Kate Middleton: Her Best Looks, Past Loves, & Latest Flubs

Kate Middleton is the exact epitome of royal elegance and grace. She’s a demure creature of sophisticated brilliance in more ways than one. But the Duchess has a down-to-earth side too. She can be sporty and goofy and even acts like a regular person sometimes.

Behold all the times that the Duchess of Cambridge was caught doing something totally goofy or just looked jaw-droppingly gorgeous.


We all have exes. But most of us are able to put those dabblings in the past. Not Kate Middleton! Someone scrounged up these photos of the Duchess in her pre-royal days. Looks like fun, girl. But we’re glad you found your real-life Prince Charming.

Raisin Monday

This is a photo taken at a St. Andrews University event called “Raisin Monday.” It’s a freshman tradition that’s over 600 years old!

Do Duchesses Go Clubbing?

Does a lion roar? The answer to both is yes! Here’s Kate out at the club to blow off some steam. Then again, this was long ago during her more carefree days as a student. Now that she’s married to royalty (and is a mother!) we won’t likely see her out and about like this.

A plunging neckline…

Photos of Kate before she became a royal are always fascinating, since it gives us a taste of what her fashion sense really is, without all of the restrictions that come with her role of being a Duchess and future Queen. Here, we see her in the summer of 2006 wearing a rather revealing red polka-dot Issa wrap dress while she was watching future-husband Prince William play polo. Kate would wear another, albeit more modest Issa wrap dress when the couple announced their engagement to the world in 2010.

An Interesting Pose

Hey, its a crowded car… what do you expect? The Duchess of Cambridge has quite a wardrobe. Sometimes it lets her down, but she has plenty of favorite designers. She’s been seen in Sarah Burton’s designs. Burton is part of the house of Alexander McQueen. It helps Kate balance her more severe British-ruling class needs with her very soft, feminine motherly side.

Wide range of emotions

Kate sure shows her moods in her facial expressions. Check out all these crazy faces, exhibiting everything from shock to amusement.

A hot body…

Needs cold water!

We’ll probably never get to see Kate Middleton in a bikini ever again, now that she’s the wife of the (likely) future king of England. So enjoy these ones! She certainly is…

On a boat

She wore an itsy bitsy teeny weenie little white bikini. And her hot sis Pippa wore one on this day, as well.

A real athlete

Kate’s shown time and time again that she’s a terrific athlete. Here she is shooting a little b-ball at a charity event. It’s hard to stay covered when you’re so active.

Swoosh! She shoots…

Anddddd… Again!

We can’t blame you, Kate. If ya got it, ya flaunt it! And she definitely has got it.

Making faces

As we’ve seen, Kate is really good at making faces. I think she’s a lot more goofy when she thinks she’s not being watched by photographers! What on earth is going on in this scene to make Kate pull such a funny face?

Salute the Duchess

Wow, Kate’s legs seem to go on forever. And the fact that the wind is intent on pushing her skirt up higher certainly doesn’t help matters.

Kate single-handedly turned her signature shoes, L.K. Bennett Sledge nude heels, into international bestsellers. They retail for around $350 per pair.

Modeling days

Did you know that William first met Kate when she was modeling for her friend’s fashion line? It was back in 2002. These are a few of the getups she wore… it’s hard to imagine her wearing something like this these days. While the lad she modeled with on the left might bare a passing resemblance to William from behind, it was actually his roommate at the time, Fergus Boyd.

The Royal version

This is what Kate’s style looks like these days, as the mother of the future King (or Queen!) of England.

It’s still sassy and sheer, just a lot more polished and elegant. I’m certain her mother-in-law Diana would have approved, were the two ever able to meet.

The wind, it never ceases

Oh, how embarrassing! She’s meeting a dignitary and has to cover her bum with her hands the entire time. Kate’s looking cheeky here!

Newlywed bliss

Here’s the brand-new Duchess, just days after her royal wedding. I sincerely doubt that she intended to be snapped by the paparazzi during this trip to the grocery, but I love her all the more for it.

Check out Diana’s ring on Kate’s blinged-out finger — d’you suppose Di ever pictured it riding around on a shopping cart?

