The Most Shocking Outfits Pippa Middleton Has Ever Worn

When Prince William and Kate Middleton announced their engagement on November 16, 2010, the media coverage was all but inescapable — as the world beheld the soon-to-be Duchess of Cambridge's dazzling smile, her dark flowing locks, and that breathtaking royal blue Issa dress that spawned what's known as the "Kate Effect."

Enter Kate's little sister, Pippa Middleton, or should we say, Pippa Middleton's behind. On Kate's big day — which garnered an estimated 23 million American viewers — one image stands above the rest: Pippa and her shapely bottom, as she carried the train of her sister's wedding dress up the stairs of Westminster Abbey. Though Kate typified the intrinsic elegance of a princess, it was her sister — that is, her sister's rear end — that was all the rage. As Ingrid Seward, editor of Majesty magazine, told The New York Times in 2013, "Pippa did not just steal the limelight at her sister's wedding. She was the limelight."

The columnist and author has since tried to keep a low profile, focusing much of her attention on being a wife and mother of two. But, alas, she has become the obsession of British paparazzi. While much of the internet lauds her sense of style, she hasn't escaped online vitriol. In 2013, Liz Jones of the Daily Mail wrote, "There is one thing poor Pippa Middleton does not have, and unfortunately for her it is something money can't buy: style." Ouch!

From see-through dresses to outfits that had us seeing double, here are Pippa Middleton's most shocking looks.

The derriere seen round the world

It was the bodacious bottom that made Pippa Middleton the world's most famous maid of honor. Dressed in a curve-hugging Alexander McQueen bridesmaid gown, she managed to upstage her royal sister at her own wedding. That's quite a feat! So besotted were people with her sheathed derriere that she was given the sobriquet "Her Royal Hotness" and even landed on People's list of the "Biggest Body Moments" of 2011.

Middleton was also a boon to the plastic surgery industry, causing a spike in surgical butt lifts that year, per ABC News. "In that wedding gown, she created a stir," Miami plastic surgeon Dr. Constantino Mendieta told "Good Morning America" in 2011. "People want those dimensions. She's just gorgeous." Mendieta said on the show that, after the royal wedding aired, demand for butt lifts at his practice grew exponentially, with a considerable portion of women hoping to attain Middleton's pert posterior.

While Middleton admitted to Matt Lauer on the "Today" show that the unexpected fame from her backside was "embarrassing," she at least seemed to have a sense of humor about it. In 2014, speaking at a dinner for Women in Advertising and Communications, she publicly addressed the ballyhoo over her rump, joking, "In retrospect [the dress] fitted a little too well" (per The Mirror). She added, "As I have found out, recognition has its upside, its downside and — you may say — its backside."

Pippa Middleton's black see-through dress turned heads at London's Sugarplum Ball

Freezing temperatures didn't stop Pippa Middleton from showing off her svelte figure in a sheer dress at London's Sugarplum Ball in November 2013. Paired with a sequined jacket and purple chandelier earrings, the black-embroidered, art deco-style gown was a head-turner that night. Middleton topped off her look with a coiffed updo, simple makeup, and a swoosh of her signature black eyeliner. Referring to Middleton's ensemble, Marie Claire published the headline "Pippa Middleton Breaks All the Royal Rules in Sexy Sheer Dress." If royal women are expected to dress according to the proprieties of British high society, then Middleton is something of an outlier.

One could only imagine the frenzy if Middleton's ultra-famous sister, Kate, wore such a gown to a formal event. The royals have a laundry list of strict dress codes to follow — women's dress hemlines shouldn't be above the knee, for example — and Kate, unfortunately, has had her fair share of fashion missteps. Even though Pippa Middleton is an ostensible royal, and thus doesn't have to follow the same protocols as her sister, that hasn't absolved her from public scrutiny. It's not surprising, then, why she was both the belle of the ball and the talk of the town at the Sugarplum Ball that year.

She jumped on the sheer-dress bandwagon again at Wimbledon in 2017

If there's one place where Pippa Middleton feels right at home in public, it's Wimbledon. The famous royal-in-law has been spotted dozens of times at the sporting event, sometimes playing it safe in a white flutter-sleeve sundress — white is the preferred dress code at Wimbledon — or playing it up for the cameras in a short, form-fitting floral dress. The paparazzi had a field day when Middleton had a near wardrobe malfunction at the semi-finals in 2019. Wearing a yellow, sunflower-printed wrap dress by Ganni, Middleton recovered gracefully as a gust of wind threatened to blow up the high slit of her dress (via Cosmopolitan). That didn't stop photographers from getting a great shot of Middleton's incredibly toned thigh, however.

