Kate Middleton's Most Talked-About Looks To Date

Catherine, Princess of Wales knows that whenever she goes out, what she wears will be scrutinized. She is one of the most photographed women in the world, and she has become a true fashion icon in recent years. So, eagled-eyed fans notice everything about her wardrobe — from subtle symbolism in her jewelry to a (gasp!) repeated outfit. There’s no doubt that the beloved Kate Middleton has got royal style down to a fine art, but that doesn’t mean her looks are boring. Sometimes, the princess is prepared to push the boundaries, and people love to talk about it.

1. The wedding dress

Naturally, one of Kate’s most talked-about outfits ever is going to her wedding dress. With its gorgeous lace sleeves and nearly 9-foot-long embroidered train, Kate’s gown was, for many, utter perfection. "Miss Middleton chose British brand Alexander McQueen for the beauty of its craftsmanship and its respect for traditional workmanship and the technical construction of clothing," shared the Palace on the very day that William and Kate tied the knot. But that didn’t stop it from causing a ruckus; the stunning design actually sparked a lawsuit. A designer called Christine Kendall took Alexander McQueen to court, maintaining that the fashion house had used her original ideas without consent. By the looks of things, the case hasn’t been resolved.

2. Roller disco

Although she may come across as the poster girl for grace and decorum almost all of the time, we like to think that Kate is 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-princess 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.”

3. Engagement dress

The outfit that 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. Thankfully, the brand, Issa, was able to relaunch in a U.K. department store in 2015. Given its popularity, they, of course, chose to include a recreation of Kate's iconic wrap dress in a range of colors. And what's even better? They slashed the price to around $124. 

4. Fashion show

Taking a look at this see-through dress now, we can’t even picture it as something that Kate Middleton would ever wear. But she wasn’t always a princess. Once, she was just a regular student, and she wore this outfit during a fashion show fundraiser in her college days. 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.” Not a bad response for a dress that Marie Claire reports as costing a bargain $58!

5. Caught in the wind

Sometimes, the wind can be a real “b” word. Kate knows this, having fallen foul of 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! As you can imagine, the fashion faux pas picked up quite a bit of attention, especially among royal-protocol experts. Many noted how sewing weights, or even a few carefully placed pennies, could have avoided the whole mishap. 

6. Wedges

It’s got to be said: the Princess of Wales loves a wedge. It’s a pity the Queen reportedly didn’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 never liked to look back on those times. Understandable, really. Luckily, eagle-eyed fashion fans have noted that Kate never seemed to wear the offending wedge whilst in the company of Queen Elizabeth, opting instead for a court heel or pair of flats.

7. Dress from the wrong place

When traveling to another country, royals like to make sure that they wear the colors and fashions of their hosts. They are diplomats after all, so it helps to build bridges. And It looked as though Kate tried to do just this back in 2012 when she and William flew to the Solomon Islands as part of the Diamond Jubilee tour. No doubt she was meant to be wearing a dress from this region. But it turns out that what she actually had on had been made miles away in the Cook Islands. Whoops!

8. 2018 BAFTAs dress

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 to the Time’s Up campaign, but the princess seemingly ignored the dress code and stepped out in a floor-length dark-green number instead. Royals aren’t meant to engage in any politics, you see. Even so, Hello reported that the almost $4,000 Jenny Packham gown may have been a nod to the Suffrage Movement that used green to signify hope. And then there's the easy-to-miss black belt, which some thought was Kate's discrete way of showing her support. Of course, the palace never passed comment on either part of the outfit.

9. Jubilee dress

Just look at Queen Elizabeth 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, though. The Alexander McQueen design seemed to have been tailored to Kate's needs — with a lower hemline and long sleeves. And while the princess looked stunning onboard the Spirit of Chartwell at the Thames River Pageant, she did receive criticism for taking the focus off of her grandmother-in-law. It was the Queen’s Diamond Jubilee, after all.

10. Ascot

What’s wrong with this outfit, we hear you ask? Most people would take one look at the Alexander McQueen midi dress and think that it was 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. Many felt the dress wasn’t long enough and that, because of the translucent material, Kate was showing too much skin. Vogue likened the unwarranted reaction to Kate's lacey look to a similarly prudish response that targeted Wallis Simpson back in 1937 after she was photographed in a dress with a sheer panel. It seems like things haven't changed in almost 90 years — you really can't please everyone. 

