If longevity is the game, then Stephanie Seymour is winning. The San Diego native has lived at least two fashion lifetimes: First we loved her as the rebellious supermodel, and now as the sophisticated woman with timeless sex appeal. Born on July 23, 1968, Stephanie started her career at age 14 with small local assignments. A year later she won Elite's Model Look contest and bigger things were soon to follow.

The much-loved Sports Illustrated swimsuit model landed on her first Vogue cover, shot by Richard Avedon, in 1988. Stephanie went on to work with other esteemed photographers, including Herb Ritts, who photographed her iconic British Vogue cover. Soon fronting campaigns for Almay and Dior, Stephanie helped usher in the age of the supermodel in the good company of Cindy, Linda, Naomi, and Claudia. Then, in 1992, the star signed with an unknown lingerie company called Victoria's Secret. Seymour helped put the brand on the map, and in doing so, became synonymous with lingerie. Now, at 40, she represents Chantelle, a French lingerie company. 

Stephanie's life has been as hot off camera as on. She dated Guns N' Roses frontman Axl Rose and starred in the band's famed videos "Don't Cry" and "November Rain." Their very public and volatile relationship ended with mutual lawsuits in 1993. A year later, Stephanie met media mogul Peter Brant. The pair married in 1995 and has three children together: Peter Jr., Harry, and Lilly. Stephanie has another son, Dylan Thomas Andrews, from her first marriage to guitarist Tommy Andrews. 

As a wife and mother in Greenwich, Connecticut, Stephanie's life may have quieted a bit, but her career has never slowed down. In 1998, while the face of L'Oréal, she released her book, Beauty Secrets for Dummies. She even dabbled in Hollywood with a role in the Oscar-nominated film "Pollock."

Although she never really stepped away from the spotlight, Stephanie made a refreshing appearance in Marc Jacobs' quirky ads in 2001. And she continues to awe the fashion world today, as evidenced by her racy runway appearance as a sexy nurse in the Louis Vuitton show and spectacular editorial in Pop's 2008 Spring issue (they nearly dedicated the entire issue to her). Clearly the timeless head-turner is as relevant as ever. In fact, she kinda makes you want to be 40.