What could be more attention-grabbing than that? How about a see-through dress — in broad daylight! On Day 3 of the 2017 Wimbledon Championships, Middleton caused quite a stir in a pastel pink lace Self-Portrait dress, so transparent that she reportedly needed "an underskirt and sheer top panel to cover up," noted InStyle. This was a bold and sexy style choice for Middleton, who typically opts for a more conservative look to the event. Perhaps the then-newlywed was still enjoying those honeymoon vibes.

Wearing the same dress as your sister in public: fashion faux pas or sweet?

If your big sis is a duchess and a worldwide fashion icon, why wouldn't you want to follow in her footsteps? Indeed, Pippa and Kate Middleton have had some serious twinning moments. At Princess Charlotte's christening in July 2015, onlookers had to do a double take to determine whether they were looking at Kate, Charlotte's mother, or Pippa. Kate wore a cream-colored Alexander McQueen dress paired with a matching fascinator by Jane Taylor and nude pumps. Pippa looked nearly indistinguishable from her sister in a dress and hat of the same style and color. The only dead giveaway: She wasn't pushing a baby stroller.

This wasn't the first or the last time Pippa and Kate have given us déjà vu. Once, the sisters were photographed wearing not just similar outfits, but the exact same dress, merely one week apart. Talk about keeping us on our toes! In October 2018, Pippa was spotted on the streets of London with her newborn son, clad in a burgundy polka dot dress complemented with a chunky scarf, white sneakers, and trendy round shades. One week earlier, at the Teen Heroes reception, Kate donned the same Whistles dress, embellished with Cassandra Goad gold earrings and heels. 

While the two have long shared a close relationship — Pippa waxed affectionately about her sister in a 2014 interview with "Today" — their look-alike moments bring new meaning to the term "sisterly bond."

Bringing nude pantyhose back in style

One of Pippa Middleton's biggest fashion blunders wasn't for doing something wrong, but, rather, for doing something right, at least by Queen Elizabeth's standards. The look in question evokes an ongoing predicament among women: to wear pantyhose or not to wear pantyhose? The decades-old fashion accessory is both seductively stylish and, especially in cold weather or professional settings, reliably practical. Love or hate nude stockings, the queen is apparently a fan, and we're sure this was one fashion choice Middleton made that pleased her. Royal expert Victoria Arbiter explained to Insider in 2017, "You never see a royal without their nude stockings." She added, "I would say that's really the only hard, steadfast rule in terms of what the queen requires."

In 2012, at one of the promotional events for her first book, "Celebrate: A Year of Festivities for Families and Friends," Middleton looked classy and chic in a tweed Stella McCartney dress, her legs accentuated by what appeared to be nude stockings and bold black pumps. While countless famous women have donned nude pantyhose over the years, one thing is certain: When Pippa Middleton covers her gams in sheer nylon, people respond. The Telegraph reported that sales for nude pantyhose increased by up to 85% in 2011, thanks to the stylish Middleton sisters, both of whom were spotted on several occasions that year allegedly sporting flesh-colored legwear.

Some folks, however, were not happy with the trend. In 2011, Jezebel posted the headline "Fashion Icon Pippa Middleton Commits Ultimate Pantyhose Sin," while Tracey Lomrantz Lester with Glamour wrote, "I confess, I'm something of a nude hosiery hater myself — I can't help but be reminded of Hooters and elderly church-going ladies when I see tan pantyhose." Point taken.

Pippa Middleton seems to steal the spotlight at other people's weddings

Pippa Middleton is frequently spotted at weddings. Her wedding-attire collection includes everything from the V-neckline raspberry number she wore to Camilla Hook and Sam Holland's nuptials (a design reminiscent of sister Kate's engagement dress) to the stunning cornflower blue Kate Spade dress she wore to the royal wedding of Lady Gabriella Windsor and Thomas Kingston. Then there was that maid-of-honor dress (you know the one!). 

As much as she seems to enjoy attending weddings, she also, without fail, steals the spotlight at them. Her ensembles often impress and dazzle. Some of her wedding-guest outfits sell out in a frenzy — the Kate Spade dress nearly sold out in less than a week, according to Glamour UK — with consumers clamoring to replicate her look. Yes, the Pippa Effect is just as real as the Kate Effect.

