4. P.Diddy, Sean John

P.Diddy, Sean John

P.Diddy's clothing line, Sean John, was founded in 1998. Maybe it won’t be the most in style any more, but it was at one point the coolest thing to wear. Not only can the singer say he has been one of the most successful rappers of our time, he can also say he has had an insanely successful fashion line. In 2004, sales figures hit $250 million for the year!

Victoria Beckham, Victoria Beckham Collection
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