Scandalous Outfits We Can't Believe Pippa Middleton Wore

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Pippa Middleton first became a household name thanks to the dress she wore to her sister and Prince William's wedding, but when it comes to her wardrobe, for the most part, she tends to stick to more conservative looks. Even so, there have been a few occasions where she's opted to spice things up — and, at least by royal standards, her choices could be considered downright scandalous.

First things first, her bridesmaid dress. Now, while there were plenty who felt Pippa was somehow in the wrong for her well-fitted white dress, we certainly don't fit into that category. After all, there's no question Kate Middleton (and possibly even royal aides) weighed in on the look. In fact, since Kate was the bride, there's a good chance that the now-Princess of Wales chose the look. 

Either way, there's no denying the dress brought a ton of attention to Pippa — and speaking of the dress and the attention it received on "Today," she revealed that the ensuing public obsession had been hard on her, particularly because she hadn't really anticipated it. "I think the plan was not really for it to be a significant dress. Really just to sort of blend in with the train," she explained. Of course, the dress ended up becoming much more than that, and the future Lady of Glen Affric has also seen the funny side of that. As she joked in her speech at the 2014 Women in Advertising and Communications dinner, "Recognition has its upside, its downside and — you may say — its backside" (via Mirror). 

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Pippa Middleton might not have wanted to attract attention at her older sister's royal wedding, but we doubt that was the case when she picked a dress for her appearance at the 2011 Boodles Boxing Ball. For the occasion, Pippa donned a spectacular yet simple fire engine red silk dress with a deeply plunging neckline. The dress also featured a massive floral detail just under the bust. In short, we wouldn't be surprised to see this lewk on an actor at the Cannes Film Festival or even on a Bond girl. 

In fairness to Pippa, aside from the plunging neckline, the dress wasn't overly revealing. In fact, the neckline wasn't all that different from some of the outfits Kate Middleton wore prior to marrying Prince William. With that in mind, even though the dress would be a no-no by royal standards, since Pippa doesn't have a royal title, she was and is free to dress however she'd like. 

Our take? Pippa looked sensational for the charity bash. What's more, since Boodles Charitable Trust describes the event as a glamorous, star-studded one, there can be no question that the future queen consort's younger sister looked the part.

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From one movie star-esque moment to the next, in 2015, Pippa Middleton opted once again for a plunging neckline. This time, she rocked a light blue Hugo Boss number for her appearance at a disability SnowSport UK fundraiser — and again, she looked incredible.

Though there were some similarities between Pippa's 2015 dress and the one she'd worn to the Boodles Boxing Ball several years prior, it does seem as though the later iteration showed slightly less skin. The neckline, though plunging, was certainly a little more narrow. Plus, the fabric also went a long way in taking the dress from va-va-voom to somewhat more demure. As with the red dress, Pippa also kept additional skin-bearing to a minimum. Of course, this look still wouldn't have got a royal stamp of approval — but then again, Kate Middleton's sister need hardly have worried about that. 

As an aside, Pippa gets major snaps for picking the perfect dress for the theme yet again. The icy color of her dress was the perfect pick for a snow sports fundraiser. Pippa's picks might not be royal family-appropriate, but she's certainly a lot like her older sister when it comes to nailing the art of literal dressing. 

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Back to the Boodles Boxing Ball (say that three times fast), in 2015 Pippa Middleton returned to the event with another daring lewk. This time, she did so in a bright blue dress — and though there was no cleavage, there was plenty of skin. In addition to a low halter-neck, the dress also had a cut-out between the bust and waist. What's more, the dress also had a high-low skirt (remember those?) which put Pippa's killer legs on display. 

All in all, it was probably Pippa's most daring look to date. However, as with her other looks, it was still hardly the most revealing dress. Are we expecting to see Kate Middleton borrow it any time soon? Absolutely not. However, it does bear mentioning that the dress she wore to promote Eurovision 2023 did bear striking similarities to Pippa's pick, so perhaps the Princess of Wales found a way to try it, albeit in a more royally appropriate way. 

At the end of the day, most of Pippa's lewks over the years have leaned more modest, even when considered scandalous by royal standards. We're not likely to see her go much more daring than a low neckline and a cut-out, and it's almost always going to be balanced out with a longer skirt. Oh, and there's a very good chance it'll be perfectly on theme, too.