15. Bad Boy
Years Active: 1993-Present
Key Members: Diddy, Ma$e, The Notorious B.I.G., Craig Mack, The LOX, Black Rob, Shyne, G-Dep, Faith Evans, Total, 112, French Montana
Elements of Style: White suits, Shiny suits, Sweatsuits, Lumberjack shirts with matching hats, Coogi sweaters, Versace, Moschino
Sean Combs always had an eye for style, back when he was making Mary J. Blige and Jodeci look fresh in their videos. Bad Boy style circa 1993 revolved around Puff Daddy and The Notorious B.I.G. from the Timberlands and Coogi sweaters, to Don-worthy suits and Versace shades. Paul Hunter's unforgettable "Hypnotize" video had every dressed-up rapper in the game wanting a speedboat. In 1997, Bad Boy ushered in the era of the shiny suit thanks to the "Mo' Money, Mo' Problems" video and stylist June Ambrose.
A year later came the launch of the Sean John line, pushing the whole sweatsuit thing to a new level before expanding into a full-fledged fashion brand. Currently, Sean John does revenues of over $132 million. Yeah, in addition to the vodka money he's making, it's safe to say Ciroc Obama can keep throwing those all-white everything parties for a while. Recent Bad Boy artist French Montana is known for his love of Versace gear, and you know what? He looks great in it.