Style-wise, the Grammys stand out from the rest of the award shows. Whereas Hollywood’s finest like to play it 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.
With the 63rd Annual Grammy Awards airing on Sunday sans the extravagant red carpet we’ve grown accustomed to over the years, we thought we’d take a trip down memory lane. Ahead of Sunday night’s festivities, join in as we count off our all-time best-dressed looks from the days when red carpets didn’t take place primarily on Instagram.
Megan Thee Stallion, 2021
Megan Thee Stallion didn't just win Best New Artist at the 2021 Grammys — she won Best Dressed, too.
Ariana Grande, 2020
"Baby, you can shut up" if you don't like this 20-foot, custom Giambattista Valli gown on Ariana Grande.
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.
Lizzo, 2020
Glamorous doesn't even begin to describe this Old Hollywood-inspired Versace gown on Lizzo.
Lady Gaga, 2019
TBT to when Lady Gaga gave Celine's Hedi Slimane her red carpet stamp of approval.
Chloe x Halle, 2019
Sisters who sing together, coordinate their red carpet fashion together.
Cardi B, 2019
Cardi B came out of her (vintage Mugler) shell for the 2019 Grammys.
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.
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.
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.
Britney Spears, 2000
This all-white look on Britney Spears doesn't get the recognition it deserves.
Jennifer Lopez, 2000
Name a more iconic outfit than J.Lo's Versace Jungle dress. We'll wait.
Mary J. Blige, 2000
The diamonds! The shawl! The hot pink color! Mary J. Blige did everything right at the 2000 Grammys.
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.
Lauryn Hill, 1997
Laid-back and sophisticated, this red-and-white dress was the winner at the 1997 Grammys red carpet.
Aretha Franklin, 1992
No one does leopard print and fur quite like Aretha Franklin.
Prince, 1988
Only Prince could pull off literal head-to-toe polka dots.
Grace Jones, 1983
No one out-styles Grace Jones. No one.
Yoko Ono & John Lennon, 1975
From the feathers to the Elvis nametag, Yoko Ono and John Lennon's Grammys looks were undeniably cool.
Cher, 1974
Is it just me, or does Cher's butterfly-covered look from the 1974 Grammys belong on the fall '21 Blumarine runway?
