Join us on a digital trip back 20 years, when some of the biggest music stars of the ’90s stepped out for the 41st annual Grammy Awards at the Shrine Auditorium in Los Angeles.
It was, of course, 1999, and women dominated the nominations. Every singer competing in the Album of the Year category was a woman, and Lauryn Hill came out on top. Hill took home five awards that night, Madonna won four and Celine Dion and Shania Twain each won two.
The women may have been the real winners of the night, but all the wonderfully ’90s fashions that appeared on the red carpet were a close second. Will Smith wore a full leather (or perhaps pleather?) suit, Crystal Bernard looked like she arrived straight from a Renaissance fair, and Brandy and Monica put their boyfriend rivalry behind them to sport color-coordinated ensembles. It was a time.
Below, check out all those outfits and more: