Taylor Swift’s Mesmerizing Fashion Evolution, Unveiled from 2006 to the Present.

Taylor Swift’s Mesmerizing Fashion Evolution, Unveiled from 2006 to the Present.

Decoding the Allure: Taylor Swift’s Mesmerizing Fashion Evolution, Unveiled from 2006 to the Present

Taylor Swift's musical eras through the years

From Madonna to Lady Gaga, a great many musicians are known for shifting their style over time to mirror their sound. Still, few pop stars have managed to pull off the sheer number of sonic and sartorial eras as has Taylor Swift.

Over the course of her decade-and-a-half-long career thus far, Swift’s gone from country sweetheart to global pop superstar, experimenting with different musical genres and proving herself to be a true style chameleon along the way.

Swift has a lot going on at the moment; in addition to her internet-breaking romance with Kansas City Chiefs tight end Travis Kelce, she’s also preparing to take her massive Eras Tour abroad, treating fans lucky enough to have scored tickets with a hits-packed setlist and sparkling costumes that nod to the many aesthetics she’s explored through the years.

Oct. 27 also marked the release of the Grammy winner’s “1989 (Taylor’s Version),” the re-recording of her chart-topping 2014 album that sealed her crossover from country to pop.

Read on for a comprehensive explainer of the styles that correspond with each of her album cycles so far, from the wild curls and dress-and-cowboy-boot combos of her 2006 debut LP to the ’70s-influenced knit polos and corduroys of 2022’s “Midnights.”

Taylor Swift (2006)

Taylor Swift 2007 Academy of Country Music New Artists' Party for a Cause
Swift wears BCBG Max Azria at the 2007 Academy of Country Music New Artists’ Party for a Cause.Getty Images
Taylor Swift 2007 Academy of Country Music Awards All-Star Jam
Swift wears a white strapless dress trimmed with feathers at the 2007 Academy of Country Music Awards All-Star Jam.Ethan Miller

When Swift first hit the scene as a teen, sweet sundresses and cowboy boots were her signature — not to mention those tight blond ringlets. Her youthful, relatable looks befit her lovestruck lyrics and status as an up-and-coming country darling.

“I get so excited about [awards shows] because I love to dress up. But I wear cowboy boots so that when I walk down the stairs I won’t fall,” Swift told Entertainment Weekly in 2007 of her practical (and genre-appropriate) Western footwear.

Fearless (2008)

Taylor Swift 2008 Grammys
Swift wears Sandi Spika at the 2008 Grammys.Getty Images
Taylor Swift 2009 CMA Awards
Swift wears Reem Acra at the 2009 CMA Awards.FilmMagic

Swift embraced fairytale fashion full on during her “Fearless” era, incorporating ballgowns, corseted bodices, tulle-skirted styles and sequins aplenty into her wardrobe; she even sang of her love for “glitter and sparkly dresses” during her “Saturday Night Live” monologue in 2009.

Along with picking pieces fit for a princess, the singer-songwriter also began swapping her cowboy kicks for sleeker riding boots and heels, in a move that foreshadowed her crossing over from country to pop.

Speak Now (2010)

Taylor Swift Speak Now tour
Swift wears Susan Hilferty during her “Speak Now” tour in 2011.WireImage
Taylor Swift 2011 Billboard Music Awards
Swift wears Elie Saab at the 2011 Billboard Music Awards.Getty Images
Taylor Swift 2011 Academy of Country Music Awards
Swift wears Elie Saab Haute Couture at the 2011 Academy of Country Music Awards.Christopher Polk/ACMA2011

The sparkles and fairytale touches continued into Swift’s “Speak Now” era, with the star stepping out in more sophisticated styles on the red carpet.

In addition to plenty of purple-hued looks that nodded to her album art, this period also marked the start of Swift’s love affair with red lipstick, which continues to this day.

