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Wacky and Wonderful Grammys Looks Through the Years

Head-turning fashions at the annual music awards show

spinner image Michael Jackson holding several trophies in his arms at the 26th Annual Grammy Awards; Shania Twain on the red carpet at the 65th Grammy Awards
(Left to right) Michael Jackson at the 26th Annual Grammy Awards on Feb. 28, 1984; Shania Twain at the 65th Grammy Awards on Feb. 5, 2023.
Doug Pizac/AP Photo; Amy Sussman/Getty Images

There is red-carpet fashion — then there is Grammys red-carpet fashion.

Music’s biggest night has always been known for its over-the-top stunts (Lady Gaga arriving in a pod) and cutting-edge looks (J.Lo’s cut-down-to-there gown).

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In advance of the awards’ 66th anniversary show — which airs Sunday, Feb. 4, at 8 p.m. ET on CBS — here’s a look at some of the most talked-about style moments from years past. And make sure to check back here for all of our post-Grammy coverage.

spinner image Cher at the 16th Annual Grammy Awards
Michael Ochs Archives/Getty Images

Cher, 1974

The original over-the-top style icon, Cher never disappoints. At the 1974 Grammys, the singer wore a sheer flowing top, harem pants and a bikini-style bandeau adorned with a sequined butterfly. To crown the look, a matching butterfly clip held back her long jet-black locks.

spinner image Shania Twain on the red carpet at the 65th Grammy Awards
Amy Sussman/Getty Images

Shania Twain, 2023

Country music superstar Shania Twain channeled The Cat in the Hat in a black-and-white polka-dot suit with a spotted, oversize topper, designed by Harris Reed. The crowning glory? A long, fire-engine-red wig with bangs. “You just never know what to expect now!” the “That Don’t Impress Me Much” singer told People and EW about her unique look. “I’m gonna keep you guessing!”

spinner image Michael Jackson wearing sunglasses at the 26th Annual Grammy Awards
Ron Galella/Ron Galella Collection via Getty Images

Michael Jackson, 1984

The King of Pop drew attention — and, at the time, a record-breaking eight awards — at the 26th Grammys. Jackson wore a military-style sequined jacket with epaulets, aviator glasses and his signature white glove (sequined, of course).

spinner image Jennifer Lopez at the 42nd Annual Grammy Awards
Brenda Chase/Getty Images

Jennifer Lopez, 2000

When it comes to top award show style moments, Jennifer Lopez’s jaw-dropping Versace gown worn to the 42nd Grammys wins hands down. The sheer emerald chiffon number that plunged open to below her navel made headlines around the world — and changed red-carpet fashion expectations forever.

spinner image Bette Midler and Stevie Wonder hug at the 17th Annual Grammy Awards
(Left to right) Bette Midler and Stevie Wonder at the 17th Annual Grammy Awards.
Ron Galella/Ron Galella Collection via Getty Images

Bette Midler, 1975

Even in 1975, Bette Midler understood the assignment. At the 17th annual awards show, the Divine Miss M wore a classy black sequined gown with an actual 45 record —“ ‘Come Go With Me’ by the Del-Vikings,” she announced — as a hat.

spinner image Grace Jones at the 25th Annual Grammy Awards
Chris Walter/WireImage

Grace Jones, 1983

Grace Jones brought her avant-garde style to a new level at the show’s 25th anniversary. The “Slave to the Rhythm” singer donned a black Issey Miyake leather dress with an umbrella-shaped hat accented by bold futuristic makeup.

spinner image Alicia Keys in the press room at the 46th Annual Grammy Awards

Alicia Keys, 2004

Keys gave new meaning to “dress-casual” at the 2004 Grammys. For the 46th show, the “Fallin’ ” songstress wore a fancy flowing gown-style top paired with casual jeans and high heels.

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spinner image Mary J. Blige holding her Grammy at the 38th Annual Grammy Awards

Mary J. Blige, 1996

At the 38th annual Grammy Awards, Mary J. Blige sported a head-to-toe leopard print jumpsuit complete with hood, black glasses and leather gloves. The extra bling? Her award for best rap performance by a duo.

spinner image Cardi B on the red carpet at the 61st Annual Grammy Awards
Dan MacMedan/Getty Images

Cardi B, 2019

Remember when Icelandic artist Björk wore a swan dress to the 2001 Academy Awards?

Well, Cardi B one-upped her in this vintage Givenchy number. The rapper hit the Grammy red carpet dressed as a human pearl in Mugler Couture’s pink satin and black velvet Venus oyster-shell ensemble, topped with a pearl “hat.”

spinner image Lady Gaga at the 58th Annual Grammy Awards

Lady Gaga, 2016

Subtle she is not. In 2016, Lady Gaga wore a bold Marc Jacobs blue embroidered gown and red wig inspired by David Bowie’s “Life on Mars?” look. A mega-fan, Gaga’s six-minute musical tribute to the late star’s life included “Fame,” “Under Pressure” and “Let’s Dance.”

spinner image Madonna on the red carpet at the 57th Annual Grammy Awards
David Crane/MediaNews Group/Los Angeles Daily News via Getty Images

Madonna, 2015

The Material Girl channeled a well-dressed matador at the 57th Grammys with a custom black-and-white Givenchy bustier dress, fishnet stockings and chic veiled hat. The megastar pushed the envelope even further with over-the-knee black lace-up boots complete with nail heels.

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