Kelly Osbourne
Like Avril Lavigne, Kelly Osbourne had a more rebellious style than other female stars of the 2000s. As the daughter of rocker Ozzy Osbourne, she grew up with a bit of a rebellious streak and had the attitude to match. Kelly's outfits during that decade leaned towards the emo aesthetic, as seen here with her hair bow and Care Bears tutu dress.
Fans were quite surprised when Kelly Osbourne revealed her new look in 2021. Besides losing weight, it appeared that she had undergone significant cosmetic surgery.