Throwback Grammy Red Carpet Outfits

by Andrea Wurzburger 1/26/2018

The early 2000s were quite the time for red carpet fashion. Jeans with heels, crushed velvet suits, and crop tops galore. Wanna feel old? 18 years ago, Jennifer Lopez had jaws dropping everywhere when she stepped onto the Grammys red carpet in that green Versace dress. Click through this gallery to see some of our favorite throwback red carpet pics from the Grammys of yesteryear. WARNING: Major nostalgia ahead. Go ahead and prepare yourself by digging through your closet and pulling out your plastic chokers, hip hugger jeans, and fedoras. We can’t promise you won’t want to time travel back to 2003.

1 Alicia Keyes (2004)

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Was it a dress? Was it a shirt? We’re not sure, but there were no rules in 2004 fashion.
2 Christina Aguilera (2000)

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Do you think Christina called her stylist and just said, “I want sequins. How many? All of them. And a giant butterfly for good measure.”
3 Christina Aguilera (2001)

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And here she is again, giving her best impression of a pirate at the height of her dirrty phase.
4 Britney Spears (2000)

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Bless this sequined spaghetti strap crop top and the yards of fabric Brit Brit is using as a shawl. (Shawls were big in the early 2000s.)
5 Britney Spears (2002)

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The higher the hair, the closer to God.
6 NYSNC (2000)

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I have something to say about every single one of these tuxedos, but I’m not sure if I should start with Justin Timberlake’s golden shirt and velvet coat or JC Chasez’s all beige ensemble (turtle neck included.)
7 J. Lo and P. Diddy (2000)

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Who could forget the dress of the early 2000s? Iconic.
8 Traci Bingham (2001)

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Ah, yes, I almost forgot that body art was a thing. Thanks for reminding me, Traci Bingham.
9 Sisqo (2000)

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There’s a lot going on with Sisqo’s outfit here. But hey, whatever makes your booty go…
10 Penelope Cruz (2005)

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Penelope Cruz knows that every ensemble needs a fedora.
11 Sheryl Crow (2005)

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This dress was something straight of my high school’s 2005 prom. But no one at prom had Sheryl’s abs.
12 Aaron Carter (2000)

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That all-white tuxedo and that power stance, though.
13 Destiny’s Child (2002)

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Known for their matching ensembles, each of these ladies is wearing at least one early 2000s fashion staple.
14 Toni Braxton (2001)

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Hey, if you got those legs, you better flaunt those legs!
15 Lil’ Kim (2002)

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Lil’ Kim rolled up to the Grammys in an outfit that was more red than the carpet could ever hope to be.
16 Missy Elliot (2003)

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I miss the days were a velour tracksuit and fuzzy hat was considered awards show attire.
17 Imogen Heap (2007)

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Oh no, baby. What is you doin’?
18 Outkast (2002)

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Allow me to direct your attention to this dynamic duo and their choice of hats.
19 Gretchen Wilson (2005)

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The country singer is wearing what even early 2000s girl did to be fancy: Flared jeans, pointy-toed heels, and a halter.
20 Jane Krakowski (2000)

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Red leather must have been a very big trend.
21 Britney Spears and Justin Timberlake (2001)

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Not technically from the Grammys, but I couldn’t leave this one out! The year was 2001 and Britney and Justin were still an item…a denim-covered item.