Roy was raised in Northern California by an Indian father and Dutch mother and grew up in a strict Seventh-day Adventist household. She landed her big break, both professionally and personally, when she met rap mogul Damon Dash at a Madison Square Garden boxing match in 1998. After the two began dating, Dash hired her to work on the Rocawear clothing line he'd co-founded, and she soon became creative director. In 2005, Dash cut ties with Rocawear and sold his stake to partner Jay-Z. Roy left, too, founding a clothing line of her own, with financing from Dash. Although Roy's line quickly won praise from critics and fashionistas, it was the couple's shared social connections (and her exotic beauty) rather than her design skills that ensured a flood of press and a long line of celebrity followers.
Roy and Dash had their first child, Ava, in 2001 and tied the knot in a quickie ceremony in 2005, reportedly because Roy was incensed to learn that Dash had fathered a child with another woman the year before. Roy gave birth to the couple's second child, Tallulah, in the middle of 2008, but they split up by the end of the year. [Image via Getty]