Monica in 1999
Singer Monica wore a sleek column gown in 1999 that looked right at home on the red carpet.
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Mariah Carey’s LBD
In 1991, Mariah Carey rocked a little black dress, sheer panty hose and big hair that matched the prowess of her multi-octave pipes.
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Cher’s Lilac Mani
There is much to say about Cher's ensemble for the 1974 Grammys. The standout piece? Not the butterfly on her head, but the cool lilac manicure that would look completely right today, too.
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Connie Stevens’ Pixie Cut
At the 1967 Grammys, singer Connie Stevens sported an adorable pixie cut that today — nearly five decades later — is relevant in a major way.
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Gwen Stefani’s Sheer Gown
No Doubt frontwoman Gwen Stefani hit the 1998 Grammys with other half Gavin Rossdale and a killer sheer gown that kept her funky style intact while still looking sophisticated.
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Michael Jackson’s Metallic Tux Shirt
No male performer has done sparkle quite as well as Michael Jackson. And in the ’70s, he sported a metallic tuxedo shirt that served as a precursor for the amazing big-shoulder military jackets to come.
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Courtney Love’s Floral Crown
In 1998, Hole singer Courtney Love sported a floral crown that predated today's Brooklyn-favored trend of artsy hair flowers.
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Mick Jagger’s Turquoise and Gold Color Coordination
Rolling Stones legend Mick Jagger wore a perfectly coordinated turquoise and gold ensemble in 2011.
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Jill Goodacre’s ’90s White Dress
In 1991, model (and future Mrs. Harry Connick Jr.) Jill Goodacre looked every bit a '90s dream in a white gown on the Grammys carpet.
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Grace Jones’ Neon Makeup
In 1983, performer Grace Jones sported a head-turning ensemble topped with swipes of dazzling neon makeup we want to try ourselves, today.
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Fiona Apple’s Natural Face
Back in 1997, singer-songwriter Fiona Apple looked fresh-faced and beautiful with natural, dewy makeup that enhanced her features and let her natural beauty shine.
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Lionel Richie’s Gradient Glasses
At the 1983 Grammys, Lionel Richie, the iconic "Easy Like Sunday Morning" singer, rocked a pair of gradient shades deserving of weekday wear, too.
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Janet Jackson’s Boyfriend Blazer
Janet Jackson wore an androgynous blazer to the 1984 awards, and looked thoroughly modern in the process.
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Nelly Furtado’s Blood Orange Look
In 2002, Nelly Furtado scored Grammys gold in a blood orange gown complemented by matching lips.
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Whitney Houston’s Blue Dress
No Grammys style list is complete without Whitney Houston. And in 1986, the singer sported a blue gown that earned her a spot on our list.
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Olivia Newton-John’s Bob
In 1987, Grease star and singer Olivia Newton-John sported a darling bob.
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Katy Perry’s Pink Gown
Katy Perry ramped up the old-school glamour in 2009 when she wore a blush pink Basil Soda gown to that year's awards.
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Prince’s Polka Dots
In 1987, Prince proved that a man could rock polka dots as well as any woman.
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J. Lo in “The Dress”
In 2000, J. Lo changed the face of red carpet fashion forever by breaking out a barely-there Versace which, sources tell us, is currently on permanent display in the performer's house.
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Beyonce’s Colorblock Jumpsuit
In 2013, singer Beyonce looked modern and unique in a black-and-white colorblock jumpsuit by Osman.
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James Brown’s Brocade
We can get on up with this look.
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Alicia Keys’ Clear Louboutins
The singer started a trend in 2012 when she wore a pair of killer Christian Louboutin heels complete with PVC paneling.
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Lady Gaga’s Silver Sparkle
Image Credit: Photo Credit: Jon Kopaloff/Getty Images Gaga wowed in a glitzy silver custom Brandon Maxwell gown at the 2015 show.
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Kim Kardashian’s Deep V
Image Credit: Photo Credit: Jon Kopaloff/Getty Images Kim Kardashian stole the spotlight from Kanye West in a beaded Jean Paul Gaultier look.
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Rihanna’s Pink Poof
Image Credit: Photo Credit: Jon Kopaloff/Getty Images RiRi's love affair with tulle began with this Giambattista Valli puffy pink cloud in 2015.
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Taylor Swift’s Crop Top
Image Credit: Photo Credit: Steve Granitz/Getty Images The Versace two-piece that launched a thousand belly button conspiracy theories.
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Wiz Khalifa’s Casual Cool Tux
Image Credit: Photo Credit: John Shearer/Getty Images A cropped tailcoat and Converse made this the coolest look on the carpet in 2015.
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Jidenna’s Head-to-Toe Swag
Image Credit: Photo Credit: John Shearer/Getty Images From the pocket square to the smoking loafers, we could find no fault in Jidenna's 2015 look.
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Zendaya’s Mullet
Image Credit: Photo Credit: Jon Kopaloff/Getty Images Zendaya's 2016 tribute to David Bowie included a sharp double-breasted DSquared2 suit and a mullet.
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Sam Hunt’s Pink Crush
Image Credit: Photo Credit: John Shearer/Getty Images Country crooner Sam Hunt traded blue jeans for a pink Dolce & Gabbana suit.