From Gaga to J.Lo, Here Are 18 Grammys Looks We’ll Never Forget

In honor of the 66th annual ceremony

grammy awards memorable looks
Scott Gries/ImageDirect

With its inventive musical performances and anything-goes red carpet, we like to think of the Grammy Awards as the Oscars’ rebellious musical cousin. And what better place for celebs to try out the ensembles of their eccentric dreams than a venue so, well, creative?

In honor of the 66th annual Grammy Awards—which will take place on Sunday, February 4—we’re taking a walk down memory lane. From Lady Gaga channeling Saturn to J.Lo’s legendary plunging Versace dress, here are 18 of the most memorable looks from Grammys past.

How to Live Stream the Grammys on February 4 (with or Without Cable)

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1. When Cher Was a Beautiful Butterfly (1974)

Long before she performed in nipple pasties, the “Believe” singer walked the red carpet in an outfit we swear we saw at Coachella.

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Kevin Mazur/Getty Images

2. And Lil’ Kim Left Her Pants at Home (1998)

One might say the “Lady Marmalade” rapper trail-blazed the way for Lady Gaga’s many pants-less looks.

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3. When J.lo Pledged Allegiance to Double-Sided Tape (2000)

This gauzy green Versace dress will never not be shocking.

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4. And Missy Elliott Worked It In a Sweat Suit (2003)

Elliott got her freak on and gave us all the Paris Hilton vibes in the process.

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5. When Lady Gaga Looked to the Stars for Fashion Inspo (2010)

What has more rings: Saturn or Gaga’s dress?

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6. And Nicki Minaj Took a Page Out of Little Red Riding Hood’s Playbook (2012)

Over the river and through the woods, to the Grammys she goes.

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7. When Pharrell Williams Donned the Sorting Hat from Harry Potter (2014)

Williams is definitely a Gryffindor.

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8. And Rihanna Wore a Loofah (2015)

Ri-Ri’s bringing sudsy back.

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9. When the Carters Looked Like IRL Bonnie and Clyde (2018)

Jay-Z and Yoncé let Blue Ivy shine like a diamond amidst their matching Bonnie and Clyde meets The Matrix looks.

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10. And When Pink Found Her Flock (2018)

Pinks of a feather flock together.

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11 When Cardi B Brought an Oyster as Her Plus-one (2019)

The chicest mollusk we ever did see.


12. When Billie Eilish Left Us Green with Envy In Her Gucci Ensemble (2020)

Not only did she win with this red carpet look, but she also won album of the year.

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Steve Granitz/WireImage

13. And When Ariana Grande Resembled a Disney Princess (2020)

She accessorized the one-of-a-kind Giambattista Valli dress with gloves and custom Louboutins.

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Kevin Mazur/Getty Images

14. When Taylor Swift Wore Florals for Spring (2021)

How groundbreaking.

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Jeff Kravitz/FilmMagic

15. When Tiffany Haddish Channeled Her Inner Grammy (2022)

Leave it to Tiffany Haddish to resemble the award itself.

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16. When Doja Cat Rocked Latex (2023)

We can only imagine how long it took her to get the dress on/off. 

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17. When Laverne Cox Brought Back the Peplum (2023)

Who said peplums were out of style?

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Jeff Kravitz/FilmMagic

18. And Finally, When Lizzo Proved That Orange Is Her Color (2023)

That cape is everything.

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Cat mom, yogi, brunch enthusiast

Lex is an LA native who's deeply obsessed with picnics, Slim Aarons, rosé, Hollywood history and Joan Didion. She joined PureWow in early 2017.


Senior Editor

Greta Heggeness is a California-based editor at PureWow and has been writing about entertainment since 2015. She covers everything from awards shows to exclusive celebrity...