(Red Carpet)

Forget The Oscars, Can We Reminisce About These Iconic Grammys Looks?

Take a trip down memory lane.

Originally Published: 
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Iconic Grammys outfits

The 66th Annual Grammy Awards, which will air on Sunday Feb. 4, will be a special night for everyone in music. Year after year, the recording industry’s finest talents gather to honor the most outstanding musical achievements. The fashion is, of course, as important as the coveted accolades. The red carpet calls for extra impactful looks and bold expressions of personality. Ahead of the big night, look back on the most iconic Grammys outfits of all time. With over six decades of designer ensembles to see — the first show was in 1959 — there is a lot to reminisce about.

When you think about Grammys fashion, certain looks — like Jennifer Lopez’s Versace number from 2000 — might immediately come to mind. The outfit was so impactful that it even inspired a spinoff look on the Versace Spring/Summer 2020 runway. You may also recall Ariana Grande’s frothy princess gown by Giambattista Valli from the 2020 ceremony as a memorable fashion moment, or when Cardi B shut down the red carpet in her vintage Mugler Couture dress that resembled an oyster shell back in 2019.

Are you ready to take a trip down memory lane? If yes, keep scrolling to see the very best Grammys looks from years past, ahead.


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Cher had many memorable style moments at the Grammys, but fans will never forget her 1974 butterfly look.

Yoko Ono & John Lennon

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The duo’s 1975 Grammys looks feel as relevant today as they did decades ago. Ono teamed her sage green slip dress with a feathered shawl and a mini bag, while Lennon wore a hat to dress down his tuxedo-like outfit.


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TLC delivered an iconic fashion moment in girl band history when they wore a trio of gauzy, matching white ensembles for their first-ever Grammy appearance. Their outfits felt sporty and elegant.


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For some ‘90s outfit inspiration, check out Madonna’s white tank top and embellished purple pants look from the 1999 Grammys. On that night, she won four awards that included Best Pop Album for Ray Of Light.

Jennifer Lopez

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This Versace dress on J.Lo from the 2000 Grammys ceremony is one of the most iconic red carpet looks of all time. She even recreated the dress moment during the label’s Spring/Summer 2020 runway show.

Whitney Houston

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Houston held up her Grammy award win in 2000 while wearing a daringly sheer pink ensemble.

Destiny’s Child

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In 2001, Destiny’s Child not only swept the Grammys with their wins — they took home Best R&B Performance by a Duo or Group with Vocals and Record of the Year but the members also stunned in coordinating green ensembles by Tina Knowles, aka Beyoncé’s mom.

Toni Braxton

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Here’s hoping a celebrity will recreate this 2001 look from Toni Braxton because it is everything. The design, from the plunging neckline to the sultry cutouts, are all brilliant.

Sheryl Crow

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Crow brought some sunshine to the red (er, green) carpet in 2005, rocking a vibrant yellow gown with a dramatic midriff cutout from Roberto Cavalli.

Jennifer Hudson

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For the award show in 2007, Hudson looked breathtaking in a fiery red dress, which was adorned with a tiny gold snake embellishment, from Roberto Cavalli.

Lady Gaga

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Lady Gaga’s solar system-themed ensemble at the 2010 Grammys was one of the most avant-garde looks of the night. The outfit was by Giorgio Armani Privé.

Nicki Minaj

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Nicki Minaj pulled up to the 2012 Grammys in a red satin robe from Versace, as revealed by the house’s signature Medusa head on the skirt. For extra effect, she brought along a Pope impersonator as her date.


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In 2013, Adele strayed from her go-to all-black attire and opted for a pop of color with this floral dress by Valentino.

Katy Perry

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The music notes on Perry’s Valentino Haute Couture gown made a sweet reference to her craft at the 2014 Grammys.


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Zendaya opted for a menswear-inspired look by DSQUARED2 at the 2016 Grammys.

Selena Gomez & Taylor Swift

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That same year, Gomez and Swift arrived at the Grammys red carpet hand-in-hand. Gomez wore a shimmery navy blue gown by Calvin Klein while Swift opted for a two-toned red and fuchsia set from Versace.


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Rihanna’s rebellious two-piece gown by Armani Privé lit up the red carpet at the 2017 Grammys. She carried a black clutch from Roger Vivier and accessorized with sparkly jewels by Chopard.


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SZA looked ethereal at the 2018 Grammys in her dreamy silver gown by Atelier Versace.

Cardi B

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Cardi B stunned the crowd at the 2019 Grammys with her vintage oyster dress from Mugler Couture’s Fall/Winter 1995 collection. She wore a medley of pearl accessories and a pair of dramatic, blush pink opera gloves.

Tracee Ellis Ross

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Ross shut down the red carpet at the 2019 Grammys with her vibrant green pantsuit by Ralph & Russo. The actor’s fashion moment was complete with a reptile design around her waist, Lorraine Schwartz jewels, and a pair of heels from Christian Louboutin.

Ariana Grande

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Grande’s frothy gown by Giambattista Valli stood out at the 2020 Grammys. She completed her Cinderella look with matching opera gloves and a pair of diamond earrings by KALLATI.

Taylor Swift

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In 2021, Swift tapped into her romantic and sweet side in a mini dress from Oscar de la Renta. The long-sleeve number was crafted with pressed, real flowers.

Dua Lipa

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Lipa also stunned at the 2021 Grammys, wearing a butterfly motif dress from Atelier Versace. Past celebs who have also referenced the insect in their outfits at the Grammys include Cher in 1974 and Christina Aguilera in 2000, where she also wore a Versace number when she took home the Best New Artist award.

Harry Styles

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Always one to make a fashion statement, Styles stunned his fans in 2021 when he attended the Grammys in this Gucci look. Take note and add a purple feather boa to your next going-out ensemble.

Olivia Rodrigo


It was a big night at the 2022 Grammys for Rodrigo, who won three of her seven nominations for her debut album, Sour. She took home Best New Artist, Best Pop Vocal Album, and Best Pop Solo performance for “Drivers License.” To top this off, it was also the 20--year-old singer’s first-ever Grammy awards and she chose to wear this unforgettable optical-illusion dress from Vivienne Westwood.

Sam Smith

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It was impossible to miss Sam Smith’s dramatic red carpet moment at the 2023 Grammys. Matching with fellow musician Kim Petras, the “Unholy” singer brought the heat in a custom red Valentino look.

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