Celeb Style
Taylor Swift's style evolution, just in time for 'Midnights' album release.
Taylor Swift’s Style Evolution Has So Many Eras, Just Like Her Music

She’s a Tennessee Stella McCartney.

by Haylee Thorson and Jordan Murray
Originally Published: 
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Over the past 17 years, Taylor Swift’s style evolution has directly correlated with her ever-evolving sound. From country sweetheart to pop sensation, rebellious rockstar to cottagecore queen, the 11-time Grammy winner has had more fashion — and music — eras than any other musician in her generation.

Throughout her career, Swift has been a chameleon of sorts. Each of her albums is defined by its own unique sound and aesthetic. The re-emergence of a new album and, subsequently, a new Swift, is reflected in every element of her exterior persona from her music videos to her red carpet fashion choices. Whether it be the heat-styled curls and cat eye makeup of her Speak Now era, the blunt bangs and pinstripes of her Red era, or the vampy lips and bold bodysuits of her Reputation era, she is a style shapeshifter.

In 2006, 16-year-old Swift made her country music debut with the hit single “Tim McGraw'' and her sequential self-titled album Taylor Swift. Known then for her signature blond curls, cowboy boots, and sweet disposition, the singer-songwriter soon became a household name. However, as time progressed, she began drifting away from her country roots and experimenting with an array of different genres, each with its own corresponding look. Since then, Swift has released nine more studio albums (ranging from country to pop to folk), broken countless records, and continues to go down in history as one of the most decorated and transformative musicians of all time.

As you’re in the midst of your Eras Tour concert movie rewatch and 1989 (Taylor’s Version) listening sessions, take a look at Taylor Swift’s style evolution from 2006 to now.

2006: Taylor Swift In a Sundress & Cowboy Boots

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This is the vibe that started it all. Swift’s early red carpet looks often consisted of flowy sundresses, beat-up cowboy boots, and of course, her then-signature honey-blonde curls. Arriving at the Academy of Country Music Awards a month before the release of her debut single, “Tim McGraw,” the 16-year-old country musician had no idea her life was about to change forever.

2006: Taylor Swift In A Black Mermaid Dress

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Taken only a few months after her first appearance at the Academy of Country Music Awards in 2006, Swift’s red carpet look at the ‘06 CMA Awards was a complete 180. Dressed in a floor-length black satin gown and matching gloves, the singer’s Old Hollywood ensemble was a departure from her typically sweet, feminine style. However, her signature cat eyeliner and bouncy curls remained.

2008: Taylor Swift’s “Love Story” Princess Era

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Nominated for Best New Artist, Swift first attended the Grammys in ‘08. For the event, Swift’s lilac gown foreshadowed her soon-to-come “Love Story” era. Featuring a gown with a silk corset bodice and cascading textured skirt, diamond drop earrings, and shoulder-length ringlets, this regency-reminiscent look was the epitome of opulence. In the months surrounding the release of her second studio album Fearless, Taylor’s style—on and off the red carpet—was almost always fit for a princess.

2009: Taylor Swift Wearing A Headband

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In 2009, the quintessential Swift outfit consisted of three things: a statement headband, a boho sundress, and a pair of cowboy boots. Comprised of a lacy white v-neck dress, shimmery silver headband, and cascading spiral locks, this look from the ACM Artist of the Decade event perfectly encapsulated the young musician’s shifting style.

2010: Taylor Swift In A Shimmery Mini Dress

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As Swift’s sound transitioned from classic country to country pop, so too did her style. During her performance of “You Belong With Me” at the 2010 NFL Opening Kickoff, the 20-year-old rocked a glittery silver fringe dress, black knee-high boots, and her signature red lip. Perhaps the most illustrative of her shift to a new persona was her choice of guitar. Silver and sparkly, Swift’s guitar was emblematic of her evolution from country girl to pop princess.

2012: Taylor Swift’s Preppy Side

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Swift’s Red era was accompanied by an entirely new aesthetic. Characterized by long straight hair, blunt bangs, and a bold red lip, her new aesthetic was directly tied to her fourth studio album release. In terms of fashion, Swift’s country sweetheart style became more mature, as reflected by her outfit at the 2012 MTV Video Music Awards. Featuring a red-and-white striped three-quarter tee, black high-waisted shorts, and red oxford flats, Swift’s ensemble was the blueprint for many looks to follow.

