Pippa Middleton's Killer Legs Couldn't Save These Bad Outfits

Pippa Middleton, sister of Catherine, Princess of Wales, has always been a bit of a gym rat. Her love for working out and staying active has enabled the British socialite to achieve some incredible accomplishments, such her completion of a 3,000-mile charity bike ride and becoming an Althlete Ambassador for the athletic wear brand HOKA. 

Taking part in triathlons and fitness challenges for years, she has always flaunted a pretty shredded physique. Most notable are Middleton's incredibly toned legs, which may in part be due to her love of running. "Through maturity, like us all, I have been faced with different hurdles and challenges, but with running as part of my routine, this has been my escapism," she wrote of her love of the exercise for HOKA in 2021. 

With such killer gams, it's no surprise that Middleton would enjoy flaunting them from time to time. Pippa Middleton has donned some shocking looks over the years, but these outfits take the cake for the most truly questionable style decisions she's ever made. As much as she has a clear love for parading her legs around London, her wardrobe mishaps have often overshadowed her impressive stems.

Believe it or not, this disastrous ensemble was for a wedding in February 2011. There was no redeeming this outfit from Pippa Middleton; even the flaunting of her legs couldn't take attention away from the ruffled mess of her jacket or the pink flowery chaos of her hat. 

Adding to the terrible tiered skirt of the black jacket was a questionable mini ruffle outline that traced her torso and bust on the top of the piece. It wouldn't be a Middleton outfit without the strangest selection of accessories, in this case a worn leather clutch and a pink flowered hat that looked like a costume piece. 

Admittedly, 2011 was a rough year for Pippa Middleton in terms of fashion, as she frequently wore ensembles that left even the British socialite's biggest fans cringing. Despite Middleton's killer legs in an outfit from September of that year, the dress was totally wrong for the Princess of Wales' sister. 

The incredibly drab neutral hues clashed with one another, and the milky color of the peach dress did not work with her natural palette. Pairing such a light and flowy piece with a highly structured leather jacket and an oversized brown bag made for a difficult meshing of aesthetics.

Pippa Middleton flaunted her muscles in a leggy look from July 2011. Her geometric wrap dress was overly complicated and poorly paired with a cropped leather jacket, which featured a dated, quilted effect along the front. 

The mix of a laptop bag and a regular purse created a bogged-down appearance to what should have been a light summer fit. Middleton's overall ensemble gave the impression that she was carrying luggage rather than strutting her stuff on a London sidewalk. 

Making an appearance at London Fashion Week in September 2011, Pippa Middleton wore a sunburst-like black and gold patterned dress styled with a black suede ankle boot and clutch. The pattern of the dress combined a jarring set of colors, especially with the tea-stained gold fabric that was clearly not in her color wheel. 

A hue to make her stunning tan skin pop would've been a better choice for such a high-end event, as well as some more polished accessories. The black ankle boots didn't reflect the high-profile runway show the outfit was intended for. 

Another outfit from Pippa Middleton's horrible fashion year in October 2011 made her look a bit dowdy. While the black color of the dress was a great choice for her, complementing her warm tan and rich hair color perfectly, the overall vibe just wasn't working.

The lace overlay that poked out along the hem of the dress cheapened the outfit and gave a frumpy aesthetic for the youthful, fit Middleton. Her accessories took away from a great base yet again, with gaudy gold flats and a gargantuan beaded bag that would have stolen the show if not for her incredibly toned legs. 

Pippa Middleton walked through the streets of New York in September 2012 in a short sleeve red dress with matching red shoes. The style was boring, a plain flop from the typically more fashion-adventurous British socialite, and didn't match the aesthetic of her woven purse. 

The design of the dress was simple and, in turn, uninteresting. Its gold button details on Middleton's shoulder and awkward sleeve length gave the piece an overall frumpy design. The flats completed the bland ensemble, but at least drew attention to the real wow factor: Middleton's killer toned legs. 

In May 2013, Pippa Middleton was photographed in a horrendous strapless mini with a slouchy blazer. The blazer made Middleton appear as though she was standing with a perpetual slump, giving her upper body no structure. 

The awkward length of the dress (between a midi and a mini) might have been better executed with a simpler pattern instead of its busy print. However, the decision to add the large belt made sense, as it broke up the print and cinched the socialite's waist. Still, the belt she picked appeared cheap with its silver buckle.

While on the arm of Pippa Middleton's then-boyfriend Nico Jackson, she wore a semi-see-through piece for the November 2013 Sugarplum Ball. The sheer skirt allowed a glimpse at Middleton's legs in a seemingly last-minute addition to the dress.  

The black sequined cropped blazer was a nightmare; it was a loud yet dowdy accessory to an already busy dress. But it's the dress that raised the most questions about the socialite's style. With a crocheted pattern on the bodice and skirt, the frock's eerie similarity to a doily could not be denied. 

On her way to Wimbledon in July 2016, Pippa Middleton stepped out in a dizzying dress with a mock turtleneck and accessories that were a bit too matchy-matchy. The dress itself was an eyesore with its jigsaw-like chopped chevron print that did little to accentuate her figure. 

Middleton's toned thighs did shine through, flaunting her fit figure with a subtle peek-a-boo. Unfortunately, they couldn't save the fit from total disaster. The outfit would have benefitted from a jacket or a belt to break up the pattern and to ease its bold print. 

It's possible that a January 2017 outfit from Pippa Middleton was meant to resemble that of a dark academic, but instead it was giving detective. The socialite's black leather gloves combined with her brown trench coat and fedora made for an almost comical appearance, crafting a look fit for a cop procedural. 

Middleton's daringly short skirt was a breath of fresh air, however, for the socialite's wardrobe that had fallen a little stale. The small flex of her strong legs did bring some youthful vibes to a borderline frumpy ensemble, but overall, the fit was just not it.