The man behind the eponymous fashion line that rose to dazzling prominence in the '90s, Rodriguez sold a controlling interest in his company to Liz Claiborne in 2007, but quickly bought it back.

Rodriguez's Cuban parents hoped their son would become a doctor or lawyer, but much to their disappointment, he headed off to study fashion at Parsons instead. After graduating in 1985, he took a job as Donna Karan's assistant at Anne Klein; he later became an assistant womenswear designer at Calvin Klein, where he became close to Carolyn Bessette, who worked in the company's PR department. When Bessette got engaged to John F. Kennedy Jr. a few years later, she asked Rodriguez to design the wedding gown. His creation—a simple, sexy white silk column—ended up garnering him the sort of publicity most designers can only fantasize about. By the time the dress was splashed in magazines all over the world, Rodriguez soon decided to focus his full attention on his eponymous clothing line. His clothes made their way to the racks at Bergdorf Goodman and Neiman Marcus, and he earned the CFDA award for best womenswear designer an unprecedented two years in a row in 2002 and 2003.

But while he was basking in the glow of fawning fashion editors and adoring celebrity fans, things were decidedly bumpier on the financial front. The difficulty keeping afloat led him to sell a 50% stake in his company to Liz Claiborne in 2007, partially because (some believe) he did not pursue major expansions into accessories and cheaper lines like Marc Jacobs and Michael Kors. However, Rodriguez had a quick turn around and was able to buy back controlling stake in his company just in time for Michele Obama to wear one of his frocks to her first appearance as a FLOTUS. [Image via Getty]