Red (2012)

Taylor Swift Red Tour
Swift wears a Marina Toybina top and Bleulab shorts during her “Red” tour in 2013.Kevin Mazur/TAS
Taylor Swift navy vintage dress
Swift wears vintage at her “Red” album release party with Target in 2012.FilmMagic

From prim collared shirts paired with high-waisted shorts to pearls teamed with tea-length dresses nipped in at the waist, this was what Swift affectionately dubbed her “‘50s housewife” era.

Many of her vintage-influenced ensembles around this time stuck to a classic color palette of black, white, navy and — what else? — red.

1989 (2014)

Taylor Swift 2014 iHeartRadio Music Festival
Swift wears Jessica Jones at the 2014 iHeartRadio Music Festival.WireImage
Taylor Swift wearing a gray crop top and skirt
Swift wears Alice + Olivia in New York in 2014.GC Images
Taylor Swift Grammys 2016
Swift wears Atelier Versace at the 2016 Grammys.FilmMagic

“Welcome to New York,” indeed. The release of Swift’s fifth studio album — and her first pure pop LP — came shortly after the songstress moved to Manhattan, chopped her long hair into a chic shoulder-grazing bob and overhauled her entire wardrobe to suit her new high-fashion hometown.

Matching crop top-and-skirt sets became Swift’s new everyday uniform, almost always accessorized with sky-high designer heels. Even when she was simply leaving the gym, the star always looked perfectly put-together.

Reputation (2017)

Taylor Swift Reputation tour
Swift wears Jessica Jones during her “Reputation” tour in 2018.Getty Images for TAS
Taylor Swift Met Gala 2016
Swift wears Louis Vuitton at the 2016 Met Gala.Getty Images
Taylor Swift Balenciaga hoodie
Swift wears Balenciaga in New York in 2018.GC Images

I’m sorry, the old Taylor can’t come to the phone right now. Released roughly a year after Swift’s “Bad Blood” with Kanye West and Kim Kardashian boiled over, “Reputation” brought the musician’s most dramatic style shift to date.

Dark colors dominated this era, with an edgier-than-ever Swift opting for hoodies, combat boots, cargo pants, camouflage patterns and jet-black sequins. And months after Kardashian labeled the singer a snake on social media, Swift reclaimed the slithery symbol by sporting snakeskin prints and serpentine jewelry aplenty.

Lover (2019)

Taylor Swift wearing tie-dye

Both musically and sartorially, Swift stepped back into the daylight with “Lover,” trading snakes for butterflies.

Gone were the moody hues of her “Reputation” days, replaced with sugary sweet pastels, dreamy tie-dyed separates and plenty of sparkle to match her new album’s bubblegum sound.

Folklore/Evermore (2020)

Taylor Swift Folklore
Taylor Swift Evermore album art
Taylor Swift Grammys 2021

Can you say “cottagecore?” Surprise-dropped during the COVID-19 lockdown, Swift’s duo of critically acclaimed “sister albums” saw her paring back the production and placing more focus than ever on storytelling, all while dressed in cozy outfits fit for curling up by the fire (or going for a walk in the woods).

Countryside-ready plaid coats, rich velvets, ditsy florals and chunky knit sweaters — the lead single of “Folklore” is called “Cardigan,” after all — defined this era from a style standpoint, with Swift forgoing her sleek blowouts and styling her natural curls in softly braided buns.

Midnights (2022)

Taylor Swift VMAs 2022
Taylor Swift 2022 American Music Awards.
Taylor Swift 2023 Grammys

She can still make the whole place shimmer. When Swift made a surprise appearance on the VMAs 2022 red carpet dripping in crystals (courtesy of Oscar de la Renta), fans suspected a new era was afoot — and the musician confirmed it during the ceremony, announcing her 10th studio album was on the way.

Aesthetically, Swift’s “Midnights” era has been steeped in ’70s flair, from the knit polos, corduroy pants and blue eyeshadow she sported for the album artwork to the glitzy, glittering, Studio 54-worthy looks she’s been wearing on recent red carpets.

When Swift said she’s a mirrorball, she didn’t lie

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