STYLE EVOLUTION

Taylor Swift’s Style Evolution, From Cowboy Boots to Now

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Taylor Swift has proven so prolific over the course of her 15-year career, an album cycle can comprise the entire astrological zodiac. And as she ushered in the Lover era in 2019, even Swift herself knew that before she could move on from Reputation, she knew what she’d have to publicly declare about the old Taylor. The precocious, curly-haired country star who broke through with Fearless has come a long way between then and her two surprise 2020 releases, Folklore and Evermore, in addition to her recently re-released album, Fearless: Taylor’s Version, and the forthcoming Red: Taylor’s Version (which will boast 30 tracks). Her style, too, has been chronicled on many a red carpet, from the Country Music Awards to the Grammy Awards to the world premiere of her film Cats. See her current era’s red carpet debut, plus the rest of her best, most career-defining looks, here.

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Taylor Swift during 2006 CMT Music Awards red carpet at Curb Events Center at Belmont University in Nashville, Tennessee, United States.

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Taylor Swift arrives at the 41st Annual Academy of Country Music Awards in cowboy boots on May 23, 2006.

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Taylor Swift arrives at the 2007 CMT Music Awards.

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Taylor Swift performs onstage at the ACM New Artists Party For a Cause wearing some monogrammed cowboy boots on May 14, 2007.

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Taylor Swift arrives at the 41st Annual CMA Awards at the Sommet Center on November 7, 2007 in Nashville, Tennessee.

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Singer Taylor Swift arrives on the red carpet during the 50th Annual GRAMMY Awards on February 10, 2008 at the Staples Center, in Los Angeles.

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Taylor Swift went for a princess look with a pale pink gown at the 42nd Academy of Country Music Awards on May 15, 2007.

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Taylor Swift opted for a goth cowgirl moment when arriving at 2007 American Music Awards in Los Angeles on November 18, 2007.

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Taylor Swift shimmers in a gold gown at the "Superheroes: Fashion and Fantasy" themed Met Gala on May 5, 2008.

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Taylor Swift arrives on the red carpet of the 2008 MTV Video Music Awards on September 7, 2008 in Los Angeles, California.

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Taylor Swift attends the 42nd Annual CMA Awards at the Sommet Center on November 12, 2008 in Nashville, Tennessee.

Taylor Swift arrives to the 51st Annual GRAMMY Awards held at the Staples Center on February 8, 2009 in Los Angeles, California. Photo courtesy of Getty Images.

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Taylor Swift attends the Los Angeles premiere of Hannah Montana: The Movie (in which she also has a cameo appearance) on April 2, 2009.

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Taylor Swift arrives at the 2009 MTV Video Music Awards at Radio City Music Hall on September 13, 2009 in New York City.

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Taylor Swift attends “American Woman: Fashioning A National Identity” Costume Institute Gala on May 3, 2010 at The Metropolitan Museum of Art in New York City.

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Taylor Swift arrives at the 2010 American Music Awards held at Nokia Theatre L.A. Live on November 21, 2010 in Los Angeles, California.

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Taylor Swift arrives at the 2011 Billboard Music Awards at the MGM Grand Garden Arena May 22, 2011 in Las Vegas, Nevada.

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Taylor Swift arrives at The 54th Annual GRAMMY Awards at Staples Center on February 12, 2012 in Los Angeles, California.

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Taylor Swift arrives at 2012 MTV Video Awards at Staples Center on September 6, 2012 in Los Angeles, California.

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Taylor Swift arrives at the 55th Annual GRAMMY Awards at Staples Center on February 10, 2013 in Los Angeles, California.

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Taylor Swift arrives at the BBC Radio 1 Teen Awards at Wembley Arena in London on March 11, 2013.

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Taylor Swift arrives at the 2013 American Music Awards at Nokia Theatre L.A. Live on November 24, 2013 in Los Angeles, California.

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Taylor Swift attends the annual Victoria’s Secret fashion show at Earls Court on December 2, 2014 in London, England.

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Taylor Swift attends the 71st Annual Golden Globe Awards held at The Beverly Hilton Hotel on January 12, 2014 in Beverly Hills, California.

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Taylor Swift arrives at the 56th Grammy Awards held at the Staples Center in Los Angeles on January 26, 2014.

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Taylor Swift attends the “Charles James: Beyond Fashion” Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City.

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Taylor Swift wears a body suit the 2014 MTV Video Music Awards at The Forum on August 24, 2014 in Inglewood, California.

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Taylor Swift attends The 57th Annual Grammy Awards at the STAPLES Center on February 8, 2015 in Los Angeles, California.

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Taylor Swift attends the Elle Style Awards 2015 at Sky Garden @ The Walkie Talkie Tower on February 24, 2015 in London, England.

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Taylor Swift arrives at the 2015 iHeartRadio Music Awards at The Shrine Auditorium on March 29, 2015 in Los Angeles, California.

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Taylor Swift attends the 2015 Billboard Music Awards at MGM Grand Garden Arena on May 17, 2015 in Las Vegas, Nevada.

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Taylor Swift attends The 58th GRAMMY Awards at Staples Center on February 15, 2016 in Los Angeles, California.

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Taylor Swift attends the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at the Wallis Annenberg Center for the Performing Arts on February 28, 2016 in Beverly Hills, California.

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Taylor Swift attends “Manus x Machina: Fashion In An Age Of Technology” Costume Institute Gala at Metropolitan Museum of Art on May 2, 2016 in New York City.

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Taylor Swift attends the 64th Annual BMI Pop Awards held at the Beverly Wilshire Four Seasons Hotel on May 10, 2016 in Beverly Hills, California.

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Taylor Swift attends the 2018 American Music Awards at Microsoft Theater on October 9, 2018 in Los Angeles, California.

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Taylor Swift attends the 2019 iHeartRadio Music Awards on March 14, 2019 in Los Angeles, California.

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Taylor Swift attends the 2019 Time 100 Gala at Frederick P. Rose Hall, Jazz at Lincoln Center on April 23, 2019 in New York City. Photo courtesy of Getty Images.

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Taylor Swift attends the 2019 Billboard Music Awards at MGM Grand Garden Arena on May 1, 2019 in Las Vegas, Nevada.

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Taylor Swift attends FOX’s Teen Choice Awards 2019 on August 11, 2019 in Hermosa Beach, California.

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Taylor Swift meets fans at Tianhe Sports Center in Guangzhou, Guangdong Province of China on November 11, 2019.

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Taylor Swift attends the 2019 American Music Awards at Microsoft Theater on November 24, 2019 in Los Angeles, California.

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Taylor Swift attends Billboard Women In Music 2019 in Los Angeles, California on December 12, 2019.

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Taylor Swift arrives for Universal Pictures' world premiere of Cats in New York City on December 16, 2019.

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Taylor Swift attends the 77th Annual Golden Globe Awards at the Beverly Hilton Hotel on January 5, 2020 in Beverly Hills, California.

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Taylor Swift attends the Sundance Film Festival premiere of Miss Americana on January 23, 2020 in Park City, Utah.

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Taylor Swift attends the 63rd annual Grammy Awards on March 14, 2021 in Los Angeles, California.

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Taylor Swift poses on the red carpet at The BRIT Awards 2021 in London on May 11, 2021.