2014: Taylor Swift’s Short Shorts Bodysuit

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1989 was a cultural reset for Swift and the style she channeled at the time proved it. The 24-year-old’s taste transformed yet again, as did her music. Swift’s fifth studio album was the epitome of pop. Embodied by hits like “Blank Space” and “Welcome to New York,” her sound had more of an edgy, city girl feel, and her outfit at the 2014 MTV Video Music Awards reflected that. Donning a bold blue playsuit, burgundy Elie Saab heels, and a shoulder-length textured bob, Swift was entering her era of avant-garde looks.

2016: Taylor Swift Wins Big In A Two-Toned Two-Piece

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T-Swift’s two-toned Atelier Versace ensemble and ultra-straight bob at the 58th Grammy Awards were far different from the fairytale periwinkle gown and soft ringlets she wore to her first Grammy Awards in 2008. With seven Grammy nominations, Taylor was expected to serve on the red carpet and she did not disappoint. The coral bandeau and hot pink satin slit skirt were a bold choice for the “Shake It Off” singer, but this was still one of her most memorable looks (and award-winning moments) to date.

2016: Taylor Swift’s Edgy Alter Ego

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Everything changed for Swift at the 2016 Met Gala. From her hair to her makeup to her style, she looked like a completely different person at the “Manus X Machina: Fashion in an Age of Technology” themed event. Her metallic snakeskin Louis Vuitton mini dress and knee-high gladiator sandals foreshadowed the Reputation period that was to come.

2018: Taylor Swift, Casual In Denim Cutoffs

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In the months following Reputation’s release, Swift’s New York City street style looks were characterized by neutral-toned oversized blouses and tiny cutoff shorts. Her red lipstick, wheat-colored waves, and blunt bangs were reminiscent of her preppy Red era, but the ultra-distressed denim and embellished leather boots added an edge reflective of her spunky sixth studio album.

2019: Taylor Swift, Romantic In Ruffles

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Whimsical and dreamlike, Swift’s ruffled pastel mini dress and subtle, romantic makeup at the 2019 Billboard Music Awards embodied big-time Lover vibes. The 29-year-old wore this eccentric lilac outfit to the Billboard Awards in 2019, mere months before the release of her seventh studio album. Starkly departing from her edgy, rebellious Reputation era, Swift’s style and sound were about to become much more bubbly.

2019: Taylor Swift, Vibrant In Versace

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Just like the affirming LGBTQ+ message behind her hit single “You Need to Calm Down,” Swift’s outfit at the 2019 MTV Video Music Awards was bold and unapologetic. Wearing a vibrant, beaded Versace blazer dress, thigh-high black boots, and an iconic red lip, the star was up for 12 different VMA award category nominations. Winning “Video Of The Year” a decade after the infamous run-in with Kanye West in 2009 was an unforgettable moment in Swift’s time-honored career.

2021: Taylor Swift’s Floral Folklore Moment

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Folklore, Swift’s eighth studio album, was a major dose of the cottagecore aesthetic. Therefore, it was only fitting for the “Cardigan” singer to wear a garden-inspired outfit, covered in floral embellishments, to the Grammy Awards in 2021. As the album name suggests, folklore ushered in a new era of Taylor — one characterized by indie folk, delicate silhouettes, and soft hair and makeup.

2021: Taylor Swift’s All Too Well Power Suit

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Swift’s 2021 All Too Well: Short Film premiere was all about reclaiming power. Starring Stranger Things actor Sadie Sink and The Maze Runner’s Dylan O’Brien, Swift’s cozy, yet gut-wrenching short film truly felt like “autumn leaves falling down like pieces into place,” and her jewel-toned velvet pantsuit embodied that vibe. This outfit ushered in the current era of Taylor’s style — moody, yet sophisticated.

2022: Taylor Swift’s 2009 VMAs Tribute

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Swift’s style evolution came full circle at the 2022 MTV Video Music Awards. For her first public event in years, Swift wore a shimmering silver mini dress paired with a classic red lip. If the look feels reminiscent of one of her earlier VMAs moments, that’s because it is. Fans pointed out that Taylor’s ensemble was eerily similar to what she wore in 2009 when Kanye West interrupted her acceptance speech for Best Female Video in 2009, possibly hinting at a Reputation re-release.

