry went to a game of wheelchair tennis at the Invictus Games in 2017. Meghan was “California chic” here with the white shirt and ripped jeans — but she couldn’t wear casual outfits like that as a working royal.

The big announcement took place on November 27, 2017. While posing for pics at the Sunken Gardens, Kensington Palace, Meghan wore a stylish white coat appropriate for British winter weather. It was a creation from The Label, and they renamed it “Meghan” as a tribute. The future duchess looked great, but some fashion commentators observed that she wasn’t wearing pantyhose like royal women are expected to do. She was still learning back then, though!

Meghan’s first outing as a royal fiancée was meeting fans in Nottingham alongside Prince Harry. She wore another coat, a sensible $790 number from Canadian brand Mackage that matched Harry’s own outfit. Meanwhile, her stylish Strathberry bag, many noticed, bore a strong resemblance to the handbags that are usually carried by the Queen.

For the royal Christmas Day service in 2017, Meghan wore all shades of brown. Her hat was from Philip Treacy, her coat was from Sentaler, and she added a playful touch with some snowflake-themed earrings. Alas, the hat was considered a bit of a fashion fail, with some people unflatteringly likening it to a not-so-nice emoji.

Meghan’s outfit here is very safe — perhaps a little too safe? While visiting Cardiff in January 2018 she had on a black Stella McCartney coat plus trousers from a Welsh company, Hiut Denim. She also carried a green handbag, which some thought may have been in tribute to the Welsh flag.

Meghan was still wearing coats the following month, too — fair enough really, as it was still chilly outside. Once more she was seen in clothes that paid tribute to the region hosting her, which is something all royals seem to do. The duchess had on a tartan coat, tartan being a classic Scottish pattern, and she carried a bag from Edinburgh’s own Strathberry brand.

For International Women’s Day 2018 Meghan and Harry went to Birmingham to attend a careers event. Meghan color-coordinated with her fiancé for this outing — both of them were wearing navy blue. Yet while Meghan’s J-Crew coat was very stylish, some fans thought it was a little too shapeless on her, swallowing her up.

Meghan tried something more figure-hugging when she visited Northern Ireland in March 2018. She wore a Mackage coat again, this time in beige, and a pencil skirt in a flattering shade of green. As for the sweater, it was the same one that Meghan had worn in an engagement snap, and it had been designed by her good friend Victoria Beckham.

Meghan’s daring side began to show a little more as the wedding to Harry crept closer. For a reception in April 2018 she pulled out a sexy — but not too sexy — little black dress from the brand Black Halo. The dress was called “the Jackie O,” and versions of it have been seen on celebs including Kim Kardashian and Scarlett Johansson.

Anzac Day is for paying tribute to the armed forces of Australia and New Zealand, so of course, a royal wouldn’t wear anything too eye-catching for this service. Meghan dressed appropriately in a long gray coat by Smythe, a black blouse from Stella McCartney, and all-black, toned-down accessories. The only colorful thing was a red poppy, the symbol of remembrance.

It wouldn’t do to wear anything too attention-grabbing the day before the wedding. You want your wedding dress to be the center of attention, after all. So when Meghan checked into the Cliveden House Hotel with her mom Doria, she wore a stylish but simple navy-blue dress from Roland Mouret.

One of Meghan’s first events after becoming an official royal was Prince Charles’ 70th birthday celebration. She stunned in a light-pink custom-designed “Flavia” dress from the company Goat Fashion and a matching hat by Philip Treacy. She looked lovely, but this outfit seemed a lot more “Duchess” than “Meghan.”

Meghan wowed with a similarly colored outfit for the 2018 Trooping the Color parade. It looked as though she had found a good color scheme for formal royal events and was sticking to it. This time, her light-pink outfit was from Carolina Herrera, though the hat was once again from Philip Treacey. 

Meghan’s outfits usually adhered firmly to royal protocol during this time of her life. She wore a stylish but sensible dress from Dior for the RAF event and matched it with a hat by Stephen Jones. You’ll note her skirt goes down to her knee — a rule royal women are expected to stick to.

As 2018 continued, Meghan kept it up with the long dresses and monochromatic tones. For her trip with Harry to Dublin in July, she wore this long gray gown from Roland Mouret. It looked professional, but perhaps a little dull for a duchess — and some fans complained the fit was so bad that her bra looked visible.

This was another event where the participants had to dress solemnly, as befitted the occasion. Harry was in his military uniform, and Meghan wore a long black Emilia Wickstead frock, plus a hat from her seemingly favored brand Philip Treacy. It wasn’t particularly remarkable in terms of style, but that made it just right for a memorial service.

Meghan decided to go with something a bit more modern for the Centenary of the Armistice Service. Along with her black beret hat and the all-important poppy, she wore a dark-blue skirt suit that fell to under the knee — but only just under the knee. She seemed to be taking a few more risks.

Meghan was still in muted colors as she embarked on her second year of royalty, and her pregnancy was starting to show as well. For an engagement at the National Theater, she wore a floaty-skirt dress — one that had been adjusted to make the hemline longer and thus more appropriate for royal events.

Meghan was getting bolder with color as she approached the end of 2019. This dress from October that year was perhaps rather shapeless on her, but it was a stylish shade of purple. And as befitted Meghan’s dedication to environmentalism, it was a recycled piece. She’d worn it previously in the January.

Meghan and Harry shook the world in early 2020 when they announced they were stepping down as senior royals. Suddenly, even more eyes were on them than usual. When Meghan attended one of her last royal events — the Endeavour Fund Awards — she wore a slinky blue creation by Victoria Beckham. Was it her way of defying the media?

