Most stylish moment: Anytime he was seen with J. Lo

Bad Boy went for the threepeat in 1999, when Diddy emerged as a superstar in his own right with his official solo debut Forever (1997's No Way Out was billed to "Puff Daddy & the Family"). For the first time, after a decade-plus ruled by casual streetwear, Diddy made it OK for rappers to wear high-end suits half the time. He cashed in on his growing status as a style icon by launching Sean John the year prior; it eventually became one of the most profitable, respected urban fashion lines of all time. To top it all off, back then he was sporting the flyest accessory of all: J. Lo on his arm.

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