The Transformation Of Pippa Middleton From Childhood To 40

Philippa "Pippa" Middleton — better known simply as "Pippa" — didn't ask to be in the public spotlight, but ever since her sister Kate, now Princess of Wales, married Prince William, her life has been scrutinized almost as closely as if she were a member of the royal family. Ever since she stepped out in her famous, figure-flattering white satin gown at Kate's wedding, the public has wanted to know everything there is to know about the fabulous English woman. 

For starters — there's much more to Pippa than the "socialite" status that has been bestowed upon her. "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 previously told the Daily Mail. She's worn many hats, and not just the ones that go with her fabulous fashion choices. From her rural roots to her career and family life outside of the public eye, Pippa has plenty of substance beyond her connections to the monarchy.

Over a decade after she stole the show at her sister's wedding, Pippa has gone on to accomplish several feats. While she is constantly compared to Kate and former working royal Meghan Markle, Pippa stands out perfectly fine on her own. From obscurity to rubbing shoulders with royals, here's a look at Pippa Middleton's stunning transformation.

Pippa Middleton grew up in rural Berkshire, England, about an hour away from the hustle and bustle of Kensington Palace. She, her sister, and her younger brother James spent most of their childhood in a cottage called West View. "[We] grew up in the countryside so being outdoors and involved in sport has been a passion and in my blood," she told Hoka. 

Pippa's childhood was quite different from her peers, however, in that she got a first-hand look at living in another country when she was just a toddler. Pippa and her sister left England and spent two years in Amman, Jordan, beginning in 1984, after their father Michael relocated for his British Airways job. 

While nowhere close to royalty, Pippa's lineage provided her with a privileged life. Her great-grandmother was a member of a famous political dynasty, and her father, Michael, came from an aristocratic and wealthy Yorkshire family. Pippa's mother Carole also had money of her own, as her former company Party Pieces, which sold event decorations, took off in the late '80s.  Despite growing up wealthy, Pippa admitted certain rules still applied during her childhood. "We had to eat everything on our plate and not be fussy about food," she told the Daily Mail. "There were times when I would be sitting at the table after lunch or dinner, having not eaten something because I decided I didn't like it and actually remaining there until I had eaten it."

Pippa Middleton was privileged enough to study at some of the best schools the United Kingdom has to offer. She attended the private academy, St. Andrew's Preparatory School, when she was growing up, and was later enrolled at Marlborough College — the same secondary school that Princess Eugenie was previously enrolled in. 

Middleton went on to study English at Edinburgh University in Scotland where she received her bachelor's degree. She decided to pursue a master's degree at the University of Wales Trinity Saint David, researching physical literacy and how to encourage kids to be more active at home, according to Town & Country. Middleton completed her master's in 2022 and went on to present her graduate research findings at the fourth CIAPSE Congress in Luxembourg.

"I am passionate about sport and exercise and also love being with children," she said in her presentation in Luxembourg (via Instagram). "I wanted to find a topic that combined these two and felt that there wasn't enough information, knowledge, or focus on early years physical development for mums particularly." Middleton managed to complete her studies while being a mother to two kids and being pregnant with her third child. "I have enjoyed the balance of work and motherhood and getting back into reading, writing, and learning again," she said.

Don't let her pretty face fool you — Pippa Middleton is much more than a royal's younger sister. Middleton has accomplished many things in her life, including becoming a published author. In 2012, she announced a book deal with Penguin to write her party planning book, "Celebrate: A Year of British Festivities for Families and Friends." Middleton shared first-hand event tips that she learned from her own mother, after previously working for Carole's Party Pieces company and adding to the company's blog. Book sales weren't exactly skyrocketing, however, perhaps because the tips offered were ones like, "For Halloween, a pointy hat, fake hair, and a broom [make] a witch's outfit," and "When hosting a party, move any clutter from the space where you're entertaining."

Middleton went on to start a food column in the supermarket magazine Waitrose Kitchen in 2013, dishing on tips to help lead a healthy and active lifestyle. She also became a contributing editor of Vanity Fair in the same year and was in charge of writing several columns for the outlet. Her media presence proved to be a nuisance for her brother-in-law Prince William, however, who was reportedly wary of how it could affect the royal family. "It was felt by William in particular that she needed some guidance and support," an insider told the Daily Mail in 2016. In the years following, Pippa worked less and took a break from the spotlight.

Pippa Middleton may not have counted on being the sister to a member of the royal family — but now that she is, her life has drastically changed. Following her sister Kate's wedding to Prince William, many said the younger sister took center stage at the nuptials as she continued to make headlines in the following months. 

A lot of the commentary had to do with her backside, as her butt became the topic of conversation when she donned her figure-hugging Sarah Burton Maid of Honor gown. In the 2011 TLC special "Crazy About Pippa" (per E! News), she was even accused of adding extra padding to the backside of the dress to give herself a fuller look. In an interview with "Today" (per The Hollywood Reporter), Middleton says she was blindsided by becoming tabloid fodder. "It was completely unexpected. I think the plan was not really for it to be a significant dress," she revealed. "[It was] really just to sort of blend in with the train. I suppose it's flattering. Embarrassing, definitely. It wasn't planned."