Leaving an offering

On a recent trip to India, the Duke and Duchess laid a wreath at the national war memorial in Delhi. Kate struggled to control her £1,700 dress during the solemn occasion. Is she channeling her inner Marilyn Monroe?

I wonder why she’s not allowed to wear pants at outdoor events, given her history of upskirt issues and the paparazzi’s obsession with her?

Back on the scene

Wow, Kate was really quite the party animal back in the day! Here she is for a girl’s night out with her sexy sibling Pippa. It’s pretty clear that they’re having a blast. Sisters on the scene!

Sly smile

She looks quite happy about something, doesn’t she? In a “cat got the canary” sort of way. I wonder if she met up with William this night.

There’s Nothing Like Spending Time With the Girls!

This is a wonderful display of lovely legs!

Did you know that Kate is actually a qualified Scuba diver? She frequently jets off to the island of Mustique in the Caribbean, where she’s able to hone her Scuba skills in privacy.


This is a much more casual look than we’re used to seeing on the Duchess. But wow, check out her guns in that little white t-shirt!

I’m probably mis-reading her shirt, but doesn’t it look like it says “wild thing?”


OK, so none of us need to be judged in our workout wear, at all. But c’mon, this is Kate Middleton… doesn’t she realize that there are non-VPL panties out there?

Here’s the future Duchess, just out for a little row. Hottie!

Pantyhose Queen

Did you know that Middleton brought back pantyhose in a BIG way? Whether you call them hosiery, pantyhose, hose, or tights — “suntan” or “nude” colored legwear hasn’t been fashionable since… I don’t know when.

Check out what they do for Kate’s already-toned legs, though, and you’ll be buying some soon. Not to mention, they really come in handy on those blustery days that Kate’s always encountering.

Careful, there!

This photo surprises me… you’d think by now Kate would have learned how to enter and exit a car. Or to find undergarments that kept things to the imagination a bit more.

We all have fashion faux-pas from time to time. But most of ours aren’t plastered all over the news.

Another view

This is such a cute, but sexy, look on Kate. The way she pairs that little dress with the racy boots is just too perfect for a young Duchess.

And check out her coat lining… meow!

What happened here?

Oh no, what happened in this scene? Kate’s obviously out for another night out with her ladies-in-waiting, and it looks like there’s been a mishap.

Doesn’t the girl next to her look as if she could be William’s sister? For real?

Party all the time

Kate is looking slightly worse for the wear in this photo… not quite buzzed, but maybe halfway there. And she’s in her trademark “party girl” suede knee-high boots. Think she still owns those? I bet more than a few museums would like to get their hands on them.

Even worse…

and kind of a hot royal mess here. She’s received a lot of flak over the years for her party life, but who didn’t have their share of fun times in college?

Is that Prince Harry she’s dancing with, by the way? Cute!

Harry and Kate’s sister Pippa were rumored to be a couple for a while. How odd would that be!

Sense of humor

In almost every photo you see of Kate, she’s either smiling or laughing. She loves to help others, and she always looks good doing so.

Rubber duckie

It’s the Royal family like you’ve never seen them!

Obviously, this is a joke, featuring professional Will & Kate impersonators. But it’s still a lot of fun — these photos look soooo real.

Too far?

In this age of social media and constant access to celebs and dignitaries, are real photos like this so far off? Will the next generation of the British monarchy post *actual* photos like this to their Instagram accounts?

All dolled up

She sure cleans up well, doesn’t she?

Even when she’s dressed regally, Kate finds a subtle way to show off her toned body. If you’ve got it, flaunt it!

The Duchess of Yes!

It’s easy to see why Kate has become an international fashion icon. She simply wears the most gorgeous clothes, and looks absolutely stunning in them. Kate makes it look completely effortless!

Though she’s loved for being down-to-earth, Kate has come under criticism lately for her willingness to recycle clothing. She’s frequently spotted out in clothing she’s already been seen in, and some have wagged their tongues over the practice. Guess you just can’t win them all, Katherine.

Expecting much?

This is such a candid shot — Kate obviously knows that she’ll be photographed “out and about” in this pregnancy shot. But she’s dressed very casually, and it looks like the wind is once again conspiring to reveal more than she intended. In this case, her adorable baby bump!

