2002, Kelly Osbourne

Embracing the vibrant graphic tee trend of the early 2000s, Kelly wore a shirt that said, “My Boyfriend Is Out of Town.” But that was just the beginning of her fashion statement. She took things up a notch with a crimped bob hairstyle, daring yellow eyeshadow to perfectly match her tee, and striking red lips that echoed the shirt’s bold hue.

However, Kelly Osbourne is far more than just a fashion icon. She’s a true triple-threat entertainer with a repertoire that includes singing, modeling, and even fashion designing. Beyond her edgy style, Osbourne is renowned for her engaging and thought-provoking contributions to talk shows and reality television.