11. Too perfect post-birth

Kate looked positively radiant when she stepped out after giving birth to Charlotte on May 2, 2015 — well, the same could be said for all of her post-birth appearances, come to think of it. But some people watching were still able to find a reason to complain. Apparently, on this particular occasion, they thought the then duchess looked “too perfect” for someone who’d had a baby just hours before. In our opinion, the buttercup-print Jenny Packham dress was just right.

12. Fur-lined gloves

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 that the princess' mittens had been made with real fur. According to sources, the Restelli Guanti set was lined with possum fur. Following the controversy, Queen Elizabeth made a public announcement that she would never dress in real fur again — but we don’t know if Kate followed suit.

13. Bright nails

Word has it that the Queen wasn’t a big fan of bright nail polish. According to sources, If she were ever going to sport painted claws, it would have been a very subtle, light pink shade. Kate bucked this trend when she arrived at an evening event at London's Natural History Museum in 2017. Fans’ eyes were instantly drawn straight down to her toes, which were painted a bright red. On the then-duchess, it looked gorgeous. But then again, Kate could make neon green look classy.

14. A busy print

When Kate stepped out at the 100 Women In Hedge Funds Gala Dinner 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.” While another tweeted, “Kate is dazzling ok? Dazzling. But that print is something I'm certain my mother chose for curtains back in 1984. Don't hate. Love Kate.” Clearly, the $4,560 price tag didn't translate to a legion of fans, then.

15. Shorts

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 princess, 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. Kate's boat was representing The Royal Foundation, the Prince and Princess's charity. Whereas William was racing on behalf of the charity Child Bereavement U.K. Unfortunately, even with her sporty get-up, Kate and her team still finished last. William, on the other hand, came in a respectable third place. 

16. An off-the-shoulder look

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. Given that the royal family is assisted by an entourage of staff, we'd like to think that back-to-front blunders simply wouldn't be possible!

17. Back-to-front blouse

Kate has been known to step out with an item of clothing on back to front, though. Both times she has been seen in this purple Gucci blouse, the buttons have been at the front. And just like the zip drama with the $2,000 off-the-shoulder Barbara Casasola gown, fans were tripping over themselves to point out the perceived mishap. This time, though, they were right! If the blouse were worn as Gucci intended, then the buttons would actually run up the back. Kate clearly prefers it this way around. And if anyone can pull it off, it’s her!

18. Skinny jeans

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! And though Queen Elizabeth was only pictured in pants once during the Royal Tour of Canada in 1970, plenty of other royal women have pushed the boundaries and donned a pair. Princess Diana, Meghan Markle, Sarah Ferguson, to name a few.

19. Red to Wimbledon

This striking red dress marked a turning point in Kate’s Wimbledon fashion. Up until 2015, the outfits Kate wore to the tournament allowed her to blend in relatively well. Not this year, though. 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. There was good news for fans of the elegant number, too, as they could bag the very same dress for $310.

20. Christening dress

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.” Thankfully, the bad press clearly didn't ruffle Kate's feathers, though. Since 2015, she's recycled the look on more than one occasion. First up she wore a pale-yellow version of the same design to attend Harry and Meghan's wedding. And then in 2022, she wore the exact christening outing at an event to honor Australians and New Zealanders who lost their lives at war. Some say boring, we say thrifty!

21. Marilyn moment

It was at India's Delhi War Memorial that Kate had her Marilyn Monroe moment — unintentionally, we might add. Just as she 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. The quick-thinking princess, thankfully, didn't let herself down, and she was able to avert a true disaster by grabbing the hem. Maybe Kate should have taken a leaf out of the Queen’s book and gotten weights added to the hems of her dresses.

22. Unpedicured feet

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. According to experts, Kate's feet showed tell-tale signs of having worn heels a little too often. One even suggested that the larger size of the joint on her big toe could lead to arthritis if she doesn't kick the heel habit. Ouch!

23. Too much knee

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 princess 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 Eugenie’s dress in comparison! Hemlines aside, fans were pleased to see Kate take a slight detour from her classic navy looks, and the baby blue number became yet another fashion triumph for the princess — even if it was a little on the short side!

24. Sheer and a slit

When Kate stepped onto the red carpet at a U.K. film premiere in this sexy number, the 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 in the flowing piece. 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.

25. Too short?

It would appear that 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 — a London-based organization dedicated to helping children have good mental health through emotional support in schools. 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! But honestly, we’re never failed to be impressed by Kate Middleton. She will not be beaten by the wind!

26. Taking off her coat

Rumor has it that when royal ladies attend engagements, they shouldn’t take off their jackets or coats. Apparently, the Queen believed that removing an extra layer wasn’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, at least! And who would want to hide that exquisite military-themed blouse?

27. No tights for Kate

For royal expert Victoria Arbiter, wearing pantyhose was “the only hard, steadfast rule in terms of what the Queen required.” Sometimes, though, Kate will prefer to keep her legs bare — as she did in this photo. When she does wear tights, though, the public reaction is off the charts. According to the Daily Mail, just the sight of Kate out in public wearing pantyhose caused sales of the product to soar. Mind you, her skin is so flawless here that it’s actually pretty hard to tell whether she's wearing them or not.

28. Wedding hair

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. According to Ashley Pearson, one of Kate's aides, “Royal sources tell me that the royals indicated very strongly to Kate that they would prefer her to wear her hair up for this very special occasion. However, Kate had her heart set on wearing her hair down with long flowing curls, which is her favorite way to wear it, and actually William’s favorite as well.” Perhaps her part-up, part-down look was a way of meeting advisers halfway? Either way, the decision broke 350 years of royal tradition.

29. Strapless velvet

We know Kate is 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. So this look at the Sun’s Military Awards was particularly memorable, then. The black-velvet Alexander McQueen 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! As for Harry, well, he just seems excited to be there!

30. Dark toenails

Whether she goes au naturel with her nail color or pushes royal limits with a bolder hue, it seems Kate can't avoid harsh scrutiny. And given that Kate has bucked the royal-approved light-nail-polish trend on more than one occasion, there's been plenty of chances for critics to pitch in their two cents. 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.

31. No engagement ring

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. Given that the ring comes with a hefty price tag, we think that was probably a wise decision for more than one reason.

32. India dress

When William and Kate spent some time in India back in 2016, fans were excited to see what she 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. In Kate's defense, she was playing tennis, so even sporting a dress and wedge heels was pretty impressive by most people's standards. 

33. Fur beanie

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 was made of real animal fur. Kensington Palace publicly announced that the fur wasn’t real, but it made the headlines nonetheless. And in response, the director of PETA even went on to seemingly backtrack and praise Kate's decision.

34. Off the shoulder again

It would seem Kate has a soft spot for off-the-shoulder gowns and taking risks with the wind. 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, too.

35. More pesky wind

This beautiful berry-colored number by Alexander McQueen is what Kate wore to 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. Still, her fuchsia frock and matching accessories still managed to look flawless for most of the day. And luckily, the Queen seemed more preoccupied with something on the floor at the moment the wind struck, so Kate may have gotten away with minimal embarrassment!

36. Wedges and miniskirt

To the untrained eye, Kate's outfit looks normal— floaty dress, practical blazer, and sensible shoes (for heels). But in actual fact, Kate seemed to make more than one royal fashion faux pas as she strolled alongside William in front of Buckingham Palace. For one, her dress was rather short — definitely a few inches above knee length! And she was wearing what was the Queen’s most hated footwear. Then again, maybe one thing the Queen despised more than wedges were pointy heel marks in her perfectly manicured lawn. Who knows? Either way, the pair were headed off to their honeymoon, so perhaps we can cut them some slack.

37. More wedges

Kate dug out yet 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 have approved of her footwear, there’s no doubt the shoes allowed her to get stuck in while still looking a million dollars! Bonus points for Kate here, as the flowing floral number was from eco-conscious clothing company Faithfull The Brand. 

38. The wind — again

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, when helicopter blades unexpectedly lifted her $367 Diane Von Furstenberg midi dress. And this wasn’t even the worst photo. German tabloids published one where her whole bottom was on display — a controversial move that caused a media stir around the topic of privacy. It’s fair to say the Palace wasn’t at all pleased.

39. Green Wimbledon dress

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, naturally, sparked controversy. And to add insult to injury, Kate's bag was also by D&G. Still, there's no denying that the green get-up suited Kate perfectly.

40. Another controversial Erdem gown

Kate in an Erdem gown seems to be an acquired taste. When photos emerged of the then-duchess in this blue velvet number on the Prince and Princesses' 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. Hopefully, Crown Princess Victoria and Prince Daniel of Sweden weren't as offended by Kate's dress choice. 

41. Stealing the show

When Kate Middleton emerged onto the red carpet for the No Time to Die premiere on September 28, 2021, it was clear that she meant business. The sheer sparkly material of this Jenny Packham dress, combined with the deep, plunging neckline, made it one of her most daring looks yet. And the gold get-up didn't go unnoticed by 007 himself. According to sources, Daniel Craig told Kate that she looked "jolly lovely" as she arrived at the event.