Michael and Carole Middleton welcome their second daughter, Philippa Charlotte Middleton, whom they simply call Pippa. Through their mail-order party company, Party Pieces, the Middletons become self-made millionaires and move the family (which now includes brother James) to the genteel village of Bucklebury, England.
While Kate goes public with her relationship with Prince William at St. Andrews, Pippa heads to Edinburgh University, where she spends much of her time with high-society peers. She rooms with the sons of the Duke of Roxburghe and the Duke of Northumberland, and becomes romantically involved with Hong Kong banking heir Jonathan "JJ" Jardine Paterson. In 2007, "Perfect Pippa" (as she is called by pals) graduates with a degree in literature.
A single and ambitious Pippa strikes out on her own in London, first working as a publicist and later landing a job at event planning company Table Talk. Though the press hounds Kate, UK high society magazine Tatler takes notice of the younger Middleton, naming her "Top Society Singleton" of 2008. "Pippa has a reputation as being the really fun one, slightly louder and more outgoing than Kate," says former Tatler editor Catherine Ostler. "Possibly slightly naughtier."
Life for the Middletons changes forever when Kate accepts William's proposal. "As you know, Catherine and Prince William have been going out for quite a number of years, which is great for us because we have got to know William very well," dad Michael tells reporters of his family's excitement over the royal engagement. "We wish them every happiness for the future."
The royal family announces Pippa as Kate's maid of honor for her April nuptials. Pippa takes an active role in helping her big sis plan her royal wedding, and notably, planning her bachelorette party and reception, for which she reportedly requests disco balls.
Pippa makes a head-turning entrance into London's Westminster Abbey for her sister's royal wedding, carrying Kate's train in an ivory sheath designed by Sarah Burton of Alexander McQueen. Twenty-two million U.S. viewers are stunned by the 27-year-old maid of honor – and her now-famous backside. "It says a lot about how close they are," stylist and friend Nikki Pennie told PEOPLE, "that, at the wedding, Kate let Pippa have her moment, too."
Though Pippa returns to daily life working part-time for Party Pieces, she continues to be a worldwide phenomenon (dubbed "The Pippa Effect") with all eyes on her style, sportiness, and demeanor. "She's a girl who's not frightened to be seen," says royals author Alisande Healy Orme.
After her split from Loudon, Pippa spends some time with George Percy, an old roommate from her college days, with whom she exhibits PDA in London. "George is very smitten and completely in love with her," a source close to Pippa says, though the romance eventually fizzles.
In her new party-planning book, Celebrate: A Year of Festivities for Family and Friends, Middleton speaks out about dealing with life in the spotlight since her star-making turn at her sister Kate's 2011 nuptials to Prince William. "It's a bit startling to achieve global recognition before the age of 30 on account of your sister, your brother-in-law and your bottom," she writes.
BIOGRAPHY (top to bottom): The Middleton Family/AP; GEtty; Steve Finn/Splash News Online; George Pimentel/WireImage; Can Nguyen/LFI; Alastair Grant/AP; Pacific Coast News; Bauer Griffin; Courtesy: Viking