Jessica Stam
A popular model and the inspiration behind a very expensive Marc Jacobs handbag, Stam is also known for her romantic escapades with skanky men.
Canadian-born Stam grew up in a devout Christian family before being spotted at age 14 in a Tim Horton's. Two years later she was a working model living on her own in the U.S., and caught the eye of Steven Meisel, who photographed her in his campaigns for Versace and Prada. She soon became one of the most popular models, and her "fragile" look, contrasted with her coal-rimmed eyes and ever-changing hair color, has earned her a cult-like following among fashionistas. She's appeared in ad campaigns for L'Oreal Paris, DKNY, Lanvin, and BCBG and walked the runway for the likes of Marc Jacobs, Anna Sui, Zac Posen, and Victoria's Secret. Designer Marc Jacobs liked her so much he named a purse after her: the $1,600 "Stam" bag sold out almost immediately.
Like most models, though, Stam has noteworthy extracurriculars. She took a stab at acting in the short film Agent Orange and also fancies herself a designer with small collections with Rag & Bone and Rachel Roy. For a while Stam was involved with Red Hot Chili Peppers frontman Anthony Kiedis, who is more than two decades her senior. She's also dated Malcolm Ford, the son of Harrison Ford, New York Rangers star Aaron Voros, and the late Adam Goldstein (that's DJ AM to you who don't remember the mid-aughts). [Image via Getty]