Some outfits, however, have not been so well received. In 2013, while attending the nuptials of Lady Melissa Percy and Thomas van Straubenzee, Middleton wore a fitted black-and-white peplum dress by Tabitha Webb and a jaunty pillbox-style fascinator. Black stiletto pumps and a matching clutch completed the look, as noted by Marie Claire. However, Charlie Anderson, who reportedly once styled Princess Beatrice, was not impressed. Speaking to The Daily Beast, she said, "This black and white wedding outfit is not bad, but it still manages to miss the mark. Is it the matchy-matchy accessories? Or just the lack of a modern, flattering cut that does it?" Love or hate her style, Pippa Middleton knows how to create a stir!

She isn't turning heads with just her backside

Pippa Middleton proved she has curves when she arrived at the Boodles Boxing Ball in 2011. Wearing a jaw-dropping red Temperley dress with a plunging neckline, Middleton may have beat out every other woman at the ball in the cleavage department, including former Spice Girl Geri Halliwell, who also donned a similar low-cut red dress. As noted by HuffPost, the ball was a charity event to raise money for the Starlight Children's Foundation and the Lt. Dougie Dalzell MC Memorial Trust, which was set up to help wounded servicemen and their families, as well as pay tribute to Dougie Dalzell, a British officer who was killed in Afghanistan.

The good news was that the event raised a lot of money — a table cost £1,950, or roughly $2,500, per The Mirror — but the bad news was that all eyes were on Middleton. The Daily Mail noted that she made a splash at the event with her attention-grabbing dress. However, Liz Jones, a style director with the outlet, said, "The dress is completely inappropriate," adding, "I hate cleavage at the best of times, and Pippa cannot now really object to any comments about her shape or hounding by the press as this dress says, Look at me!"

Pippa Middleton can't seem to escape the spotlight. But with a dress like this, what does she expect?

Her dress to Meghan Markle's wedding was mocked as looking like a can of Arizona Green Tea

At Prince Harry and Meghan Markle's wedding, Pippa Middleton found herself caught in another media spectacle, except this time it wasn't for her sexy attire but, rather, for looking like an Arizona iced tea beverage. Middleton, who was then pregnant with her first child, arrived at the event with her husband, James Matthews, wearing a mint green floral dress by The Fold that featured a high neckline and long sleeves. Completing the look, Middleton sported nude heels and a light-pink fascinator by Jess Collett paired with a matching clutch.

The look was conservative yet stylish, mature yet playful. But that didn't stop the online fashion police from poking fun at her expense. Twitter was abuzz with cheeky comments and memes comparing the dress to a can of Arizona Green Tea (per Time). The company itself even engaged in some lighthearted joshing, writing on Twitter, "Pippa got you feelin' thirsty?! Stop by the Great Buy 99 Pop-Up for a free can of the real thing!" (per The Sun).

At least everyone's attention was on her dress this time instead of her derriere.

Pippa Middleton wore a racy dress to a Parisian costume party

Women clad in cleavage-baring period costumes, men in periwigs and spiked leather collars, an almost naked nun — does it get more scandalous than that? It does if a royal adjacent like Pippa Middleton is partaking in the fun. In April 2012, Middleton attended a decadent birthday party for her friend, fashion designer Vicomte Arthur de Soultrait. Guests were decked out in what looked like 18th-century costumes, but with a more salacious flair. There were even burlesque strippers at the event. And, unfortunately for Middleton, there was also the paparazzi, eager to snap racy photos of the Duchess of Cambridge's little sister.

Perhaps the most damning photo taken, published by the Daily Mail, was of de Soultrait sitting on a mock throne, flanked by Middleton and another woman wearing a low-cut, sky-blue gown, as someone from out of the frame pulls on the chain attached to de Soultrait's dog collar. Though Middleton's outfit — a period-themed pink-and-gold dress paired with a biker jacket and lace-trimmed capris leggings — was modest compared with those of other guests, she still received heated backlash for attending the event. 

Buckingham Palace did not release a public statement in response to the photos, reported CBS News. Max Clifford, a well-known British PR figure, said (per Los Angeles Daily News), "It's very damaging for her, it's a totally irresponsible, stupid thing to do. ... The last thing the royals need is someone like this."

But who hasn't let loose and done something they regret? Middleton was only 28 at the time, after all.

Making a bold statement at Wimbledon in 2016

Pippa Middleton channeled her inner retro chic when she attended the 2016 Wimbledon Championships for the second time that year, wearing a geometric shift dress by Tabitha Webb, one of her go-to designers (per Hola!). This was by far Middleton's boldest look to the popular tennis tournament, as she usually opts for outfits in romantic floral print, sweet neutral tones, or classic black and white. 

