Listening to Taylor Swift’s release of Fearless (Taylor’s Version) has us feeling nostalgic as hell!

Not only are the rerecordings of her songs from the album even better than the originals, but she also gifted us with *six* amazing songs from the vault!

Her other vault songs include “Mr. Perfectly Fine”, “You All Over Me”, We Were Happy”, “That’s When”, “Don’t You”, and “Bye Bye Baby”. And, as Sophie Turner says, “Mr. Perfectly Fine” is not NOT a bop!

Fearless was Taylor’s big turning point in her career. Despite it only being her second album, Fearless won Album of the Year at the 2009 ACM Awards, 2009 CMA Awards, and the 2010 Grammy Awards.

Fearless was the first time the world saw her as a force to be reckoned with. And it’s no wonder — the album has classics like “Love Story”, “White Horse”, “Fifteen”, “Hey Stephen”, “You Belong to Me”, “Change” and so many others.

From the moment she dropped “Love Story” in September 2008, we knew Taylor was much, much more than just another country singer. She was a superstar inside and out.

Taylor’s Fearless era was pretty short-lived, however. Because this was back in the day when her record label had her dropping albums every two years like clockwork.

Fearless officially hit shelves in November 2008, she quickly went on tour in April 2009 until July 2010, and just one month later, she dropped her first single from Speak Now, “Mine.”

Fearless was mainly the era of knee-high boots, sequins and fringe, and her quintessential perfect country curls. But towards the end, we could already see Taylor’s styling evolving. She was starting to experiment with romantic florals, a touch of prep, and even straight hair (gasp!).

Below, relive some of Taylor’s most iconic outfits from her Fearless era, when our girl was young and carefree.

Oh, and did we mention we went ahead and recreated them with a modern update? Cuz, yeah, we totally did.

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1. CMA Awards, November 2008

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Taylor had a great night at the 2008 CMAs! Not only did she perform “Love Story,” but she also was nominated for Female Vocalist of the Year.

2. Clive Davis’ Pre-Grammy Party, February 2009

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Taylor rocked this super cute embellished mini dress by designer Collette Dinnigan to the party.

3. Grammy Awards, February 2009

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Taylor looked absolutely gorgeous in this black Kaufman Franco dress! Although she didn’t win any awards, she still showed up looking like the queen she is.

4. Brit Awards, February 2009

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Taylor showed up looking super cute in yet another Kaufman Franco dress. This time she opted for a mini sequin dress.

5. ACM Awards, April 2009

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Taylor absolutely slayed at the ACM red carpet in this Angel Sanchez red gown. She also scored big winning with Album of the Year for Fearless.

6. ACM Artist of the Decade, April 2009

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Taylor honored George Straight at the Artist of the Decade concert, rocking a cute white boho-chic frock with cowboy boots her signature glitter headband.

7. Out in London, May 2009

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Taylor was spotted in London wearing this romantic floral skirt by French Connection.

8. CMT Awards, June 2009

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Taylor walked the red carpet in this incredible Collette Dinigan dress! At the show itself, she took home the awards for Video of the Year and Female Video of the Year for “Love Story.” She also got to perform “Pour Some Sugar on Me” with Def Leppard!

9. BamaJam, June 2009

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Taylor took the stage at BamaJam where she performed both “You Belong With Me” and “Should’ve Said No” in a fun sequin fringe dress.

10. In London, August 2009

taylor swift fearless outfits

Taylor was spotted in London rocking a preppy look with this Ralph Lauren Crested Oxford Shirt and a blue pleated skirt.

11. Out in London, August 2009

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Still in London, Taylor opted for a more romantic look with this Lipsy sundress.

12. MTV VMAs, September 2009

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Ah, the infamous 2009 MTV VMAs. This was the award show when Kanye rudely interrupted Taylor’s acceptance speech for Best Female Video for “You Belong With Me.” She won of Beyonce’s “Single Ladies” video, which prompted Kanye to jump on stage with his “imma let you finish but…”

Despite the incident, Taylor kept cool, calm, and collected in her embellished one-shoulder Kaufman Franco dress.

13. In New York, September 2009

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Hanging out in New York, Taylor donned this super glam Rebecca Taylor Party dress and sky-high gold pumps.

14. CMA Awards, November 2009

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Taylor completely *owned* the 2009 CMAs! Not only did she slay in this ethereal Reem Acra dress, but she took home the awards for Entertainer of the Year, Female Vocalist of the Year, International Artist Achievement Award, Album of the Year, and Music Video of the Year.

15. Jingle Ball, December 2009

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Taylor looked festive as hell when she performed at the 2009 Jingle Ball in this sequin Jenny Packham mini dress.

16. Clive Davis’ Pre-Grammy Party, January 2010

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Taylor went with a silver sequin mini dress with fringe when she walked the red carpet at Clive Davis’ Pre-Grammy Party in 2010.

17. Grammy Awards, January 2010

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Back at the Grammy Awards, Taylor took the red carpet in this gorgeous Kaufman Franco off-the-shoulder gown.

At the show, she completely dominated, winning Album of the Year, Best Country Album, Best Female Country Vocal Performance, and Best Country Song. She also performed “You Belong With Me” with Stevie Nicks.

18. Brooks & Dunn the Last Rodeo Show, April 2010

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Taylor hit up Vegas in this incredible Jenny Packham purple fringe dress where she performed “Ain’t Nothin ‘Bout You” in honor of Brooks & Dunn.

19. Met Gala, May 2010

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At her second Met Gala, Taylor showed up in a dreamy Ralph Lauren cold-shoulder gown.

20. In New York, May 2010

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Back in New York, Taylor wore a charming Rebecca Taylor dress with a floral print.

21. CMT Music Awards, June 2010

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At the 2010 CMT Music Awards, Taylor opted for a slightly edgier look in this John Galliano floral jacquard mini dress. It was also one of the first times she went public with straight hair!

22. Songwriter’s Hall of Fame, June 2010

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Taylor attended the Songwriter’s Hall of Fame Ceremony in this romantic J. Mendel dress in lilac.

23. Fearless Tour, April 2009- July 2010

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Perhaps her most iconic look from her Fearless tour, this dress had it all: sequins, beads, and fringe! What more could a girl ask for?


Where to Buy All of Taylor Swift’s Outfits From Her Folklore & Evermore Era

Categories: Style & Beauty