2002, Britney Spears
Britney Spears, the former pop princess, decided it was high time to shed her innocent image, and she did so with a memorable fashion choice featuring an all-leather ensemble crowned by a matching hat. In today’s fashion landscape, this outfit isn’t wild, but back then, this look was undeniably edgy — especially for Britney Spears.
While her bold style certainly stirred controversy, it wasn’t the only talking point of the night. The real spotlight moment came when she interacted with the late pop icon Michael Jackson. The king of pop appeared momentarily perplexed, momentarily mistaking her words for an award. The exchange was a memorable, slightly awkward moment in VMA history.