Pippa Middleton’s Most Talked-About Outfits

It’s difficult to fathom now — in a post-Kardashian era of bodycon dominance and hyper-artificial contours — to recall that Pippa Middleton’s figure, modest by any modern standard, once caused an international stir. But this was 2011, before BBL culture reshaped the beauty standard and the Instagram body replaced the real one. As she followed her sister Kate down the aisle in an ivory Alexander McQueen bridesmaid dress, it was Pippa’s silhouette that briefly eclipsed the bride.

Intended to complement the bridal train, as she confirmed in her TV interview with TODAY, the dress was unassuming by royal standards; her figure in it, apparently was not. Within days, she was crowned “Her Royal Hotness,” and a website devoted exclusively to her rear-end attracted over a million views. “I suppose it’s flattering,” she told TODAY, but she added, “I was surprised and still don’t understand it.

Kate may have had the royal wedding, and the custom Sarah Burton design for Alexander McQueen to match, but when Pippa married hedge fund manager James Matthews in 2017, it was the younger sister’s dress that sent headlines into a frenzy. Naturally, the ceremony didn’t draw the same worldwide coverage as her sister’s (which, considering the strange things in Kate Middleton and Prince William’s marriage we just can’t ignore, may have been a blessing in disguise), but the gown itself won widespread admiration from fashion bloggers and experts alike.

Made by British couturier Giles Deacon, Pippa’s gown featured a high neckline, cap sleeves, and a corseted bodice that flared into a full, sweeping skirt. The gown was overlaid with intricate lace, and completed with a cathedral-length veil and a delicate tiara (just one of the wedding accessory trends every bride should know).

The Boodles Boxing Ball, held annually in London, was one of a wonderfully quaint British fixture in the noble social calendar. Though it had its last hurrah in the summer of 2025, in its heyday, it was a black-tie charity fundraiser with all the gilded sparkle and peerage pomp. 

In 2011, Pippa Middleton stepped into the ring (metaphorically) with a look that drew many admiring glances. She wore a raunchy red Temperley London gown that truly packed a punch. Designed with a fluid, glossy fabric, the dress teased onlookers with its plunging neckline and flattering cinched waist. It was a clear left hook to the demure drapes and safe silhouettes of palace-approved fashion; this was Pippa going for the sartorial uppercut.

Temperley, a fabulous favorite of both Middleton sisters, is usually associated with a romantic, English aesthetic. This look, though, was risqué enough to secure a full-blown red carpet knockout.

If your brother-in-law’s brother is marrying your sister’s sister-in-law-to-be, what does that make you? Well, in Pippa’s case it made you a guest at Harry and Meghan’s Windsor Castle wedding. For the occasion, she wore a pale mint-green silk dress by The Fold. It featured a high neckline, long sleeves, and a pleated midi skirt, all adorned with a delicate botanical print.

The look was perfectly suitable for a spring ceremony, but it was hardly an outside-the-box way to bring florals back to life in your wardrobe. Eagle-eyed onlookers quickly noticed that the color palette and petal-patterned motif bore a curious resemblance to an Arizona Iced Tea bottle. It didn’t take long for the tweet to snowball across timelines, racking up likes and shares in no time.

Back in the ring -– or, at least, the ballroom — Pippa Middleton returned to the Boodles Boxing Ball in 2015, this time in electric blue. This offered another chance for the most famous bridesmaid in Britain to make a statement. And she did.

Wearing a halter-neck Jenny Packham gown, Pippa traded Temperley’s sultry satin for something lighter in spirit but equally engineered to steal shows. In electric blue with a crystal-clad bodice and a playful keyhole cutout, it struck a different note. If her 2011 gown was femme fatale, this was more disco debutante.

Packham, whose glittering client list spans from Dita von Teese, to Taylor Swift, to Paris Hilton (not to mention her sister Kate), is a master of feminine creations that dazzle and flatter. Her signatures — sparkle, softness, timelessness, jewel tones, and dramatic dynamism — were all on show here.

The Boodles Boxing Ball wasn’t the only time Pippa Middleton made a splash in blue that year. When she attended the 2015 Disability SnowSport UK ParaSnowBall, her plunging powder-blue gown by Hugo Boss drew plenty of attention, namely due to its deep-V cut. With this look, it seemed any lingering doubt about who the sexier sister was had officially been put to rest.