Of All Pippa Middleton's Outfits, This Is The Most Scandalous

Pippa Middleton might not be royalty herself, but her wardrobe choices have long fascinated royal watchers. Yet one gown in particular turned heads like never before, making it one of her boldest and most talked about looks to date — and it's not the infamous bridesmaid dress that you might be thinking of.

In case you've forgotten, as the younger sister of Kate Middleton, Pippa was a British socialite in the 2010s, though relatively unknown outside the UK. That all changed during Kate and Prince William's royal wedding in 2011. Pippa served as a maid of honor and wore a simple yet elegant ivory gown (by Alexander McQueen) that was stitched to perfection and showcased her beautiful figure. Her look caused quite a stir, captivating royal fans across the world. Some fans and media even claimed that her dress rivaled the bride's wedding gown (via ABC News). Reflecting on the viral moment, Pippa later shared that "it was completely unexpected," adding how "the plan was not really for it to be a significant dress" (via Today). 

Since then, she has made a series of fashion statements, but none were as scandalous as the outfit she wore to The Boodles Boxing Ball later that same year.

In October 2011, Pippa Middleton and her then-boyfriend, Alex Louden, attended London's exclusive Boodles Boxing Ball. The charity event is famous for drawing British high society and even members of the royal circle. With "Pippa Mania" in full force, Middleton made headlines yet again with an outfit far bolder than her usual elegant style. She wore a striking red satin gown (by Temperley London) with a plunging neckline that perfectly accentuated her figure. Accessorized with a golden clutch, matching heels, and subtle earrings, Middleton's look struck the balance between daring and refined.

Unlike the elegant maid of honor dress that thrust her into the media spotlight, the red gown showcased a different side of Middleton. The deep neckline and vibrant red hue stood out against the typically conservative fashion norms associated with royal circles. For some, like Daily Mail's Style Director Liz Jones, the gown's low-cut design was too inappropriate for a prominent figure so closely connected to the royal family.

At the time, Middleton and Louden's relationship was reportedly on the rocks. But her appearance at the charity event with him, dressed to the nines, put those rumors to bed. According to Hello! Magazine, "the pair were spotted kissing passionately at 4.30 am following the Boodles Boxing Ball." While some may have criticized Middleton's gown choice, it showcased her willingness to step out of the royal shadow and embrace the spotlight.