Style & Beauty

The 1999 Grammy Awards: A Flashback To Wonderfully '90s Fashions

Women like Lauryn Hill and Madonna were the big winners that year, but all the great outfits were a close second.

On Sunday night, the music industry’s biggest stars ― minus Ariana Grande ― will attend the 61st annual Grammys. But until then, we’re going to party like it’s 1999.

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:

Will Smith and Jada Pinkett Smith
Ron Galella, Ltd. via Getty Images
Sarah McLachlan
Ron Galella, Ltd. via Getty Images
Crystal Bernard
Ron Galella, Ltd. via Getty Images
Natalie Imbruglia
Ron Galella, Ltd. via Getty Images
Jennifer Lopez
Barry King via Getty Images
René Angélil and Celine Dion
Jeff Kravitz via Getty Images
Beck
Jeff Kravitz via Getty Images
Alanis Morissette
Jeff Kravitz via Getty Images
Bono
Jeff Kravitz via Getty Images
Aaron Carter
Jeff Kravitz via Getty Images
Jennifer Love Hewitt and Ricky Martin
Jeff Kravitz via Getty Images
Big Punisher and Fat Joe
Jeff Kravitz via Getty Images
Brad Whitford, Tom Hamilton, Joey Kramer, Steven Tyler and Joe Perry of Aerosmith
Jeff Kravitz via Getty Images
Brandy and Monica
KMazur via Getty Images
Erykah Badu
Kevin.Mazur/INACTIVE via Getty Images
Emmylou Harris
Steve.Granitz/INACTIVE via Getty Images
Shirley Manson and Garbage
KMazur via Getty Images
The Dixie Chicks
Frank Trapper via Getty Images
Mya
Frank Trapper via Getty Images
Madonna and Shania Twain
Ron Wolfson via Getty Images
Tim McGraw and Faith Hill
Ron Wolfson via Getty Images
Foxy Brown
KMazur via Getty Images
Usher
KMazur via Getty Images
Brian Setzer
Steve Granitz via Getty Images
Missy Elliott
Jim Smeal via Getty Images
Trudie Styler and Sting
Frank Micelotta Archive via Getty Images
Howie Dorough, Nick Carter, AJ McLean, Kevin Richardson and Brian Littrell of the Backstreet Boys
Jim Smeal via Getty Images
Lauryn Hill
Jim Smeal via Getty Images