Rumors About Pippa Middleton That Will Always Haunt Her

The younger sister of Catherine, Princess of Wales, may not be a royal, but Pippa Middleton lives a really lavish life. After studying English literature at the University of Edinburgh, she worked at a public relations firm, then became an event planner, and topped it all off by publishing a party planning book in 2012 dubbed "Celebrate: A Year of British Festivities for Families and Friends." Initially, it seemed like an on-brand move — after all, her mother, Carole Middleton, founded a party supply company called Party Pieces — but the book wasn't much to celebrate. Per The Guardian, the tome was quickly ridiculed by reviewers for lacking substance and featuring arguably uninspired tips, including but not limited to: "For Halloween, a pointy hat, fake hair and a broom [make] a witch's outfit." As Pippa herself later told the Daily Mail in 2016, "Maybe it might have been better if I had waited a bit longer before doing it." Not that she let the flub (which earned her an advance of £400,000) get her down.

That same year, Pippa became engaged to financier James Matthews whose fortune is believed to be in the billions. After a million-dollar wedding, they moved into a multimillion-dollar mansion and continue to enjoy the finest things in life. Even so, Pippa insists that looks can be deceiving. "People see me as someone privileged who has used my position to advantage; that I don't really work, that I am a socialite," she told the Daily Mail. "That word really irritates me." And yet, critics aren't buying it, as Pippa hasn't been able to escape talk about her alleged social climbing and sneaky attempts to outshine her sister, among other things. Here are the biggest rumors about Pippa Middleton that continue to follow her.

Long before she was Catherine, Princess of Wales, Kate Middleton was thought to be something of a social climber. Some critics even claimed she switched schools, swapping the University of Edinburgh for St Andrews at the last moment, just so she could cross paths with Prince William. Shortly after, younger sister Pippa Middleton started her own college career at the University of Edinburgh and while she never dated a royal, it didn't stop folks from painting her with the same brush. Indeed, The Scotsman noted in 2008 that Catherine and Pippa had collectively been dubbed the "Wisteria Sisters," a nod to the wisteria plant, which is known for its ability to grow vertically and climb up walls.

According to insiders who spoke with The Scotsman, Pippa was very much interested in climbing Britain's social ladder and so, she used her time at the University of Edinburgh to connect with the right people. "She was very charming about it, but quite ruthless in cultivating the 'right' friends," a source told the outlet. "If she found out that someone had impressive social credentials — the right title, standing, connections — she would immediately pay them a lot of attention." And it wasn't just outsiders who believed Catherine and Pippa had ulterior motives in the friends they chose. According to royals expert Katie Nicholl, the sisters' middle-class upbringing even led to name-calling among Prince William's university friends who reportedly referred to the family as the "en masse Middletons," per Express.

Long before both were happily married, Prince Harry and Pippa Middleton sparked romance rumors that lasted for several years. As a source alleged to OK! Magazine, "sparks flew" between them at the 2011 wedding of Prince William and Catherine, Princess of Wales. So much so that the source claimed, "Kate went to check her makeup and found them snoggin in the bathroom!" Shortly after, Harry shut down the rumors, telling curious VIP guests at London's Hard Rock Calling concert, per the Daily Mail, "Pippa? Ha! No, I am not seeing anyone at the moment, I'm 100 per cent single."

Even so, OK! Magazine ran another story about the pair in 2015, claiming they were bonding over the birth of Princess Charlotte, then went so far as to declare they were having a full-on secret romance. "They're trying to play it coy, but there's no doubt that this is developing into something serious," the aforementioned source claimed to OK! Magazine. "They're truly sweet together and, in fact, seem very much in love."

Interestingly, Harry filed an official complaint with the Independent Press Standards Organisation (IPSO) after those very quotes were printed in various British tabloids. The ruling went in his favor, concluding the stories about him and the younger Middleton sister dating were misleading and not based in fact, resulting in them being retracted in the U.K.

When Pippa Middleton said "I do" to billionaire James Matthews in 2017, it was a lavish affair worthy of a royal couple. However, it seems the bride ruffled the feathers of an actual royal on her big day as it's been claimed that Pippa's demands for her lavish wedding really upset Prince Harry and Meghan Markle. At the time, Harry and the "Suits" actor had only been dating for about 10 months and, according to insiders, all the attention they were receiving made Pippa uncomfortable. "The media frenzy that followed their every move made them somewhat of a reluctant addition to the guest list," authors Omid Scobie and Carolyn Durand wrote in their 2020 book, "Finding Freedom," per Us Weekly. "Both the bride and her mom, Carole, privately harbored concerns that the American actress's presence alongside Harry might overshadow the main event."

Ultimately, Markle didn't attend the church service, but she did show up at the reception which was held at Bucklebury Manor, the estate owned by Pippa's parents, Michael and Carole Middleton. Even so, it seems the new couple was in for another harsh surprise, as they weren't seated together for dinner. Instead, Harry sat with British news reporter Tom Bradby while Markle shared her table with Roger Federer's wife, Mirka Federer, per the Daily Mail. It needs to be said, however, that the move was not a personal snub, as all couples were separated for the reception.

While she's often been called down-to-earth by the press, it seems Pippa Middleton's neighbors are convinced she's actually a diva. As of 2022, Middleton and her husband, James Matthews, have called the 145-acre Barton Court estate home. The £15 million (about $19.7 million) property previously belonged to British designer Sir Terence Conran who was apparently very open with his land. According to the Daily Mail, Middleton and her hubby turned much of the village against them in October 2024 when they decided to block a footpath that had previously been accessible to everyone. Described as a country lane, it was a popular walking spot, although it admittedly led to the home's private driveway. Ultimately, the couple decided to hang up multiple signs declaring it to be private property and while some understood the decision, others were left fuming. "I have been walking along there for 50 years," one local told the outlet. "These people seem to be overprotective of their property," another slammed. "With all the notices stuck up, it feels like us and them."

Middleton and her family again faced backlash from their neighbors while celebrating Matthews' 50th birthday in September 2025. According to the Daily Mail, the party Middleton threw her husband was a major disruption to locals who claimed music was blaring until 1:30 a.m., not to mention the noisy military flyby from Spitfire planes. "I thought this might happen when Pippa moved in — people with money," seethed one local.

The 2011 wedding of Kate Middleton and Prince William was a royal event for the ages, however, it was younger sister Pippa Middleton who became the talk of the town. Indeed, various outlets accused Pippa of stealing the spotlight from Catherine, Princess of Wales. Not only was her dress white but the perfect, curve-hugging tailoring soon went viral for being almost too sexy. Notably, photos of Pippa's backside as she carried the train of Catherine's dress took the world by storm. Within days, a Facebook fanpage entitled "Pippa Middleton A** Appreciation Society" had over 200K followers. Pippa kept mum on the matter until 2014 when she explained the moment was unintentional and that the notoriety was not what she had hoped for. "As I have found out, recognition has its upside, its downside and — you may say — its backside," she quipped at the Women in Advertising and Communications dinner, per Page Six.

Even so, she was again accused of trying to outshine Catherine's dress just a few years later. During Princess Charlotte's christening in 2015, Pippa showed up in a cream-colored dress, hat, and heels that were nearly identical to Catherine's. Etiquette expert William Hanson told Daily Mail that Pippa may very well have been trying to court the media's attention because she could have easily checked in with Catherine about her outfit beforehand. "Maybe they did discuss it and Pippa decided to stick two fingers to courtesy and try once again to upstage the Duchess of Cambridge," Hanson mused. "Perhaps [she was] scared of the limelight being elsewhere."

We may never know the full truth about Kate Middleton and Pippa Middleton's relationship, but the sisters sure do seem close. They lived together after college and have been photographed at countless events together, but numerous sources believe there's a hidden rivalry between the pair. Back in 2008, a family friend claimed that Catherine, Princess of Wales, harbored negative feelings towards her younger sister for being more popular. "Kate was always quite jealous of Pippa," the insider alleged, per The Scotsman. "I sensed that she feared being eclipsed by her, because Pippa has more natural effervescence."

Those same rumors have followed the Middleton sisters for over a decade, as Pippa has been accused of outshining her sister during important occasions. Adding fuel to the fire, Catherine actually missed the 2025 birthday party of one of Pippa's daughters, Grace, to uphold a royal engagement. However, some sources believe that had nothing to do with a hidden rivalry, but rather, time management. "The unfortunate collateral of that has been losing the laid-back Middleton family way of things she holds so dear, especially her once incredibly close relationship with her little sister," a source told New Idea, noting how Cathrine has had to take on more official duties in preparation for eventually becoming Queen Catherine. Another source agreed, assuring, "There has been no falling out between Kate and Pippa."