The Most Unqueenly Outfits Kate Middleton Has Ever Worn

As the wife of William, Prince of Wales, it's only a matter of time before Catherine, Princess of Wales, ascends into queenhood — and there's quite a few signs that she's ready for the role. While Kate Middleton certainly loves to wear (and re-wear) some truly gorgeous royal looks, she's also rocked a whole slew of styles that were decidedly not queen-like. Famously, she's turned the heat up with some of her leggiest looks, and she's also brought a modern sensibility to the table with some fantastic pantsuit styles, all of which seem to fly in the face of most people's preconceptions of the royal family.

Looking back over her years of fame and time in the media spotlight, there's no denying that Middleton's style has dramatically changed over the years. During her college days, her go-to outfits were far from the regal regalia you see her rocking today. She even got surprisingly racy in a sheer look for a charity fashion show years before tying the knot and becoming a bona fide princess. Even recently, though, she's proven that she doesn't need to dress down to shake off the confines of aristocratic fashion expectations. Instead, she's subverted royal trends to flawlessly pull off some remarkably modern, chic, and still unqueenly ensembles.

Several years before she tied the knot with William, Prince of Wales, Kate was already putting her fame as the prince's girlfriend to good use by participating in and promoting charity fundraisers and events. One such event, held in September 2008, was a day-glo roller disco party that raised over $200,000 for a children's hospital. Almost as importantly, however, the special occasion provided Middleton an opportunity to rock an emerald green halter top covered in retro-sequins and a pair of neon yellow short-shorts while rolling around in some pink skates. It's said that Middleton had a real party girl past, and it's easier to imagine when seeing her in this ensemble.

While this long-sleeved black-and-white wrap-dress is by no means salacious or inappropriate, it's hard to imagine a queen, or even future queen, rocking something with such a busy pattern — or low-cut neckline. Catherine, Princess of Wales, wore this modern static-patterned dress during a 2013 visit to a residential treatment center operated by Action on Addiction, an organization Kate Middleton has been a vocal supporter of for many years. Middleton showed just how progressive and forward-thinking she truly is both in her actions and in her stylish and contemporary raiment.

Back in 2002, Catherine, Princess of Wales, got her chance to live out her supermodel dreams for a night by walking a runway in a racy, see-through lace dress. The catwalk moment came as part of a charity fashion show while she was a student at St. Andrews University in Scotland. Reportedly, Prince William, who became friends with Kate the previous year, was in the front row, and got the chance to see the future Princess of Wales show off her fit physique in a sheer dress, revealing her black undergarments. You have to admit, the tight, spiral-curl 'do really accentuated her carefree ensemble.

Catherine, Princess of Wales, has always been a fit and active woman who prioritizes wellness and health. Back in 2007, she showed off her impressively toned physique in some activewear — including skin-tight athletic pants and a black sleeveless top — while training with the Sisterhood Cross Channel rowing team. It's great that she chose practicality over propriety, but the royal family would likely never sport something like this. When this photo was snapped, Kate Middleton and her fellow teammates were training on the River Thames and preparing for a race against the English Channel. Middleton held her own as a top contributor on a team of very accomplished athletes as she embraced her passion for physical competition.

In March 2015, Catherine, Princess of Wales, then pregnant with her second child, stepped out for a visit to the Turner Contemporary art museum in Margate, England. The expectant mom stunned in her chic and stylish maternity gown, which featured a playful animal print fabric. It was hardly notable by common standards, but a bit outside of the wheelhouse of the typical House of Windsor. The future princess was met with a crowd of cheering fans, and she delighted them by posing with them and taking photos, all while showing off her growing baby bump. Kate Middleton's fashion sense and her humble, gracious personality gave her a very down-to-earth vibe that has long been missing from the hallowed halls and practiced distance of the royal family of England's past.

While Queen Elizabeth II never shied away from wearing some bright pink ensembles, Catherine, Princess of Wales, knows how to bring a whole new updated professional look to the delicately beautiful hue. Kate Middleton showed off her decidedly contemporary, Barbie-influenced fashion sense in a pink Alexander McQueen suit in May 2023, during a visit to London's Foundling Museum. Middleton paired the pastel pantsuit with a pearl-encrusted white belt that was the flawless flourish needed to really bring the whole ensemble to the next level. The princess was still repping an iconic English designer in Alexander McQueen, but the aesthetic was so modern that it didn't look very monarchical. 

Back in 2005, when Catherine, Princess of Wales, was attending the University of St. Andrews and was still just Kate Middleton, she wasn't afraid of showing off her casual side. Middleton certainly knew how to pull off the look of a normal college student, as seen in this snapshot showing the future princess rocking a white tank top and flashing her midriff in low-rise denim jeans. It's hard to imagine the Princess of Wales walking around in a combo like this these days, even in the privacy of her own sprawling royal estate.