A Look Back at Taylor Swift’s 2008 ‘Fearless’ Album Fashion

Taylor Swift is on a mission to reclaim her work and she’s starting with her sophomore album, “Fearless.” In 2020, Swift announced that she had begun re-recording new versions of her old music after her entire Big Machine catalog was bought and then sold by Scooter Braun to a private equity company.

Today, she unveiled that “Fearless” would be the first release in the rollout of her re-recorded catalogs, and at midnight, “Love Story” will drop.

“My new version of Fearless (Taylor’s Version) is done and will be with you soon. It has 26 songs including 6 never before released songs from the vault,” Swift posted on Instagram Thursday morning. “Fearless (Taylor’s Version)” will be released on April 9 and feature 26 songs total, including hits such as “You Belong With Me” and “Fifteen.”

The original album released in 2008 to much fanfare, making it the most-awarded country album of all time. It won Album of the Year at the Grammys and it has sold over 12 million copies worldwide.

Swift was 19 years old when “Fearless” launched at just the start of her career. The singer was all cowboy boots and curly hair at the time. It may even be how we remember Swift best.

Her red carpet style in the aughts included lots of chiffon dresses and metallic heels. At her first Grammy Awards appearance, for instance, she wore a romantic, custom Sandy Spika gown in purple with embellished vine-like detailing.

©2008 NCNA PHOTO 310-828-3445February 10, 2008, Los Angeles, California2008 GRAMMY AWARDS ARRIVALS.XYZ (Mega Agency TagID: MEGAR108717_3.jpg) [Photo via Mega Agency]
Taylor Swift on the red carpet at the 2008 Grammys.
And at Clive Davis’ pre-Grammy party in 2008, she opted for a shimmering peach minidress paired with gold strappy stilettos.

Photos © 2008 The Grosby Group - Beverly Hills, February 09, 20082008 Clive Davis Pre-GRAMMY Party held at the Beverly Hilton Hotel.In this photo: Taylor SwiftPGrfj6 (Mega Agency TagID: MEGAR108716_3.jpg) [Photo via Mega Agency]
Taylor Swift at the 2008 Clive Davis Pre-GRAMMY Party held at the Beverly Hilton Hotel.
But when Swift hit the stage back then she stayed true to her country roots and was often seen in Western boots with an acoustic guitar in hand.

To see more of Taylor Swift’s style in 2008, click through the gallery.

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