This trend of wearing eye-catching colors continued throughout March 2020. For the Mountbatten Festival that month, Meghan showed up in a Safiyaa dress in bold red. This helped her present a united front with Harry, who was in his red military uniform. And perhaps there was also an element of “show the critics what they’ll miss” here.

Meghan’s last proper royal outing was at the Commonwealth service at Westminster Abbey. Once again, she wore something bright and eye-catching — this time, an emerald-green creation from Emilia Wickstead. Were her “goodbye” outfits, including the green cape, a return to the style of pre-royalty Meghan?

In 2005 Meghan Markle’s life was very different. She didn’t wear evening gowns but the most casual of casual wear — jeans, t-shirt, baseball cap. At Kari Feinstein’s Pre-Emmy Style Lounge, she was snapped looking at baby clothes, not having the slightest idea her eventual children would be British royal family members.

Back in the day, young Meghan Markle wore cute summer-y dresses and open-toed shoes to parties. A little strappy dress like this one probably wouldn’t be appropriate for most royal events, but it looks great on pre-fame Meghan. You’ll note her jewelry game was on point even back then, too.

By 2012 Meghan had won her big role in Suits, and her style was evolving. Here she is at the HBO Luxury Lounge wearing bold black and white. You’ll note her hemline is a lot higher here than it would be in the future, too, and she’s showing off her gorgeous legs in a way royalty can seldom do. 

Meghan seemingly had more fun with her wardrobe before she joined the royal family. Take this one from TV Guide’s Hot List Party in 2012. She wore a stylish and eye-catching multi-colored strapless dress and carried a funky cylinder-shaped gunmetal clutch. And she wore minimal jewelry, which worked with the look.

Suits-era Meghan wore this undisputedly sexy red dress to a GQ party in 2012. Check out how low-cut it is! And also check out that nail polish on her hands and feet. As a royal, Meghan wouldn’t be allowed to wear bright varnish most of the time, because the Queen famously hates it.

2013 was a big year for Meghan in many ways. Suits was still going strong, but on the other end of the spectrum, she got a divorce from her first husband, Trevor Engelson. Perhaps this slinky pink gown was a revenge dress? Whether it was or not, it looked fantastic on her.

Meghan seemed to hop back to the 1970s to find inspiration for this outfit. She wore an Isabel Marant “Mallonia” Jacquard dress to the USA Network 2013 Upfront party in New York City, along with some black shoes and a chunky bracelet. If you want the dress for yourself, it’ll set you back $1,590!

Meghan’s always rocked bright whites. For an appearance at the MuchMusic Video Awards in Toronto in 2013, she wore this sexy, short white gown that was just the right mixture of dressy and casual. Not many people behind the barrier at this red carpet event are looking at Meghan — but that would soon change.

This outfit was New York Meghan at her best. For her appearance at the Lincoln Center in 2014, she wore another short dress, this one with risqué slits in the front, and a studded leather jacket thrown over her shoulders. It was almost a punk look, the sort of thing a royal probably couldn’t get away with.

Meghan wasn’t seen in pants much when she was a royal, but she clearly liked wearing them before. Here she is at the Four Seasons for NBC’s 2015 New York Summer Press Day wearing all white once more. And this is another very risqué outfit. You can see her bra, for example, and there’s no doubt that was on purpose!

One of Meghan’s most daring and stylish outfits was this shorts and blazer combo she wore to the Today show in 2016. A tribute to her hit show Suits perhaps? She wore the co-ord quite a lot during her time as an actress, and it was sadly missed when she became a royal. Maybe it’ll be back one day?

Remember how Meghan has often been spotted in Roland Mouret pieces? Her association with the brand goes back years. The duchess is friends with Mouret himself, so she was one of the attendees at his private dinner party in 2016. As expected, Meghan wore one of his gowns, and she carried a snazzy beaded bag from Antik Batik.

Meghan wore shorts again, this time striped ones, for a July 2016 appearance on Today at the Rockefeller Center. It’s thought that Meghan had had at least her first date with Prince Harry by this point, having been introduced to him by a mutual friend. You can understand how he would’ve been dazzled by her Hollywood chic.

So once Meghan left the royal family, she was free to wear whatever she liked again. But what had she learned? Well, some think she definitely discovered the art of sending coded messages via clothes. When she gave her tell-all interview to Oprah she wore a dress with a lotus motif — the lotus flower signifying rebirth.

Meghan still seemed very into her camel-colored coats even after she’d left the royal family. She wore another one, a Max Mara “Rispoli” style, for a meeting at the UN in September 2021. And her black skirt was from her old friend Roland Mouret, an “Arreton” wool crepe pencil skirt. 

Meghan wore another very professional-looking outfit during her stay in New York City. This one was all dark blue, with pants instead of a skirt and an “Arianna” sweater from Giuliva Heritage. And she had on a very significant accessory — a gold Cartier watch her late mother-in-law, Diana, is said to have owned.

During their New York trip, Harry and Meghan visited a school in Harlem, and Meghan was back in bright colors for the event. Her whole outfit was red, a color she definitely seems to like. Her ensemble was all from the brand Loro Piana, and the cashmere coat alone was worth $5,840.

Meghan debuted a whole new look at the Global Citizen Live concert in September 2021. She was back in a short white dress, similar to the ones she’d worn before becoming a duchess, but this one was perhaps a little more sophisticated. It’ll be exciting to see what happens as her style continues to evolve! In the meantime, here are what we think are Meghan’s best looks to date. They really turned heads...