Taylor Swift's Eras Explained: A Look at Her Style Evolution From 2006 to Now

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Since the age of 16, Taylor Swift has been releasing music that has helped people with every emotion in spades. With the lead-up to her highly anticipated tour in 2023, fans have been taking a deep dive into all her beloved eras, from country princess to a glitzier pop star. Every artist goes through style changes throughout their career, but Swift has proven time and time again that she is anything but average. With each album, she meticulously crafts an aesthetic to pair with them. This not only includes the cover art, but her Instagram layouts, red carpet ensembles, tour looks, and music video choices. In Swift's world, there's no such thing as leaving things less than perfect. Despite the past notions of her being "boy-obsessed" or "vindictive", there is only one way I'd describe her—a devoted artist. 

Swift first came onto the music scene in 2006 with fiery curly hair, cowboy boots, and a guitar always in tow. Her latest album, Midnightsconsists of celestial dreams. Think jewel-encrusted dresses, metallic eye makeup, and plenty of revenge dresses. Along the way, bold red lipstick was a signature touch she kept all the way through.

In honor of her upcoming tour, we're taking a look back into every era part of Swift's career. If you were lucky enough to get tickets, you might even get inspired to figure out your concert look. Do you resonate with the cinematic lyrics and homey cardigans of Folklore? Or the revenge-ridden and angsty touches of Reputation? Keep scrolling to take a look.

Taylor Swift, 2006

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When Taylor Swift first came onto our radar, her style was very country girl meets boho. Along with her blonde curls, this era was eponymous with sundresses and cowboyboots.

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Fearless 2008

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While Swift was still holding onto her beloved cowboy boots, the release of Fearless sparkled a stylistic journey for the artist. With her debut concert tour came a lot of glitzy dresses embellished with sequins and fringe galore.

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Speak Now, 2010

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With songs like "Enchanted" and "Sparkly Fly" on the album, Speak Now brought whimsical and fairytale elements to music and style. Her concert looks were filled with sweetheart necklines and tulle dresses while her off-duty ensembles featured oxfords and frilly blouses. She was almost always seen in a bright red lip, which has been her signature choice of makeup since.

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Red, 2012

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2012 was the year of the "hipster" and "twee" style, and Swift was very clearly on trend. Her Red era consisted of striped and polka dot sweaters, ballet flats, and of course, various shades of red. Released in October, it is an ideal fall album. (Especially after you put on your thick knit scarf and listen to the 10-minute version of "All Too Well".) 

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1989, 2014

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As an album, 1989 was a distinct shift from the music she started with. She's often described it as cutting ties with her old-country self, and her style during this era sends the same message. Gone are the days of frilly dresses, and in are snazzy crop tops and high-waisted shorts. 

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Reputation, 2017

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Everyone has their "goth" era, even Taylor Swift. Her style shifted from lively to dark with all-black ensembles and burgundy lipstick to replace her usual penchant for bright reds. On tour, she kept moody tones with snake motifs, grunge knee-high boots, and black sequined bodysuits. To phrase "Look What You Made Me Do", the old Taylor can't come to the phone right now—because she's dead.

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Lover, 2019

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Swift's moody era didn't last very long, as she traded in the all-black looks for dreamy pastels when she released Lover in 2019. Her style became all about rainbows, frills, and in true Swift fashion—glitter. While Reputation was an album for revenge, Lover was an ode to joy.

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Folklore and Evermore, 2020

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Folklore and Evermore were true quarantine albums, and despite there not being many style moments spotted during this time, it was clear from the album art that coziness and comfort were the intended look. "Cottagecore"

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Midnights, 2022

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Released this past October, Swift's Midnight's era is precisely how it sounds. Taking celestial inspiration the star's recent looks have been filled with plenty of metallics and disco-ball-inspired pieces. 10 albums later and she's still brought out the glamour in full force. (We expected nothing else.)

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Next, The 17 Celebrity Outfits of 2022 That Will 100% Go Down in Fashion History

Assistant Market Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.