Pippa Middleton's Most Scandalous Skin-Baring Outfits

Kate Middleton and her younger sister, Pippa Middleton, have a similarly demure fashion sense. However, certain outfits that Pippa has worn out and about over the years showed significantly more skin than the royal-family-approved ensembles that the Princess of Wales typically dons. One example is the above photo from a 2011 charity event, the Boodles Boxing Ball, where Pippa donned a bright red dress with a deep neckline. The Temperley London floor-length gown was made of silk or a similarly slinky material. In addition to the low neck, a bustle of flowers on the waistband accentuated Pippa's figure. 

The back of the dress also boasted cutouts formed by a fashion-forward X-shape crossover of the straps. Naturally, though, not everyone was thrilled with the look. As Liz Jones, style director for the Daily Mail, argued, "The dress is completely inappropriate, with no support." Jones felt it wasn't designed well for cleavage, noting, "You see the problem is this dress looked great on the catwalk, but the model was flat chested. The look doesn't translate as yet again a designer hasn't made a dress with a real woman (no matter she has connections) or real social occasions." Despite these critiques, Pippa rocked the look.

At the 2015 Boodles Boxing Ball event, Pippa Middleton stunned in an electric blue, flowing gown designed by Jenny Packham. Some of Catherine, Princess of Wales' most expensive outfits have notably been from Packham's collections, so it seems like she is a favorite designer of the Middleton sisters. Pippa's 2015 dress had halter-style straps, showing off her arms and shoulders. It also featured a small triangular cutout on the bodice. 

Pippa wore her hair down and lightly curled for the event, but the styling of the back of the dress could fortunately still be seen. Similar to her Boodles Boxing Ball dress from 2011, the straps looked to cross over each other and formed another cutout. These stylish additions may have been even more eye-catching than the sparkling flowers on the bodice of the dress. Needless to say, Pippa looked absolutely radiant in the bright outfit.

Another clear standout among the most shocking outfits Pippa Middleton has ever worn was the dress she chose for the third day of the iconic Wimbledon tennis tournament in 2017. She was photographed watching a match with her brother, James Middleton, and the ankle-length frock that Pippa donned for the festivities was from the Self-Portrait brand. It was made of pink lace and featured a white collar and eye-catching black belt.

The flowing short sleeves were sheer, so Pippa's shoulders were visible. The intricate floral embellishments comprising the lace for the rest of the dress were sewn together somewhat loosely, causing skin from Pippa's midriff, knees, and lower legs to show through the dress as well. The dress was a little revealing but still relatively tame, comparatively speaking. 

However, it was still a fashion risk, especially for someone with such close ties to an institution as formal as the British royal family. Thankfully, the risk paid off, and it's no doubt that the stylish look should land Pippa on a roster of Wimbledon's best dressed stars.