The eye-catching orange-and-blue ensemble, completed with a sky-blue clutch and gray suede pumps, would have been a statement dress to any event, but at Wimbledon it was practically verboten. Adding to the transgression, Middleton sat in the Royal Box during that tournament. Dress codes are much stricter for the Royal Box, where spectators are encouraged to don a more formal, event-appropriate outfit, according to the Evening Standard. The Sun also advises that women should wear a modest dress to the event, while men should opt for a jacket and tie. If Middleton was looking to turn heads — and raise a few eyebrows — she succeeded!

Pippa Middleton wore another super sexy dress to a charity event

Like her sister, Kate, Pippa Middleton is a big supporter of charities. Unlike her sister, however, Middleton doesn't have to adhere to a strict royal dress code that demands women look professional, demure, and polished in public at all times. While Middleton's looks lean more conservative, she has occasionally taken advantage of not having dress protocols to follow. Shockingly, some of her sexiest, most daring looks have been at charity events. So long as it's for a good cause, who says you can't boast your best assets!

Looking every bit the fashion icon she is, Middleton arrived at the 2015 Boodles Boxing Ball in London to support The Gordon Ramsay Foundation. Fresh off a 47-mile swim-run competition in Sweden, the then-32-year-old sashayed into the event, wearing a bright blue Jenny Packham gown, which featured a halter neck and a cutout that showed a hint of skin below her bust. The look was even more eye-catching with Middleton's sculpted post-race arms. 

The problem? Wearing such revealing dresses, especially to formal public events, could have contributed to Middleton's reputation of being a "socialite" and "party girl," two monikers she's grown to resent. In a 2016 interview with the Daily Mail, she explained, "People see me as someone privileged who has used my position to advantage; that I don't really work, that I am a socialite — that word really irritates me — and that I'm a party girl without any substance." She added, "I work very hard. I'm true to my values. I just try to live a normal life like many of my friends."

Was Pippa Middleton a bad luck charm at these weddings?

Let's be honest, if there's one place where superstitions are allowed — and often followed — it's at a wedding. While the "something old, something new, something borrowed, and something blue" tradition is well known, as is the rule that only the bride should wear white, some may be unaware that wearing green to a wedding is thought to be bad luck. That is if you're following Irish folklore, which claims that wearing green, especially to weddings, attracts fairies (per Bustle). And these are not the cute Disney fairies, but the kind that bring chaos to those who dare to displease them (via The New Daily).

We guess Pippa Middleton didn't get the memo! In 2017, she wore a teal knee-length dress adorned with a large embroidered flower to the nuptials of longtime friend Camilla Campion-Awwad and Oliver Jenkinson. She finished off her outfit with a black floral fascinator and gray high heels (via People). Romantic and elegant, the ensemble won the praise of fashion experts. But green to a wedding in Ireland? Surely the fairies were ready to bedevil the poor bride. In fact, according to National Geographic, green, despite its popular associations with St. Patrick's Day, is generally considered an unlucky color among the Irish. Tsk, tsk, Pippa Middleton.

She made the same mistake again in 2018 when she arrived at Princess Eugenie's royal wedding and wore a dark green Emilia Wickstead dress with a matching Jane Taylor London hat. We'll forgive her, however, since she was nine months pregnant and rocking four-inch heels, as Elle noted.

She showed some serious cleavage at the ParaSnowBall in 2015

Not to be outdone by her past cleavage-baring dresses, Pippa Middleton wowed in another deep V-neck gown, this one designed by Hugo Boss, when she attended the inaugural ParaSnowBall in 2015. Her makeup and hair were kept simple, and the pastel blue hue of her dress was made even more stark by her sun-kissed bronze skin. She looked at once like a demure Hollywood starlet and a voluptuous '50s bombshell, à la Sophia Loren.

Though many outlets praised the look, they also commented on how flashy and revealing it was. Still, Middleton was there to support a good cause: to raise money for Disability Snowsport UK, which helps people with disabilities participate in winter sports. In her speech at the event, Middleton noted (per the Daily Mail), "As a keen skier myself, I feel very passionately about enabling those with a disability to experience the joy of skiing alongside able-bodied people."

In February 2019, four months after the birth of her son, Middleton attended a different charity event, the British Heart Foundation's Beating Hearts Ball, marking her first public appearance since becoming a new mom (via Cosmopolitan UK). She turned heads in an almost matronly floor-length gown featuring a multicolored design and a high neckline with a large black bow in the front. Suffice it to say, this look made a completely different statement from her 2015 Hugo Boss gown. Whether she's showing off her curvaceous and well-toned physique or her more conservative and reserved side, this royal-in-law is a showstopper wherever she goes.