Style-wise, the Grammys stand out from the rest of the award shows. Whereas Hollywood’s finest like to play it semi-safe at the Oscars and the Golden Globes, choosing pretty gowns and the occasional suit, those who attend music’s biggest night of the year rarely follow suit, with grandiose entrances and outfit changes a common occurrence. That’s how we ended up with such a wide array of daring looks from Grammys past, including J.Lo’s iconic Versace jungle gown, Cardi B’s Mugler oyster masterpiece and Rihanna’s bubblegum pink Giambattista Valli meme dress.
While, of course, we tune in to the Grammys each and every year for the performances and awards, like the hotly contested Album of the Year and Best New Artist, we also can’t help but have fashion be a main focus of the night. With the 66th Annual Grammy Awards behind us, we thought we’d take a trip down memory lane. Join in as we count off our all-time best-dressed looks from music's biggest night, including a couple of favorites from the 2024 Grammys.
This article was originally published in March 2020 and has since been updated.
Janelle Monáe, 2024
Janelle Monáe radiated glamour in this sequined Giorgio Armani Prive gown adorned with a plunging crystal-embellished neckline and sparkling silver and black rosette.Photo: Matt Winkelmeyer/Getty Images/The Recording Academy.
Miley Cyrus, 2024
With her feathered '70s hair and matching gold velvet Tabi heels, Miley Cyrus gleamed in custom Maison Margiela. Photo: Matt Winkelmeyer/Getty Images/The Recording Academy.
Queen Bey made history as the most awarded artist in history wearing a custom Gucci gown. Photo: Timothy Norris/FilmMagic.
Cardi B, 2023
Miss Belcalis Almanzar stunned in a dress by Gaurav Gupta Couture. Photo: Amy Sussman/Getty Images.
Doja Cat, 2022
Doja Cat didn't just wear one of the best Grammy dresses (made by Versace), but she unleashed the glass handbag trend when she wore this Coperni x Heven number. Photo: Frazer Harrison/Getty Images.
Megan Thee Stallion, 2021
Megan Thee Stallion didn't just win Best New Artist at the 2021 Grammys — she won Best Dressed, too. Photo: Kevin Mazur/Getty Images.
Ariana Grande, 2020
"Baby, you can shut up" if you don't like this 20-foot, custom Giambattista Valli gown on Ariana Grande. Photo: Steve Granitz/WireImage.
Billy Porter, 2020
Billy Porter's remote-controlled, rhinestone hat was enough to get him on this list. The rest of his teal-and-silver Baja East look was just icing on the cake. Photo: Axelle/Bauer-Griffin/FilmMagic.
Lizzo, 2020
Glamorous doesn't even begin to describe this Old Hollywood-inspired Versace gown on Lizzo. Photo: Steve Granitz/WireImage.
Lady Gaga, 2019
TBT to when Lady Gaga gave Celine's Hedi Slimane her red carpet stamp of approval. Photo: Dan MacMedan/Getty Images.
Chloe x Halle, 2019
Sisters who sing together, coordinate their red carpet fashion together. Photo: Lester Cohen/Getty Images.
Cardi B, 2019
Cardi B came out of her (vintage Mugler) shell for the 2019 Grammys. Photo: Dan MacMedan/Getty Images.
Taylor Swift, 2016
Normally a high-low, two-piece look wouldn't be our choice for a red carpet, but Taylor Swift's Versace look was equal parts glamorous and fresh.Photo: Axelle/Bauer-Griffin/FilmMagic.
Rihanna, 2015
In our book, Rihanna can do no wrong. But while everything the singer-designer does is a win for us, this bubblegum pink Giambattista Valli gown is a step above the rest. Photo: Jon Kopaloff/FilmMagic.
Destiny's Child, 2001
We didn't even notice the five Grammys on the floor because we were too busy admiring all three of these looks.Photo: Steve Granitz Archive 1/WireImage.
Britney Spears, 2000
This all-white look on Britney Spears doesn't get the recognition it deserves. Photo: Kevin Mazur/WireImage.
Jennifer Lopez, 2000
Name a more iconic outfit than J.Lo's Versace Jungle dress. We'll wait. Photo: Jeff Vespa/WireImage.
Mary J. Blige, 2000
The diamonds! The shawl! The hot pink color! Mary J. Blige did everything right at the 2000 Grammys.Photo: SGranitz/WireImage.
Jada Pinkett Smith, 1998
It's no wonder Jaden Smith is such a style star today. Just look at this naked dress his mom wore to the Grammys while she was pregnant with him. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
Lauryn Hill, 1997
Laid-back and sophisticated, this red-and-white dress was the winner at the 1997 Grammys red carpet. Photo: Kevin Mazur/WireImage.
Aretha Franklin, 1992
No one does leopard print quite like Aretha Franklin.Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
Prince, 1988
Only Prince could pull off literal head-to-toe polka dots. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
Grace Jones, 1983
No one out-styles Grace Jones. No one. Photo: Chris Walter/WireImage.
Yoko Ono & John Lennon, 1975
From the feathers to the Elvis nametag, Yoko Ono and John Lennon's Grammys looks were undeniably cool. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
Cher, 1974
Is it just me, or does Cher's butterfly-covered look from the 1974 Grammys belong on the fall '21 Blumarine runway? Photo: Michael Ochs Archives/Getty Images.
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