Taylor Swift's Grammys Looks: Every Era, From Fearless 'Fits to Bejeweled Gowns

It's almost difficult to believe that Taylor Swift, multi hyphenate superstar and cultural icon, was once a teen girl skipping her senior prom to attend the 2008 Grammy Awards. But in many ways, Swift's relatability as a young dreamer is what has made her such a beloved force in popular culture. Since her Grammys red carpet debut, Swift's legions of fans, many who were aspiring singer-songwriters themselves, have enjoyed watching her attend music's biggest night, from her Best New Artist nomination (the trophy went to Amy Winehouse) to her many Album of the Year wins. (Swift is the first and only woman solo artist to win the Grammy for Album Of The Year three times for her solo recordings.)

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Swift could make history once again at the 2024 Grammys. If her album Midnights wins Album of the Year, she'll break the record for most Album of the Year wins. (She's currently in good company; she's tied with Frank Sinatra, Paul Simon and Stevie Wonder with three Album of the Year honors.)

Swift will walk the red carpet on Sunday, Feb. 4 at the Crypto.com arena in Los Angeles and fans are already speculating on what the "Anti-Hero" singer-songwriter will wear on the big night. Our money is on something Reputation-coded, not unlike what she wore to the 2024 Golden Globes.

Ahead of the ceremony, we're looking back at all of Swift's stunning Grammys looks, from red carpet showstoppers to bejeweled performance 'fits.

A Decade of Bejeweled Looks

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Swift made her Grammys red carpet debut at the 2008 ceremony. Her romantic violet gown was fitting for the "Love Story" singer's fairytale night.

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Swift looked sophisticated in a dramatic black gown for the 2009 ceremony. The same night, she made her debut Grammys performance when she performed her song "Fifteen" with Miley Cyrus.

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Years before she wrote "Bejeweled," Swift stunned in this shimmering midnight blue gown at the 2010 Grammy Awards, when she picked up her first Album of the Year trophy for "Fearless."

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Swift rocked a regal gown in 2012, the same year she picked up two trophies for her "ignore the haters" anthem "Mean."

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Swift looked like a goddess in this J. Mendel gown at the 2013 ceremony.

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Swift turned heads in a Gucci gown for the 2014 Grammys, during which she performed fan favorite "All Too Well."

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Swift entered her "1989" era in this head-turning aquamarine Elie Saab dress.

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Swift shut down the red carpet in this two-piece Versace look the same night she made headlines for her iconic speech in which she warned young women about "people along the way who will try to undercut your success or take credit for your accomplishments or your fame..."

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After a few years away, Swift made a grand return to the Grammys red carpet in this jaw-dropping floral Oscar De La Renta mini dress.

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Swift was fully in her "Midnights" era as she walked the red carpet in this beautiful Roberto Cavalli two-piece, accessorized with $3 million worth of Lorraine Schwartz jewelry and eye-catching earrings. Can you say bejeweled?

Beyond her legendary red carpet looks, Swift has always wowed with her on-stage performance looks. Ever since making her debut on the Grammys stage alongside Miley Cyrus for a performance of "Fifteen", Swift has excelled in showcasing looks that reflect where she is in her life and career. Take a look back at Swift's best Grammys performance looks below.

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Then teen queens Swift and Miley Cyrus took the stage to perform Swift's song "Fifteen."