Those baby blues

And here she is, dressed in full Duchess regalia. Even while pregnant and sporting a bit of belly, Kate exemplifies style and grace. Her mother-in-law would be proud.

One member of the healthcare team assigned to Katherine’s deliveries recently said: “We weren’t actually at the birth but were behind the scenes. We were all on call for three months – my husband did the childcare for three months! You never know when you need to be called. You need to be in town and available. If you are at a party you need to have your car keys at the ready. No drinking!”

Duty calls

Here are Kate and William on an official visit to Australia. That’s a look of love if I’ve ever seen one.

At a recent flower show, the Duchess revealed what her nickname for William is. He asked about some blooms he had been admiring, and Kate replied “Babe, we’ve got those. We’ve got loads of those.”

Mommy dearest

And here’s Kate in her newest role: motherhood. She has two lovely children, a son named George and a daughter named Charlotte.

I wonder how it feels to be the mother of the future monarch! Those are some privileged nappies.

Everything’s covered

Kate’s the epitome of elegance, and with her handbag carefully placed to avoid any peepshows. In fact, she frequently uses her handbags to keep herself covered.

That hat is to die for!

Bravo, Bravo

Jolly good show! It’s been fun to watch Katherine’s transition from her wild-child student days to her role as the Duchess of Cambridge. We can’t wait to see what kinds of fashions she’ll showcase next!

Shopping for more clothes

Although she presumably has designer fashions delivered straight to her doorstep, Kate has been known to enjoy a good shopping trip every now and again.

Which designers does the Duchess prefer?

Kate has a range of favorite fashion designers. Some of the names she’s partial to include Alexander McQueen, Mulberry, Reiss, Emilia Wickstead, Zara, Issa London, Temperley London, Jenny Packham, Le Chameau, J Brand, and Aquatalia.

Kate has the last laugh

Here’s Kate in yet another gorgeous dress. If she’s ever down in the dumps, she certainly doesn’t let the public know about it — there’s always a bright and beaming smile across her face.

She’s using her handbag as a shield yet again here. Good girl!

Shoes to DIE for

Now, if you’re not allowed to wear clothing that’s too revealing but you have a penchant for showing off your best assets, this is how you do it. You find the sexiest, most flattering heels out there and you pair them with an elegant nude-colored dress.

This is one of our favorite looks on Kate, ever!

Another flashback

Those legs just won’t quit. Ad isn’t it crazy to see a future Royal out and about in tight jeans?

Here’s Kate back in the day, on another big night out. Looking good, K!

She’s got leeeegs

Kate’s results are clearly the result of good genes, since her sister is blessed with the same gorgeous gams. But it you want to improve your own legs, experts recommend a combo of cardio, squats, and lunges. Keep up a consistent routine and you’re sure to see results in no time.

Sisters do sheer

Kate really seems to love sheer dresses. Perhaps wearing a see-through dress reminds her of the time she first met, and bedazzled, Prince William!

Ah, nostalgia…

Pippa’s turn

Here’s Kate’s little sister Pippa in a very similar (but not as royal) dress. Who wore it best?

We know it’s not really a competition, but despite Pippa’s clear cuteness, nothing can compare to Kate’s gorgeous style!

Who did it first?

Who do you think made the tongue-in-cheek face first? Did Kate learn that from Will, or vice versa? You have to admit, it looks pretty cute when they do it at the same time.

Hanging with the in-laws

When Kate spends time with her in-laws, it’s a little different than it is for the rest of us. Lucky for her, she seems to have charmed William’s grandmother (who just happens to be the Queen of England)!

Jump around!

Here’s Kate visiting the 2014 Commonwealth Games in Glasgow, Scotland. She’s participating in a game called “three tins,” which involves jumping over three cans. Sounds silly but Kate is obviously good at it!


We have no way of knowing what this conversation is all about, but Kate’s expression makes it look like the two women are engaged in some seriously shocking gossip. Dish it, Duchess!

Mother of the year

Kate is not afraid to take a hands-on approach to raising her children. She runs around and plays with them just like any normal mother!

Royal Zoo

Parenthood sure suits William and Kate. Here they are with son George, visiting the Taronga Zoo in Sydney, Australia. That cute little critter is called a Bilby.

