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The Best Grammys Dresses & Red Carpet Looks Of All Time

By A Mystery Man Writer

Join in as we count off our all-time favorite standout looks from music
Join in as we count off our all-time favorite standout looks from music's biggest night, including a couple from the 2024 Grammys.

Beyoncé, 2023


Queen Bey made history as the most awarded artist in history wearing a custom Gucci gown.

Cardi B, 2023


Miss Belcalis Almanzar stunned in a dress by Gaurav Gupta Couture.

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 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.

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