STYLE EVOLUTION

Taylor Swift’s Best Red Carpet Looks From Cowboy Boots to Oscar de la Renta Gowns

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Taylor Swift’s 15-year career has been comprised of many different looks and styles. With every new album came an updated aesthetic and red carpet looks to match. There was the curly-haired country girl of the Taylor Swift era and then the girly-girl of Fearless and Speak Now. Red brought a big more edge and, of course, a whole lot of red lipstick while Reputation brought out the singer’s edgy side. Lover introduced pastels and sparkles, and Folklore and Evermore fit perfectly into the cottagecore aesthetic that was popular during their releases. Throughout her long career, Swift has navigated eras, trends, and her own personal style like a pro and these days, she still surprises us every time she steps onto the red carpet. Of course, she has her favorites (Oscar de la Renta has been her go-to for a minute), but she’s not afraid to mix it up. So, as you make your way through Red (Taylor’s Version) and the ten-minute “All Too Well,” take some time to scroll through Swift’s best looks throughout the years.

2021: “All Too Well” Premiere
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Taylor Swift wears a velvet double-breasted Etro suit to the "All Too Well" premiere on November 12, 2021 in New York.

2021: Brit Awards
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Taylor Swift wore a silver Miu Miu two-piece at the Brit Awards 2021 on May 11, 2021 in London, England.

2021: Grammy Awards
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Taylor Swift wore a floral Oscar de la Renta mini dress to the 63rd Annual Grammy Awards in downtown Los Angeles, CA on Sunday, March 14, 2021.

2020: Miss Americana Premiere
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Wearing a houndstooth Carmen March jumpsuit and jacket, Taylor Swift attended the Netflix premiere of Miss Americana at Sundance Film Festival on January 23, 2020 in Park City, Utah.

2020: Golden Globes
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Taylor Swift wore a blue and yellow Etro dress to the 77th Annual Golden Globe Awards on January 5, 2020 in Beverly Hills, California.

2020: Cats Premiere
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Taylor Swift wore a strapless Oscar de la Renta gown to the world premiere of Cats in New York City on December 16, 2019.

2019: Billboard Women In Music
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Taylor Swift wore an Oscar de la Renta jumpsuit with chain details to the Billboard Women In Music 2019 in Los Angeles, California on December 12, 2019.

2019: American Music Awards
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Wearing a green asymmetric Julien Macdonald dress, Taylor Swift attended the 2019 American Music Awards on November 24, 2019 in Los Angeles, California.

2019: Teen Choice Awards
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Taylor Swift wore a multicolored Versace jumpsuit and jacket to the Teen Choice Awards 2019 on August 11, 2019 in Hermosa Beach, California.

2019: Billboard Music Awards
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Taylor Swift wore a lavender ruffled Raisa & Vanessa mini dress to the 2019 Billboard Music Awards on May 1, 2019 in Las Vegas, Nevada.

2019: Time 100 Gala
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Wearing a grecian J. Mendel dress, Taylor Swift attended the 2019 Time 100 Gala on April 23, 2019 in New York City.

2019: iHeartRadio Music Awards
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Taylor Swift wore a sequined Rosa Bloom romper to the 2019 iHeartRadio Music Awards on March 14, 2019 in Los Angeles, California.

2018: American Music Awards
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Taylor Swift wore a silver Balmain mini dress to the 2018 American Music Awards on October 9, 2018 in Los Angeles, California.

2016: BMI Pop Awards
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Taylor Swift wore a velvet Monique Lhuillier slip dress to the 64th Annual BMI Pop Awards on May 10, 2016 in Beverly Hills, California.

2016: Met Gala
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Taylor Swift wore a Louis Vuitton silver snakeskin dress to the “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.

2016: Vanity Fair Oscar Party
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Wearing an Alexandre Vauthier Spring 2013 couture dress, Taylor Swift attended the 2016 Vanity Fair Oscar Party on February 28, 2016 in Beverly Hills, California.

2016: Grammy Awards
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Taylor Swift wore a tube top and high-slitted skirt by Versace to the 58th Grammy Awards on February 15, 2016 in Los Angeles, California.

2015: Billboard Music Awards
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Taylor Swift wore a white cutout Balmain jumpsuit to the 2015 Billboard Music Awards on May 17, 2015 in Las Vegas, Nevada.

2015: iHeartRadio Music Awards
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Wearing a black cutout KaufmanFranco mini dress, Taylor Swift attended the 2015 iHeartRadio Music Awards on March 29, 2015 in Los Angeles, California.

