Although Mary J. Blige wasn’t officially a Bad Boy artist, she and Diddy’s days at Uptown Records solidified an undeniable bond. When she hit the scene in her signature look that gave tomboy vibes with a feminine edge, everyone knew she had the it-factor. Her baggy all-white ensemble paired with a bustier from the ‘Real Love’ video is unforgettable and set the tone for style wins to come.
Lil’ Kim’s arrival to the 1999 MTV Awards is not just Bad Boy history, it’s pop culture history. Known for her risqué approach to fashion, If anyone could pull this look off, it was Kim. She even got love from Diana Ross for the jaw-dropping moment. We’d say that’s a style victory for sure.
Who can forget Total’s all-Black leather ensembles from the ‘Cant you See’ video? Their looks were not only cool and sexy but quintessential 90’s attire.
As the voice of Bad Boy, Faith Evans has always been a leading lady in the game. Although she was all about rocking a chic suit in the 90’s, the star never shied away from a luxurious fur. Here, she gives us a moment in a croped fur jacket and white pants.
June Ambrose made a name for herself in the 90’s as the celebrity stylist of hip hop. The brains behind Diddy and Mase’s unforgettable shiny suits, June is a fashion icon in her own right. When it comes to her personal style, she never dissapoints with bold, in-your-face moments like this.
Laurieann Gibson (aka Boom Kack) is Diddy’s go-to for the hottest choreography in the game. Known for her boundary-pushing, all-or-nothing attitude, Laurieann’s work and style personifies the Bad Boy spirit.
