Diddy
Before he was Puff Daddy and P. Diddy, Diddy and then Swag (just for a second), he was christened Sean John Combs. And when the Grammy-winning hop-hop mogul started his own clothing line, he went back to the basics. In 1998, Combs launched Sean John Inc., which includes men's shirts, jackets and pants. But Combs didn't stop with just his own label and fashion line. In 2004, he invested in couture label Zac Posen, and in 2008, Combs hired Dawn Robertson from Old Navy to run the company. Then Combs bought Enyce from Liz Claiborne. Combs, who rarely does anything in a small way, launched a men's perfume label called "I Am King" complete with a giant billboard in Times Square. If the ability to buy his namesake thousands of stores across the U.S. didn't keep Combs in the spotlight, ruling over Times Square had to do the trick.