Sheer ridiculousness!

On Kate’s third official engagement, she flipped pancakes at a charity fundraiser in Belfast. She looks a little bit nervous about the task, but did a great job.

Always athletic

Kate’s always been athletic, and seems to excel at just about any sport she tries. Here, she’s concentrating to return a volleyball serve. Wonder if she’s wearing heels!

Seeing red

Here’s Kate in one of her gorgeous ensembles – this one a pretty red dress. Her expression is hilarious, though. It looks like she’s about to catch a ball that’s been tossed to her.

Bad hair day

We all have bad hair days, especially when we have to be out in the elements. It’s not often that we see Kate with a hair out of place, though!

Back in the day

Kate and William really loved to cut loose back when they were in their carefree university days. It looks like they’re having a real blast here!


Here, it appears that Kate has just spotted a unicorn flying over a rainbow. She seriously looks awestruck. Maybe she just realized that she’s a Duchess!

University cut-up

Here’s Kate back in her university days, before she had to worry about her public image. She sure looks like a lot of fun!

Just Playing Around

Everyone needs a break now and then, and the royal couple are no exception. Here, Will and Kate frolic on a snowy day in the Alps. This photo was taken in 2016, and their last ski trip was all the way back in 2012! It’s a well-deserved getaway.

The Queen of Casual

There are not many people who can pull off such a wide range of styles. From sporty to fit-for-a-queen, Kate always looks great. Here she is in some rugged athletic wear and she’s just as stylish as ever. In fact, has she ever looked bad a day in her life?

Bhutan Visit

In April 2016, Kate and William visited Bhutan, where they visited with the country’s King and Queen. The Duchess donned a Bhutanese-inspired ensemble for the meeting. How appropriate! Kate also tried her hand at archery during the visit – and wore her signature high heels for the entire event.

A Royal Ride

Prince George got a special treat when he was presented with an Avanti mini bike while on a tour of Australia with his parents. Kate wore a lovely knee-length green coat for the ceremony and looked delighted at the lavish gift. She has said more than once that George has become spoiled.

Down At Their Level

Even at official state ceremonies, Kate is a very hands-on mom. This is the royal family arriving to Canada, and it was their first official trip overseas as a family of four. They were greeted by Canadian Prime Minister Justin Trudeau as they exited their plane.

Sweat It Out!

The family that plays together, stays together. If that’s true then the royal family is all set! You can tell from this photograph how much William, Kate and Harry love each other and have fun together. Reportedly, on this day Kate was extra giggly and was clearly enjoying the quality time with her husband and brother-in-law.

She’s Always Game

Kate seems to make the most out of every opportunity, doesn’t she? In this photo, she and William are on a tour of the Solomon Islands. They are putting on a brave face, as they had recently been subjected to a photo hack which exposed their most intimate pictures to the world.

Simply Stunning

When we think of red carpet film premieres, we tend to envision Hollywood movie stars like Angelina Jolie or Jennifer Lawrence. But the Duchess of Cambridge topped them all at the world premiere of Mandela: Long Walk To Freedom in London, December 2013. Demure yet sexy, Kate’s dress is absolutely gorgeous.

Pretty In Pink

Even when she’s dressed in a neutral color palette, the Duchess frequently spices things up with a powerful, and fun, pop of color. This time it’s in the form of a bright fuchsia coat that shows she’s up for a good time even while serving her royal duties.

A Charmed Life

Have you ever seen a photograph of Kate where she looks sad, tired, or disheveled? No one has! Even though she’s faced her fair share of personal setbacks, she always has a smile and a laugh handy. Being a beautiful duchess might have something to do with that…

Look! Up In The Sky!

It’s not a bird or a plane, but just the royal couple paying tribute to veterans who died in the Battle of the Somme. They were visiting France just for the solemn occasion. Kate looked stunning in a cream blouse with a black printed skirt, all topped off by a black fascinator in her hair.

All Smiles

There’s not a frown in the bunch as the whole family gathers for an outdoor portrait. Kate, William, George, and Charlotte look as happy as they can be on a gorgeous autumn day. Kate is a bit dressed down but looks elegant as usual in jeans, a crisp button-up shirt, and a cardigan.

