The Most Outdated Outfits Pippa Middleton Has Ever Worn

Pippa Middleton — technically Pippa Middleton Matthews these days — has spent a lot of time in the public eye since her sister, Kate Middleton, married Prince William of Wales and became the Duchess of Cambridge. As such, we've all paid witness to Pippa's incredible style transformation over the years, but the journey hasn't all been smooth sailing. Compared to other figures in and around the British royal family, Pippa tends to jump on trends and statement pieces rather than stick to timeless fashions, and this has sometimes landed her in sartorial trouble.

As fashion consultant Sandra Ellis once told The Daily Beast, "Overall, Pippa needs a stylist that can help her choose pieces that work with her sensibility and body shape and not what is current or fashionable. Pippa appears to be a rather traditional girl and trying to make her look cool simply doesn't work." Adding insult to injury, many of those "current" fashions have since fallen by the wayside, leaving Pippa with a veritable photo album of out-of-style paparazzi shots. Flipping through them feels a little like peeking into our own high school yearbooks — did we really think that looked good? At least our own embarrassing pictures can be stowed away in the attic or quietly deleted from social media. When it comes to Pippa's most outdated ensembles, we have too much evidence to ever forget.

Pippa Middleton has had some stunning style moments, but at Tatler's 300th anniversary party in 2009, both her taste and her dress seemed cheap. The one-shouldered silhouette, flamenco-like ruffles, and jarring boldness of wearing a black belt against butter-yellow fabric all felt straight out of the 1980s — or, worse, the early-noughties club scene. Imagine trying to repurpose the bridesmaid's dress of your worst nightmares by accenting it with somewhat edgy accessories, and this is what you'd get. No, Pippa. Just no.

Strolling the streets of New York City in 2012, Pippa Middleton was a little too quintessential in her 2010s fashion. Not only were her era-defining colored skinny jeans eye-searingly orange, but their cut was so high that they were bordering on capris. There's a reason that many millennials have been dreading the recent capri resurgence — twee pedal-pushers have already come in and out of style more than enough times, and if even Pippa can't pull them off, maybe it's time to let them die out for good.

At another event in 2012, Pippa Middleton elected to wear a high-waisted metallic skirt that looked unbearably stiff in retrospect. The bronze fabric's thick, jagged waistband missed artsy and landed on tortured. Adding thick, black tights and fawn-colored shoes didn't provide any cohesion, creating a mishmash of unmatched neutrals with no clear focal point. Relative to some other missteps, this look was inoffensive and probably could have been saved with different styling. But worn as-is, it was a discordant blend of 2010s fashion concepts that wouldn't make the cut today.

Vivid hues had a moment in the early 2010s, but we're going out on a limb to guess that Pippa Middleton's blue, feathered frock was anachronistic even then. The boxy silhouette and fluffy lower half looked more 1923 than 2013, and it wasn't even an elegant throwback. The color harmony between the peach and navy trim had potential, but all subtlety was lost against the cobalt-blue base. Ultimately, this look didn't work as an homage or a reimagining. Instead, it came across as a cheap rehashing of antiquated styles.

A few years ago, you couldn't move without tripping over pleated maxi skirts in sweet, floaty fabrics like silk and chiffon, but we still can't love the gown Pippa Middleton wore to the 2013 Boodles Boxing Ball. Even ignoring the Halloween-y black-and-orange color scheme, the dress design left much to be desired. Its chunky, cross-halter neckline overemphasized Pippa's shoulders, the awkwardly placed waistline lengthened neither her torso nor her legs, and the maxi skirt completely swallowed her. It was a big swing but also a big miss.

Was 2013-era Pippa Middleton okay? Playing with trends is one thing, but she really pushed out the boat with the fluttery bohemian trousers she donned for a night out that September. First, there was the cartoony pattern, which relied on a busy mess of motifs. Then, there was the befuddling palette of black, beige, and magenta — not exactly a classic color combo. And while we usually believe you can style blazers for any season or occasion, Pippa's boring jacket had no chance of creating a timeless look with these pants.

Pippa Middleton has hopefully left her worst fashion years behind her, but there's still the occasional misfire. For instance, we weren't fans of her Wimbledon 2024 ensemble. The pink print was passé, the ribbon belt was too youthful, and the flouncy capelet neckline felt more matronly than modern. Altogether, this ensemble made us think of "Harry Potter" bureaucrat Dolores Umbridge. Chopping off a foot or two might have helped balance the hyper-feminine details, as a midi length would inject much-needed flirtiness into the stodgy look.