Being Kate's sister has meant that much of Pippa's personal life has been scrutinized in the media. Her work, love life, and day-to-day activities often become headline news, and she is still trying to wrap her head around it all. "It's a bit startling to achieve global recognition (if that's the right word) before the age of thirty, on account of your sister, your brother-in-law, and your bottom," she wrote in her book, "Celebrate" (per Marie Claire). 

Pippa Middleton became an ambassador for the British Heart Foundation in 2014, working to raise awareness about heart health by encouraging physical activity and a healthy lifestyle. "I was shocked to learn that nearly three times more women die from coronary heart disease than breast cancer," she told the organization. An avid runner herself, Middleton took part in a 3,000-mile Race Across America cycling challenge as well as a 6.5km Bosphorus Cross-Continental swimming competition in Istanbul in her efforts to spread the word about heart disease and maintaining physical health.

In 2015, Middleton joined forces with UK designer Tabitha Webb to create an exclusive scarf and dress to help raise funds for the British Heart Organization. "I wanted to do something different and exciting on behalf of this inspiring charity ... [I] am thrilled I was able to collaborate with Tabitha on this project to help raise additional funds and awareness for the charity," she told Fashion Network.

Fitness has been a huge part of the mother of three's life ever since she was a child, and she was even awarded a sports scholarship to attend Marlborough College during secondary school. She became an ambassador for the running shoe brand, Hoka, and told them: "I love the simplicity of [running] — just a good pair of trainers (HOKA shoes now of course) and you're set to enjoy it anywhere in the world. No special kit or equipment, no frills nor fancy." 

Before Pippa Middleton became a married woman, she had quite a few eligible bachelors trying for her hand. While she studied at Edinburgh University and well before she was thrust into the public eye, she dated JJ Jardine Paterson, whose family is a part of a Hong Kong banking dynasty. The two reportedly dated for three years before ending their relationship amicably and remaining on good terms. Middleton then went on to date the handsome millionaire Alexander Spencer Churchill, who is a distant relative of Sir Winston Churchill and a nephew to the Duke of Marlborough. The pair reportedly met while vacationing in Mustique in 2009, and were spotted out together a few times before their romance fizzled out. 

The Edinburgh graduate was most notably seen attending her sister's wedding in 2011 alongside Alex Loudon, a former England cricketer, and Prince William's former classmate. Though the pair made quite the entrance at the nuptials, their romance ended after about seven months. Loudon reportedly wasn't too keen on the media circus that surrounded his ex-girlfriend.

Middleton found love again with stockbroker Nico Jackson, with whom she started dating in 2013. They seemed incredibly happy together on their various outings throughout their nearly three-year romance, but ultimately called it quits when Jackson had to relocate to Geneva for work. The mother of three ultimately found her prince charming in hedge fund manager James Matthew, whom she briefly dated in 2012. The two started seeing each other again in 2015 and have been together ever since. 

Pippa Middleton had her own fairytale wedding when she tied the knot with James Matthew in 2017. After going public with their relationship in 2016, Matthews popped the question later that summer with a stunning Asscher-cut diamond suspected to be worth over $263,000. 

Middleton and her beau said their vows in May of 2017 at St. Mark's Church in Englefield, England. The mother of three wore a custom Giles Deacon lace-adorned cap-sleeve gown and Manolo Blahnik pumps, paired with a Stephen Jones tulle veil. She opted for tying her hair back in an updo complete with a beautiful Maidenhair Fern tiara. Her sister Kate didn't serve as her Maid of Honor on the special day due to the delicate situation of her being a royal and the fear that she may upstage the bride, according to reports. Regardless of her title, Kate was by her sister's side on the special day to ensure it went off without a hitch. 

Prince William and Prince Harry also attended the nuptials, which were followed up by a reception at Pippa's parents' Georgian property in the town of Bucklebury. Around 300 guests filed into a giant $100,000 glass greenhouse erected on the 18-acre estate to celebrate the post-wedding festivities. "This is the wedding Pippa and James dreamed of," an insider told People. "They said all along they wanted it to be a private family wedding at home in the beautiful countryside with their closest friends and family."

Pippa Middleton and James Matthews announced they were expecting their first child in 2018, a year after she walked down the aisle to say "I do." Their son, Arthur Michael William Matthews, was born in October of that year in the Lindo Wing of St. Mary's Hospital in London — the same hospital where her sister gave birth to her children. 

Three years later, Middleton and Matthews welcomed their second child, a daughter named Grace Elizabeth Jane in March of 2021. Their first daughter's name honored her grandmothers – Carole Elizabeth Middleton and Jane Matthews. Adjusting her fitness routine to becoming a mother was a new challenge for Middleton, who told Hoka in 2021, "Running and fitness still form part of my weekly routine but not to the level it was before," adding, "My running has been more after babies and toddlers than crossing finish lines, which I'm fine with — for now!"

Grace became a big sister in June of 2022 when Pippa gave birth to her second daughter Rose. While there's no telling how Middleton came up with the name, it could be a nod to her daughter's birth flower, as roses are associated with June birthdays. Rose was christened in March of 2023 at Middleton's local Berkshire church, with Prince William and the Princess of Wales attending the ceremony.