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.

Lais Borges/Elite Daily; Getty Images

Over the past 16 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, Swift is a style shapeshifter and she knows it.

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 blonde curls, cowboy boots, and sweet disposition, the singer-songwriter soon became a household name. However, as time progressed, Swift 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 eight 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 await Swift’s upcoming Midnights eradropping on Oct. 21 — take a look at Taylor Swift’s style evolution from 2006 to now.

2006: Taylor Swift In a Sundress & Cowboy Boots

Denise Truscello/WireImage/Getty Images

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

Rick Diamond/WireImage/Getty Images

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

Frazer Harrison/Getty Images Entertainment/Getty Images

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

Frazer Harrison/ACM2009/Getty Images Entertainment/Getty Images

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

Skip Bolen/WireImage/Getty Images

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

Jeff Kravitz/FilmMagic, Inc/Getty Images

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

Jason Merritt/TERM/Getty Images Entertainment/Getty Images

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

Axelle/Bauer-Griffin/FilmMagic/Getty Images

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 Introduces Her Edgy Alter Ego

Daniele Venturelli/FilmMagic/Getty Images

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 Keeps It Casual In Denim Cutoffs

Nancy Rivera/Bauer-Griffin/GC Images/Getty Images

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 Looks Romantic In Ruffles

Frazer Harrison/Getty Images Entertainment/Getty Images

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 Is Vibrant In Versace at the VMAs

Axelle/Bauer-Griffin/WireImage/Getty Images

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 Has a Floral Folklore Moment

Kevin Mazur/Getty Images Entertainment/Getty Images

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 Wears the ‘All Too Well’ Power Suit

Dimitrios Kambouris/Getty Images Entertainment/Getty Images

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 Pays Tribute to the 2009 VMAs

Dia Dipasupil/Getty Images Entertainment/Getty Images

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.