STYLE EVOLUTION

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

Taylor Swift wearing florals
Photo by Kevin Mazur via Getty Images

Taylor Swift has proven so prolific over the course of her 15-year career, an album cycle can comprise the entire astrological zodiac. Even Swift herself knew that before she could move on to her Reputation era, she’d have to publicly declare the old Taylor “dead.” 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. And the Grammy Awards have chronicled that change, from her first nomination in 2008 to the six she’s up for this Sunday. See her current era’s red carpet debut, plus the rest of her best, most career-defining looks, here.

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

Taylor Swift arrives at the 2007 CMT Music Awards. Photo courtesy of Getty Images.

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

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. Photo courtesy of Getty Images.

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

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

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.

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. Photo courtesy of Getty Images.

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

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

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

Taylor Swift arrives at 2012 MTV Video Awards at Staples Center on September 6, 2012 in Los Angeles, California. Photo courtesy of Getty Images.

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

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

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

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

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. Photo courtesy of Getty Images.

Taylor Swift attends The 57th Annual GRAMMY Awards at the STAPLES Center on February 8, 2015 in Los Angeles, California. Photo courtesy of Getty Images.

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

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

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

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

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. Photo courtesy of Getty Images.

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. Photo courtesy of Getty Images.

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. Photo courtesy of Getty Images.

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

Taylor Swift attends the 2019 iHeartRadio Music Awards on March 14, 2019 in Los Angeles, California. Photo courtesy of Getty Images.

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.

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

Taylor Swift attends FOX’s Teen Choice Awards 2019 on August 11, 2019 in Hermosa Beach, California. Photo courtesy of Getty Images.

Photo via Getty Images

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

Photo by Frazer Harrison via Getty Images

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

Photo by Neilson Barnard via Getty Images

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

Photo by Kevin Mazur via Getty Images

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