June 2023: Taylor Swift’s Collegiate Vibes

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While her red carpet and concert looks are always ultra-sparkly, T-Swift toned it down for her days off, channeling a very collegiate vibe in spring 2023 with a red floral corset-style stop, black shorts, sling-back loafers, and a chic pair of tortoise sunnies while in the West Village area of NYC.

August 2023: Taylor Swift’s Eras Era

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Swift’s Eras Tour that has been everywhere since its start in March 2023, showing off dozens of custom lewks. While performing on the tour stop in Mexico City in August, she wore a lavender Nicole + Felicia gown to represent her “Speak Now” era.

September 2023: Taylor Swift, Sultry In Versace

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Switching it up from her usually very bright red carpet looks, Swift went for a more sultry vibe for the 2023 MTV Video Music Awards. She wore a side-slit black Versace gown with layered gold jewelry and simple black heels as she strutted down the carpet.

October 2023: Taylor Swift’s 1989 Throwback

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At the premiere of Swift’s Eras Tour concert film on Oct. 11, the woman of the hour was so 1989 (Taylor’s Version)-coded, fans were screaming, crying, throwing up. Weeks ahead of the re-release, the singer wore a blue Oscar de la Renta ball gown, complete with floral embroidery and cutout details, in the same shade as the album’s cover.

Her faux bob hairstyle also gave nods to the OG release, as Swift was known for her textured bob at the time. (Scroll back up to 2014 if you need proof.)

October 2023: Taylor’s Game Day Era

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In more recent weeks, Swift has been rockin’ a blokette aesthetic as she watches new boyfriend Travis Kelce at his Kansas City Chiefs games. On Oct. 22, his team played against the Los Angeles Chargers at Arrowhead Stadium, and the singer was pictured watching the game while sporting a Chiefs sweatshirt in support of the athlete.

November 2023: Taylor Swift’s Easter Egg-Filled Gown

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So many nods, so little time. At the London premiere of Beyoncé’s concert film, Swift stayed on theme to support her longtime friend, showing up in Queen Bey’s signature Renaissance color, silver.

Mind you, the metallic could also be another hint at the upcoming release of Reputation (Taylor’s Version), considering there’s a snake embellishment along the neckline, as well as be an homage to “Bejeweled” or “Mirrorball.” Knowing Swift’s penchant for Easter eggs and hidden details, it’s probably a combo of all of ‘em.

January 2024: Another Reputation (TV) Easter Egg??

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On the first big night of awards season, the singer — who’s nominated for cinematic and box office achievement, thanks to the Eras Tour movie — wore a green Gucci dress reminiscent of the snake motif strewn throughout her Reputation album. Could this be another Reputation (Taylor’s Version) Easter egg?

January 2024: Taylor Swift’s “Debutation” Era

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Wearing snakeskin thigh high boots, Tay seemingly hinted at Reputation (TV) again during a girls’ night out with Blake Lively in January 2024. But, considering the sweet, country-like look of her velvet mini dress, fans believe she was also paying tribute to her eponymous debut album; they’re even referring to the aesthetic as “Debutation.”

February 2024: Taylor Swift’s Biggest Reputation (TV) Easter Egg

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On the night of what people expected to be the official announcement of Reputation (TV) — aka the 2024 Grammys — Swift walked the red carpet wearing, arguably, the biggest Easter egg of all: a long white gown accessorized with all-black everything else.

Considering the cover of the original 2017 album resembled a newspaper in all black and white, and the singer changed her profile pics for all her social accounts to the same (lack of) color scheme on the same day, this case feels open and shut.

February 2024: Taylor Swift’s Super Bowl Style

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To round out her rookie season as part of Chiefs Kingdom — at the Super Bowl, no less — Tay showed her support for Kelce with a ‘fit that had multiple nods to him and his team.

This included, but was not limited to, a Judith Leiber football clutch customized with his number, 87; a Stephanie Gottlieb varsity pendant with the same insignia; a WEAR by Erin Andrews bomber jacket with the number 60 (the year the team was founded); plus a collection of red and gold jewelry.

One such standout was a ruby stretch bracelet by SHAY, which Sarah Chapelle of @taylorswiftstyled said was a whopping $19,950.

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