1999, Prince

Prince, the undeniable musical virtuoso, could make the heavens sing with his talent, but even his fashion choices had moments that left us with more questions than answers. In the whirlwind of the late ’90s and the turn of the millennium, Prince embraced the futuristic fashion trend with open arms at the 1999 MTV VMAs.

He boldly paired an electric blue latex turtleneck with equally audacious tight blue pants, creating an ensemble that defied convention. Of course, this is Prince we’re talking about, and he somehow managed to rock the outfit with an unparalleled flair that only he could summon.