The 27 Most Unforgettable Grammys Fashions Ever, Ranked!

From the sublime to the ridiculous.

All eyes will be glued to the Grammy Awards this weekend, when a Who’s Who of the recording industry takes the stage.

We all want to know who will win, but more importantly we want to know what they’ll be wearing! Even when an outfit is a flop—sometimes especially then—it can become an iconic image for the ages.

Below, we rank the 27 most iconic Grammy looks—the good, the bad, and the ugly.


  1. Jane Fonda at the 2015 Grammys

    The 57th Annual GRAMMY Awards - Arrivals

    The 77-year-old Oscar winner wasn’t nominated for anything, but she still snatched the crown on the red carpet, in a stunning emerald Balmain jumpsuit, accessorized with a bold gold fringe necklace.

  2. Destiny’s Child at the 2001 Grammys

    43rd Annual Grammy Awards

    The House of Deréon for your nerves.

  3. Cher at the 1974 Grammys

    Cher At The Grammys

    Before there was J-Lo, Cher showed us how little you can get away with wearing on a network awards show. And that butterfly pin in her hair? #Everything.

  4. Traci Bingham at the 2001 Grammys

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    We’re not sure what this Baywatch babe was doing at the Grammy Awards, but she sure put it out there.

  5. Cyndi Lauper at the 1984 Grammys

    The 26th Annual GRAMMY Awards

    She’s so unusual—and we wouldn’t have her any other way.

  6. Lady Gaga at the 2016 Grammys

    LOS ANGELES, CA - FEBRUARY 15: Singer Lady Gaga attends The 58th GRAMMY Awards at Staples Center on February 15, 2016 in Los Angeles, California. (Photo by Larry Busacca/Getty Images for NARAS)
    Larry Busacca/Getty Images for NARAS

    Mother Monster glams it up for her epic—and emotional—David Bowie tribute performance.

  7. Annie Lennox at the 1995 Grammys

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    It’s Eurythmics meets Minnie Mouse and we love every second of it.

  8. Barbra Streisand at the 1978 Grammys

    The 19th Annual GRAMMY Awards

    Hey, it was the ’70s.

  9. Cee Lo Green at the 2011 Grammys

    LOS ANGELES, CA - FEBRUARY 13: Singers Cee Lo Green (L) and Gwyneth Paltrow perform onstage during The 53rd Annual GRAMMY Awards held at Staples Center on February 13, 2011 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
    Kevin Winter/Getty Images

    His colorful costume looked right at home onstage as he sang with a bunch of Muppets—and Gwyneth Paltrow.

  10. Nicki Minaj at the 2012 Grammys

    54th Annual GRAMMY Awards - Arrivals

    We’re calling this one “Little Red Riding Hood meets the Pope.”

  11. Whitney Houston at the 1986 Grammys

    The 28th Annual GRAMMY Awards

    Whitney looked effervescent at her first Grammy Awards—and the trophy makes the perfect accessory to her simple but elegant gown.

  12. Britney Spears at the 2000 Grammys

    The 42nd Annual GRAMMY Awards

    Hard to believe this demure 18-year-old is our Bri-Bri. They grow up so soon.

  13. Pharrell Williams at the 2014 Grammys

    56th GRAMMY Awards - Red Carpet

    What’s he hiding under that hat—more Grammys?

  14. Lady Gaga at the 2011 Grammys

    56th GRAMMY Awards - Red Carpet

    We suddenly have a craving for eggs.

  15. Lil’ Kim at the 1998 Grammys

    The 40th Annual GRAMMY Awards

    So much look for such a little lady.

  16. David Bowie at the 1975 Grammys

    43rd Annual Grammy Awards

    The Thin White Duke was in full effect

  17. Beyoncé at the 2014 Grammys

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    Bey didn’t walk the red carpet at the Grammys last year—she was too busy being poured into this getup for her “Drunk in Love” performance with Jay Z.

  18. Rihanna at the 2015 Grammys

    Singer arrives at the 57th GRAMMY Awards at Staples Center on February 8, 2015 in Los Angeles, California.

    Rih was serving us Loofah eleganza with a hint of Pepto Bismol.

  19. Dolly Parton at the 1977 Grammys

    The 19th Annual GRAMMY Awards

    Dolly kept her legendary cleavage under wraps, but just barely.

  20. Grace Jones at the 1980 Grammys

    The 25th Annual GRAMMY Awards - After Party at the Biltmore Hotel

    Only Grace could wear Rick James as a giant brooch.

  21. Toni Braxton at the 2001 Grammys

    43rd Annual Grammy Awards

    Hi, Toni! Hi, Toni’s butt and sideboob!

  22. Mariah Carey at the 1993 Grammys

    The 35th Annual GRAMMY Awards

    A vision of love.

  23. Christina Aguilera at the 2001 Grammys

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    X-tina was in her Dirrty phase.

  24. Sia at the 2015 Grammys

    Singer arrives at the 57th GRAMMY Awards at Staples Center on February 8, 2015 in Los Angeles, California.

    Accompanied by minni-me Maddie Ziegler, the reclusive singer’s massive wig had everyone gagging.

  25. Prince at the 1988 Grammys

    30th Annual Grammy Awards

    His name is Prince, and he is funky.

  26. Madonna at the 1999 Grammys

    2/24/99 Los Angeles, CA. Madonna performs live at the 41st Annual Grammy Awards.

    Let’s face it: Every Grammys outfit Madge wears is iconic, but this one was a keeper for us.

  27. Jennifer Lopez at the 2000 Grammys

    2000 GRAMMY Awards

    And America learned what double-sided tape was.

Dan Avery, Evan Ross Katz and Jon Adams contributed to this story