Kate Middleton's Killer Legs Couldn't Save Her From These Questionable Outfits

When it comes to royal fashion, Catherine, Princess of Wales, is a trendsetting icon. She's never been afraid to show off her sense of style, and she's often taken some real fashion risks that have paid off. Kate Middleton knows how to look good in almost anything, which is why she doesn't shy away from some seriously leggy, luxurious looks. However, with hundreds of public events and high-profile outings every year, and each of her looks getting put under a tabloid and pop culture microscope, it's not surprising that some ensembles have just come up short.

Many times, even when one of her outfits is a bit too busy or, worse yet, profoundly pedestrian and boring, she can often still make it work through the sheer force of her gorgeous gams. Sometimes, simply allowing the beautiful royal to flaunt her legs moves the needle when it comes to popular opinion and takes a dress from being a disaster to being one of her greatest underrated outfits. After all, it's been reported that Kate's killer legs are what won over Prince Harry, Duke of Sussex, when Kate first sparked her romance with William, Prince of Wales. These dresses, however, couldn't even be redeemed by Kate's stunning stems.

In May 2025, Catherine, Princess of Wales traveled out to Scotstoun, Glasgow, to participate in the christening and official naming ceremony of the anti-submarine frigate HMS Glasgow. For the special event, Kate Middleton went full yacht-club look, in a very modest, navy blue dress that went right below her knees, with white trim, and a matching wide-brimmed hat. While she gave off an appropriate nautical vibe for the occasion, it was hard not to feel the look was bland and somewhat uninspired, earning it a place among a number of Kate's looks in 2025 that completely missed the mark.

While attending an event in honor of the 80th annual VE Day event in May 2025, commemorating victory in Europe following the end of World War II, Catherine, Princess of Wales, donned yet another of the beloved polka dot ensembles that she so frequently embraces. The black-and-white polka dot dress itself wasn't the major issue with the look, and her toned legs looked stunning in the form-fitting number. The problem also wasn't the retro-style black hat with an attached veil. The true misstep was her choice of a chocolate brown handbag that clashed instantly with her otherwise entirely two-toned outfit.

In November 2022, Catherine, Princess of Wales, joined her husband, William, Prince of Wales, at a charity event in Scarborough, England, and decided to rock beige-on-beige. The underwhelming combination included a belted, knit turtleneck dress with a matching coat from Max&Co, and a DeMellier handbag. The outfit overall left much to be desired when it came to the color department, and even seemed to match her own well-tanned and toned legs. The minimalist ensemble ended up just looking boring and unfortunately bland.

There's nothing wrong with classic elegance and retro flair. However, Catherine, Princess of Wales, may have gone a bit too old-school with her look at a garden party at Buckingham Palace in May 2022. Kate Middleton looked more like the ghost of a Victorian noblewoman than a modern day royal in a mint green dress that featured a high collar and just way too many small, decorative buttons. Overall, the blast from the past vibe was made all the more bizarre by the ensemble's awkwardly puffy cuffed sleeves, ornate hat, and pleated skirt – which perhaps would have been scandalous back in the day for showing quite a lot of ankle.

Most of the polka dot dresses worn by Catherine, Princess of Wales, are beautifully organized, precisely designed masterpieces. Then, there's whatever she decided to wear to a charity event at the Stewards Academy in September 2016. Kate Middleton opted for a very busy, haphazard pattern, which included randomly placed black and white polka dots, often overlapping, across a powder blue dress. The Altuzarra design looked like it was supposed to be something fun and playful, but came off as chaotic and one of Kate's tackier outfits that many won't soon forget. Not to mention the dress' racey thigh-high slit that showed perhaps more skin than Kate intended whenever she walked with her long strides.

In April 2011, just days before tying the knot, Catherine, Princess of Wales, was spotted out and about with her then-fiancé, William, Prince of Wales, in Northwest England. The soon-to-be-royal was already famous for her striking fashion sense, but this last ensemble before becoming a princess made Kate Middleton look particularly pedestrian. The navy blue Amanda Wakeley outfit included a dark top and a skirt with an above-the-knee hemline, as well as a matching blue jacket top closed with a slew of hook and eye fasteners that feel wildly outdated even in 2011.

Shortly after getting married, Catherine, Princess of Wales, donned a butter-colored Jenny Packham dress for her first visit to Canada as a bona fide member of the royal family. Kate Middleton and her new husband, William, Prince of Wales, arrived at their destination in July 2011, and the pomp and circumstance of the moment was almost immediately ruined by some strong winds that blew Kate's dress up, leading to one of her most famous risqué moments, and one of the most notorious royal wardrobe malfunctions caught on camera.

One might think that we have a problem with Catherine, Princess of Wales, wearing so much polka dot — and that simply isn't true. She just wears an incredible number of polka dot dresses, and not all of them are going to be home runs. So, it's almost disappointing when one comes close and stumbles. This was the case with an Alessandra Rich dress Kate Middleton wore in May 2019 that revealed so much more leg than even Kate likely expected. The dress, which she wore to a D-Day commemoration event at Bletchley Park, was a buttoned-down number, but revealed a rule-breaking thigh-high slit when Kate's old nemesis, mild wind, entered the equation.