Kate Middleton's Leggiest Looks Before Becoming Princess Of Wales

You’d be hard-pressed to find current pictures of the Princess of Wales rocking hot pants and miniskirts — but once upon a time, she actually did sport them. Admittedly, one of her leggiest looks was for a costume party. Even so, some of the times Kate Middleton showed off her killer legs have also been surprisingly recent. 

Odds are you did a double take after reading “the Princess of Wales rocking hot pants,” so it only makes sense to start there. Back in 2008, the then-girlfriend of Prince William joined forces with friends Holly Branson and Sam Waley-Cohen to organize a charity roller disco for a children’s hospital ward named after the latter’s late brother. At the time, People reported Waley-Cohen saying of the event, “We wanted to do something fresh and new; something that would be fun and a bit tongue-in-cheek reflecting the lighter side of life.”

Max Mumby/indigo/Getty

Suffice it to say, mission accomplished. The event was full of the next generation of high society, from Holly, whose father is Sir Richard Branson, to Princess Beatrice (and naturally, Pippa Middleton was in attendance, too). However, that’s not to say there was no controversy. Royal sources speaking to the Daily Mail claimed that higher-ups at Buckingham Palace viewed Kate’s behavior at the party as a “most unladylike display.” It’s possible they were referring to Kate falling at one point in the night. The outlet had already passed some serious judgment there, lamenting, “The less than demure yellow hotpants she was wearing also did little to conceal her dignity.” Yikes. Surprising as the outfit was, there’s no question that it was hardly inappropriate for the occasion — and we’re also going to go out on a limb (geddit?) and say Kate probably didn’t plan to fall in front of the paparazzi. 

As many will know, Catherine, Princess of Wales and William, Prince of Wales broke up for a few months in early 2007. However, the future Princess of Wales seemed determined to not spend all her time moping at the apartment she and Pippa Middleton shared. Au contraire, the sisters were seen partying it up in London on a number of occasions — and for most of them, Kate opted for sleek minidresses. 

One lewk that stood out was a black mini she paired with a black blazer and peep-toe heels. The shoes being peep-toe are notable, as it was clear the newly single twentysomething had eschewed pantyhose for the night (which she didn’t even do for the roller disco). All in all, it was an unexpected choice for her. 

It’s worth noting that Kate’s approach to single life (read: looking easy-breezy and unbothered in public) has been widely reported on. In fact, in March 2025, Daily Mail columnist Richard Eden opened up about the very first time he met with her, which was just days after her little black dress moment. While at the “Young Stalin” book launch, Eden recounted that he, Kate, and royally connected Tara Palmer-Tomkinson had been chatting when the latter asked about how Kate was coping, post-split. Eden wrote that Kate had shyly but decisively shut it down, even after Palmer-Tomkinson pushed for more. “She made it clear with her body language that she didn’t wish to discuss the subject, and the conversation moved swiftly on to happier and less fraught matters,” he recalled. In case you were wondering, Kate wasn’t in a minidress that particular evening. However, it was an above-the-knee pick all the same.

As most know, Kate Middleton and Prince William’s breakup was short-lived, and by July 2007, numerous reports emerged suggesting they were back together. Countless outlets also pointed to both of them singing along to “Back for Good” at the July 1 Concert for Diana as evidence that they were officially back on. Granted, they were seated away from one another (though still in the same box), but it was thought that that may have been to avoid too much attention. Even so, Kate’s outfit for the concert didn’t slip under the radar. 

While coat dresses are generally seen as the now-Princess of Wales’ go-to for more formal occasions, her white coat dress for the concert has us thinking she probably loved these long before becoming a member of the royal family. That said, even though some of her coat dresses have shown off her killer legs, there’s no question that her pre-royal white trench-style piece was significantly shorter than anything she’d wear today. 

In addition to a black handbag and minimal silver jewelry, Kate finished off the look with a pair of black boots that hit below the knee. She also seemed to have ditched the tights for the day. All in all, a very chic ensemble. 

Whether or not the Concert for Diana marked Prince William and Kate Middleton being back together for good (feel free to hum the song in their honor), a few years later, they were officially married at Westminster Abbey. After that, they headed off on their honeymoon — though not without a quick photocall. 

For their departure from Buckingham Palace, Kate wore a periwinkle minidress topped with a black blazer and a pair of black wedges. It was a stunning look for the new Duchess of Cambridge, and classic enough that years down the line, it’s continued to hold its appeal. Further than that, though, it also emphasized just how long her legs are. For reference, Kate is pretty tall, coming in at 5-foot-8. 

One detail that outlets didn’t fail to recognize at the time was the fact that the dress was from Zara. In fact, more than a decade later, Express lauded Kate once again for the affordable pick, which had set her back just £49.99 (or just under $65). The publication also pointed out that just as Kate has recycled other inexpensive dresses in the past, she wore the dress again for a royal engagement in 2016. While the dress wasn’t the main focal point of her later look (she was wearing a buttoned-up coat over it), sure enough, it was clear in some shots that it was the same one she’d worn for her honeymoon photocall several years prior. Yas for re-wears!

Just over a month after her wedding, the then-Duchess of Cambridge made a public appearance in a skirt that was surprisingly even shorter than the dress she’d left for her honeymoon in. Though she followed the same approach of a floaty minidress topped with a jacket when she attended the Epson Derby, this time it was all white, creating an ethereal vibe. 

Perhaps because of the new royal rules she had to follow, Kate Middleton wore nude tights for the outing. However, far from making her look frumpy, the sheen of the tights made her legs look even longer, and so flawless they appeared almost Barbie-esque. In addition to the tights, the newlywed also wore a pair of nude stiletto pumps, which created the illusion of much longer pins. Oh, and one extra detail added to her height — the duchess donned a nude fascinator, too. 

Truth be told, we’re a little sad the now-Princess of Wales hasn’t recycled this particular look, because she looked sensational. Having said that, it’s possible she had it in mind when she began wearing Self-Portrait’s blazer dresses with chiffon pleated skirts, which she owns a number of. Granted, those have been a little longer, but we guess Kate’s new title of Princess of Wales requires a touch more formality. 

Though we’re big fans of Kate Middleton’s mini moment at the 2011 Epsom Derby, even that is no match for the Gucci minidress she rocked for the unveiling of a new gallery at the Victoria & Albert Museum in 2017. 

One of her most unexpected looks of all time, the short-sleeved tweed dress featured red and black detailing, along with pearl buttons. The duchess paired it with black block heels, a red clutch bag, and pearl earrings. In a word (or two words, anyway), it was chef’s kiss. Unsurprisingly, many were shocked by the majorly different look, and some even questioned if it was the shortest dress she’d worn since becoming a royal. Her Epsom Derby dress was a little shorter, so that isn’t the case. However, the stronger lines certainly do qualify it as one of her boldest picks during her time as the Duchess of Cambridge. 

While many have noticed that Kate’s look has changed dramatically in her time since becoming the Princess of Wales, perhaps her Gucci dress will be one of her re-wears in the coming years. If not, here’s hoping she’s kept it in her closet for Princess Charlotte to try once she reaches her teens.