2000, Pink
Pink has never been one to follow the crowd, whether it’s in her music or her fashion choices. In a style mashup that left heads spinning, Pink paired a sequined halter top with pants that seemed to defy gravity (seriously, how did they stay up?).

Adding to the spectacle, she sported a bold, spiky pink hairdo that looked like it could pierce the heavens and a coat that, while fashionable, raised ethical eyebrows about its source. While we love her fearless approach to music and her fashion, this particular look might have us reaching for something a bit less, well, avant-garde.