Cindy Crawford, 1992
The supermodels of the 1990s, specifically Cindy Crawford, were the best-dressed attendees of the 2019 awards show before Bella and Gigi Hadid. Who could possibly forget Versace’s leather and sheer dress?
Cindy Crawford, 1992
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TLC, 1995
It wouldn’t be a roundup of classic MTV VMA looks without mentioning the power of the girl band in matching ensembles. While matching outfits on the red carpet were all the rage in the 1990s and early 2000s, no other look is as timeless as TLC’s 1995 MTV VMAs ensemble. With baggy pants, a bare midriff, and chunky boots, this is an influential look that we still see on the gram today—and the song Waterfalls, for which they received four nominations that year, is still a classic.
TLC, 1995
