25 Grammy Awards Fashion Moments Worth Revisiting

Perrie Samotin
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25 Grammy Awards Fashion Moments Worth Revisiting
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Up next on the awards season docket: The 59th Annual Grammy Awards, which airs live on Sunday. Naturally, we’re already anticipating what some of music’s biggest stars will be wearing (or not wearing, if history is any indication) on the red carpet.

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It’s a known fact that—more than every awards show there is—Grammys fashion is full of style risks, wild looks, and generally outrageous antics (ahem, Lady Gaga showing up in a giant egg in 2011).

Just in time for Sunday’s festivities, we decided to take a walk down memory lane and round up the 25 most unforgettable Grammys fashion moments of all time, including Cyndi Lauper’s insanely colorful ensemble from 1984, Jennifer Lopez’s infamous green Versace gown from 2000, and a couple of, um, dramatic looks from Nicki Minaj over the years.

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Click through the slideshow to see which celebrities scored a spot on our list.

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Click through the gallery for 20 unforgettable Grammy Awards dresses.

Jennifer Lopez wore this unforgettable green Versace gown to the 2000 Grammy Awards. Her wardrobe choice is still one of the most talked about in awards show history.

So unusual, indeed: Cyndi Lauper was her usual colorful self at the 26th Annual Grammy Awards in 1984.

Photo: Ron Galella/WireImage

Destiny's Child rocked their standard "same but different" ensembles in 2001.

Photo: Jason Kirk/Getty Images

Grace Jones at the 1984 Grammys.

Photo: Barry King/WireImage

That's Lady Gaga inside an egg-like container in 2011.

Photo: ROBYN BECK/AFP/Getty Images

Rihanna wore Jean Paul Gaultier to the Grammy Awards in 2011. The fashion-forward gown featured a sheer striped pattern on the off-the-shoulder cut. She joked, "I pretty much snatched it off the runway." And she pretty much did.

Photo: KENNELL KRISTA/SIPA/SIPA

Madonna and Shania Twain looking oh-so-late-'90s at the 41st Annual Grammy Awards in 1999.

Photo: KMazur/WireImage

Sweet braids: Christina Aguilera during the 43rd Annual Grammy Awards in 2001.

Photo: Jeffrey Mayer/WireImage

Nicki Minaj wore one of the most memorable Grammy Awards look ever in 2012 by opting to don a custom Versace cape dress. The Red Riding Hood–inspired gown definitely stood out on the red carpet.

Photo: Jason Merritt/Getty Images

At least she added some pointy pumps: Missy Elliott at the 2004 Grammy Awards.

Photo: SGranitz/WireImage

Yikes: Sheryl Crow in 2002.

Photo: Jeff Kravitz/FilmMagic

Haim earning their title as chicest band ever.

Fergie wore a daring sheer lace neon orange gown by Jean Paul Gaultier to the 54th Grammy Awards.

Photo: Jason Merritt/Getty Images

Lil' Kim shows off her assets in 2004.

Photo: Jeffrey Mayer

Sinead O'Connor in a tee in 1989.

How times have changed: Miley Cyrus in a tiger-print sequined Roberto Cavalli gown in 2011.

Photo: Jason Merritt/Getty Images

Cotton candy or dress? You decide.

In 2010, Jennifer Hudson stunned the world when she debuted her super-slim body on the Grammys red carpet.

Whitney Houston at the Grammys in 1986.

Photo: Ron Galella/WireImage

Oh, 2010 Britney.

We miss 2012.

Charli XCX getting formal in 2015.

Someone who actually wanted to look nice at the Grammys!

The hat was definitely necessary.

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