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11. Katy Perry 2008
Katy Perry attended her first VMAs in 2008. Back then, the singer was always stepping out for events in vintage-inspired getups, and it was no different at the VMAs. She opted for a white satin corset top and feathered hot pants, along with metallic fuchsia pumps and a glittering clutch in patriotic colors.

For her hairstyle, Katy chose a voluminous curly hairstyle complete with a bedazzled clip. And to finish off the look, she swept on some red lipstick that amped up the retro vibe.