From Gaga to J.Lo, 15 Grammys Looks We’ll Never Forget

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 65th annual Grammy Awards—which will take place on Sunday, February 5—we’re taking a walk down memory lane. From Lady Gaga channeling Saturn to J.Lo’s legendary plunging Versace dress, here are 15 of the most memorable looks from Grammys past.

How to Live Stream the Grammys Online

cher 1974 grammys
Michael Ochs Archives/Getty Images

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.

lil kim grammys
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.

j lo grammys green dress
Scott Gries/Getty Images

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

This gauzy green Versace dress will never not be shocking.

missy elliot grammys
Jeff Kravitz/Getty Images

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.

lady gaga grammys1
Dan MacMedan/Getty Images

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

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

nicki minaj grammys
Jason Merritt/Getty Images

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.

pharrell williams grammys hat
Christopher Polk/Getty Images

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

Williams is definitely a Gryffindor.

rihanna grammys pink dress
Jon Kopaloff/Getty Images

8. And Rihanna Wore a Loofah (2015)

Ri-Ri’s bringing sudsy back.

the carters at the grammys
Christopher Polk/Getty Images

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.

pink in feathered dress
Dimitrios Kambouris/Getty Images

10. And When Pink Found Her Flock (2018)

Pinks of a feather flock together.

cardi b grammys oyster dress
Amy Sussman/Getty Images

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.

ariana grande grammys
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.

taylor swift grammys1
Kevin Mazur/Getty Images

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

How groundbreaking.

grammy awards tiffany haddish
Jeff Kravitz/FilmMagic

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

Leave it to Tiffany Haddish to resemble the award itself.

Stay up-to-date on every breaking celebrity story by subscribing here.

The 15 Most Shocking Grammys Moments of All Time

Lex Goodman

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.
read full bio

Greta Heggeness

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...
read full bio