2015: Grammy Awards
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Taylor Swift wore a turquoise Elie Saab gown to the 57th Annual Grammy Awards on February 8, 2015 in Los Angeles, California.

2014: MTV Video Music Awards
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Taylor Swift wore a Mary Katrantzou body suit to the 2014 MTV Video Music Awards on August 24, 2014 in Inglewood, California.

2014: Met Gala
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Wearing a pink embroidered Oscar de la Renta gown, Taylor Swift attended the “Charles James: Beyond Fashion” Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City.

2014: Grammy Awards
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Taylor Swift wore a shortsleeved silver Gucci dress to the 56th Grammy Awards in Los Angeles on January 26, 2014.

2014: Golden Globe Awards
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Taylor Swift wore a two-toned strapless Carolina Herrera gown to the 71st Annual Golden Globe Awards on January 12, 2014 in Beverly Hills, California.

2013: American Music Awards
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Taylor Swift wore a metallic Julien Macdonald mini dress to the 2013 American Music Awards on November 24, 2013 in Los Angeles, California.

2013: Grammy Awards
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Taylor Swift wore a grecian J. Mendel gown to the 55th Annual Grammy Awards on February 10, 2013 in Los Angeles, California.

2012: MTV Video Awards
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Taylor Swift wore a white J. Mendel suit to the 2012 MTV Video Awards on September 6, 2012 in Los Angeles, California.

2012: Grammy Awards
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Wearing a Zuhair Murad dress, Taylor Swift attended at the 54th Annual Grammy Awards on February 12, 2012 in Los Angeles, California.

2011: Billboard Music Awards
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Taylor Swift wore a strapless Elie Saab gown to the 2011 Billboard Music Awards on May 22, 2011 in Las Vegas, Nevada.

2010: American Music Awards
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Taylor Swift wore a Collette Dinnigan mini dress to the 2010 American Music Awards on November 21, 2010 in Los Angeles, California.

2010: Met Gala
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Taylor Swift wore a Ralph Lauren Spring 2005 RTW gown to the “American Woman: Fashioning A National Identity” Costume Institute Gala on May 3, 2010 at The Metropolitan Museum of Art in New York City.

2009: MTV Video Music Awards
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Taylor Swift wore a one-shoulder Kaufman Franco dress to the 2009 MTV Video Music Awards on September 13, 2009 in New York City.

2009: Hannah Montana: The Movie Premiere
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Taylor Swift wore a strapless Naeem Khan dress to the Los Angeles premiere of Hannah Montana: The Movie on April 2, 2009.

2009: Grammy Awards
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Taylor Swift wore a black, low-cut KaufmanFranco dress to the 51st Annual Grammy Awards on February 8, 2009 in Los Angeles, California.

2008: CMA Awards
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Taylor Swift wore a silver KaufmanFranco dress to the 42nd Annual CMA Awards on November 12, 2008 in Nashville, Tennessee.

2008: MTV Video Music Awards
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Taylor Swift wore a blush pink KaufmanFranco a-line dress to the 2008 MTV Video Music Awards on September 7, 2008 in Los Angeles, California.

2008: Grammy Awards
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Wearing a purple corseted Sandy Spika dress, Taylor Swift attended the 50th Annual Grammy Awards on February 10, 2008 in Los Angeles.

2008: Met Gala
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Taylor Swift wore a gold Badgley Mischka gown to the "Superheroes: Fashion and Fantasy" themed Met Gala on May 5, 2008.

2007: American Music Awards
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Taylor Swift wore a Catherine Malandrino jeweled halter dress to the 2007 American Music Awards in Los Angeles on November 18, 2007.

2007: Academy of Country Music Awards
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Taylor Swift wore a pink corseted Sandi Spika gown to the 42nd Academy of Country Music Awards on May 15, 2007.

2007: CMT Music Awards
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Wearing a BCBG Max Azria BCBG sequined dress, Taylor Swift attended the 2007 CMT Music Awards in Nashville, Tennessee on April 16, 2007.

2006: Academy of Country Music Awards
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Taylor Swift wore a handkerchief dress to the 41st Annual Academy of Country Music Awards in Las Vegas, May 23, 2006.

2006: CMT Music Awards
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Taylor Swift wore a white ruffled dress to the 2006 CMT Music Awards in Nashville, Tennessee on April 10, 2006.