Taylor Swift’s All-Time Greatest Fashion Moments


Taylor Swift‘s most memorable street style looks and award-show appearances throughout the years are right here. Let us check them out: 

With songs like “Tim McGraw” and “Teardrops On My Guitar,” Taylor Swift gained popularity as a teenage country singer and has since developed into one of the industry’s biggest names. Fans have witnessed the star through several eras, and there will undoubtedly be many more, from her smooth transition to the pop charts to her current residence in New York City.

It is inevitable that Swift’s style has changed with time. For her early red carpet appearances, the singer tended to wear beautiful ball gowns and feminine designs, but more lately, she has broken out of the mold with ensembles inspired by menswear and fitted suits. Swift will undoubtedly continue to astound us with her sense of style, whether she’s walking around Tribeca or attending an awards ceremony. This is also true of her songs.

Taylor Swift at the 2006 CMA Awards

Swift made her CMA debut shortly after dropping her very first single, “Tim McGraw,” which she wore to the floor in a black Elvira gown and black opera gloves. Her characteristic curls and dramatic, smokey makeup look were front and center. 


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Taylor Swift at the 2009 MTV VMAs

At the 2009 VMAs, Swift went all-out glamorous in a one-shoulder Kaufman Franco gown. Her long crystal earrings, wispy updo, and floor-length sequin dress were all unquestionably stunning choices. You might remember the Kanye West stunt from that!


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In 2010, Taylor Swift attended the 52nd Annual Grammy Awards.

At the 2010 Grammy Awards, the singer channeled her inner mermaid and wore a glittering green Kaufman Franco off-the-shoulder dress. She accessorized with thick silver bangles and a side-swept updo. Later that night, she posed with her medals while letting her golden curls fall down.

The 54th Annual GRAMMY Awards Red Carpet

LOS ANGELES, CA – FEBRUARY 12: Singer Taylor Swift arrives at the 54th Annual GRAMMY Awards held at Staples Center on February 12, 2012 in Los Angeles, California. (Photo by Larry Busacca/Getty Images For The Recording Academy)

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2012’s 54th Annual Grammy Awards with Taylor Swift

Swift, a veritable golden goddess, shone in a cap-sleeved Zuhair Murad gown as she walked the 2012 Grammy red carpet. The singer looked elegant and mature with her trademark curls brushed back into a tidy updo.

In 2013, Taylor Swift attended the 55th Annual Grammy Awards.

Swift deviated from the Grecian style as she walked the 2013 Grammy Awards red carpet, donning a cream J. Mendel gown with metallic accents and a plunging neckline. She wore her hair up in a braided manner and accessorized with delicate, modest jewelry.


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Taylor Swift at the 2013 MTV VMAs

2013 saw Swift embrace an obvious taste for old Hollywood elegance, which extended to the red carpet at the VMAs. The actress gave the look her all by accessorizing her Hervé Léger by Max Azria dress with sexy eye makeup, red lipstick, and finger-waved hair.


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2015’s 57th Annual Grammy Awards with Taylor Swift

Swift’s handmade Elie Saab halter dress stole the show on the 2015 Grammy red carpet. The singer accessorized her stunning turquoise dress with matching earrings and vivid fuchsia shoes for an even bolder pop of color.


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Taylor Swift at the 2015 VMA Awards

At the 2015 VMAs, Swift famously strolled the red carpet with her chic entourage. For the event, the singer wore a matching set of sequins by Houndstooth. She won video of the year for her hit song “Bad Blood.” She added matching metallic pumps as an accessory to the long-sleeve crop top and high-waisted harem pants.



Taylor Swift at the 2016 Met Gala

Swift donned a metallic silver Louis Vuitton minidress with a tiered ruffle skirt and cutout waist, in keeping with the Gala’s 2016 theme of Manus x Machina: Fashion in an Age of Technology. Her new platinum blonde hairstyle, which sharply contrasted with her black lipstick, was possibly the most stunning feature.

Eva Fehren rings, an edgy ear cuff, and black knee-high boots completed the ensemble.



Taylor Swift during the 2019 Time 100 Gala

Swift, who was about to enter her vibrant Lover phase, looked stunning on the red carpet at the 2019 Time 100 Gala in a pastel peach and yellow gown by J. Mendel. Her romantic updo, delicate headband, and Lorraine Schwartz gems further enhanced the ensemble.

2019 Billboard Music Awards with Taylor Swift

At the 2019 Billboard Music Awards, Swift, who is obviously becoming more daring with her looks, wore a purple Raisa & Vanessa minidress with ruffles. She accessorized the textured garment with diamonds from Stephen Webster, Moritz Glik, Jenny Dee Jewelry, and Stefere and Graziela Gems, as well as simple Casadei heels.

2021’s 63rd Annual Grammy Awards, featuring Taylor Swift

Swift appeared to be paying homage to her album Folklore, which earned the singer her third Album of the Year award that night, with her flower-embroidered Oscar de la Renta gown at the 2021 Grammy Awards.

The fashion house shared a behind-the-scenes glimpse of the garment’s creation on Twitter, showing the individual sewing of the plant appliqués. Swift walked the red carpet wearing the $8,990 dress in addition to Cathy Waterman jewelry and Louboutin heels. When needed, she put on a chic, matching flowery face mask.


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2022: Taylor Swift at the MTV VMAs

In August 2022, Swift triumphantly returned to the VMAs donning a stunning Oscar de la Renta minidress. She accessorized the glittering ensemble with Lorraine Schwartz pieces and Christian Louboutin heels that matched.

Swift made news at the event not just for her crystal-covered attire but also for revealing her new album, which would be released in October, as she accepted the video of the year award.



2023’s 65th Annual Grammy Awards with Taylor Swift

Swift wore a matching Roberto Cavalli floor-length skirt and a dark blue, long-sleeve crop top to the 2023 Grammy Awards.

The singer accessorized the sparkling two-piece with $3 million worth of Lorraine Schwartz jewelry, which included many rings and sapphire earrings, as if the crystal-adorned ensemble weren’t enough.



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