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

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Vince Bucci via Getty Images

Monica and Brandy at the 41st annual Grammys in 1999. 

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





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