Perfect Summer Day

Prince William must have been so proud to see his wife and son greet him at a polo match in the summer of 2015. Kate looks comfortable, but absolutely adorable, in skinny jeans paired with a striped shirt and moccasin flats. It’s a perfect look for a warm day spent outdoors.

Hiding That Baby Bump

Even though she suffered through severe morning sickness (technical term: Hyperemesis Gravidarum) with both of her pregnancies, Kate always rallied and did her duty as a public servant. Dressed in an elegant but demure navy blue ensemble, she looks radiant next to William at this event.

Here We Are!

Although we’ve seen Duchess Kate in much more casual ensembles than this, the blue dress she’s wearing for a plane ride is pretty simple. Then again, it’s a big step up from the baggy sweatpants, t-shirts, and flip-flops that a lot of us wear when we travel.

Doggone Adorable

This is quite a casual look that Kate’s wearing, but how else should she dress when she’s on doggy duty? Lupo’s owner certainly gets hands-on with her entire family… pets and children included. The Duchess looks very down-to-earth here in her jacket, denim, and wellies combo.

It’s Christening Day!

Kate’s look at Princess Charlotte’s christening was absolutely impeccable. She’s wearing a cream colored Alexander McQueen dress coat and topped things off with a gorgeous hat. Unfortunately, Prince Harry missed his niece’s big day. He was off to Africa, working as a wildlife ranger for a few months.

The Couple That Dresses Together

Awww, just look at this. The royal couple look so adorable in their matching outfits as they stroll along the coastline. They’re joined by their English Cocker Spaniel Lupo, back when he was just a little pup. Wonder who’s going to wash his paws off after this muddy walk?

Go Team!

Ever the sporting enthusiast, Duchess Kate loves to root for her favorite teams. In this case, it’s rugby. Here, she was spotted with William at the Rugby World Cup in 2015. It’s wonderful to see the adorable royals taking a date night out together every now and again!

It’s A Constant Struggle

When will Kate learn that wearing a skirt is basically an invitation for the wind to pick up and life it high into the air? Here she is at Rose Hill Primary School in Oxford wearing Irish designer Orla Kiely. It’s such a cute look but no match for the weather.

Kate’s First Love

Kate’s first boyfriend was Willem Marx. The young lovebirds met and dated while attending Marlborough College. Willem, who now resides in New York, is an Emmy-award nominated journalist. An Oxford graduate, he spent time as a reporter in Iraq.

The two have remained friends over the years. Willem attended Kate and Will’s April 29, 2011 wedding ceremony but she did not attend his nuptials when he married in 2014. Before he married Johanna Botta, he was linked romantically to model Elettra Rossellini Wiedemann and a magazine editor named Shirley Leigh Wood Oakes.

Motherhood Suits Kate

Kate is clearly a wonderful mother to George and Charlotte. She’s very involved, hands-on, and active. This can occasionally lead to some rather awkward moments, though, such as when Prince George threw a tantrum during his first official royal engagement. Here, it looks like Kate’s about to have a wardrobe malfunction as she squats to be closer to Charlotte during their visit to Canada in 2015.

Kate Goes Risqué

We’ve seen that Kate donned some rather questionable looks in her younger days, but now that she’s a mother (and a Duchess!) she tends to play it a bit safer in the fashion department. On a 2014 trip to Australia and New Zealand, Middleton stepped out in this pink number that turned quite a few heads. She looks stunning, as always, but is showing a bit more chest than we’re used to now.

What Does Green Mean?

Kate Middleton always gets a lot of attention for the stunning fashions she wears. When she appeared at the British Academy of Film and Television Arts in February 2018, however, her outfit led to more gossip than usual. Kate chose a deep green gown to wear to the event and stood out against the sea of black dresses that were worn as part of the “Time’s Up” movement.

Photo by Max Mumby/Indigo/Getty Images
Photo by Max Mumby/Indigo/Getty Images

But the dress had a black sash, leading many to theorize that she was subtly showing support of the movement, which aims to end harassment and discrimination. The royal family is not supposed to comment publicly on political issues. Heavily pregnant Kate might not have had a lot of black options for the ceremony, either.