A Complete History of Taylor Swift's Style

In which we analyze the singer's many looks, album by album.
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Eliza Brooke
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In which we analyze the singer's many looks, album by album.
Swift at a recent concert. Photo: Christopher Polk/Getty Images

Swift at a recent concert. Photo: Christopher Polk/Getty Images

In case you missed it, Taylor Swift's latest album has dropped.

Since the video for "Shake It Off" hit YouTube in August, we've known that "1989" would be a major departure musically, marking a transition from sorta country to pure, heady pop. Music critics and the Internet at large have been scrutinizing the album since it went live at midnight, and bravely so.

But this is also a great moment to talk about Taylor Swift's style evolution, because it matches up so well with her discography. You can effectively break down Swift's history of wearing clothes as a famous person into distinct periods bookended by sequential album drops. So we went and did that. 

We give you the album-by-album history of What Taylor Wore, unabridged. Except there are no photos of her cat. Sorry.

Taylor Swift

Dominant themes: Disney princess influences, cowboy boots, very curly hair.

When Swift broke onto the music scene with her eponymous debut album in 2006, she was the teenagiest teenager imaginable. She was 16 years old, singing about unrequited high school love and sneaking out late, so it follows that her wardrobe primarily comprised things you might find at a junior prom.

Swift led her likability campaign in a series of babydoll dresses with spaghetti straps. At awards shows she went for long gowns with a princessy vibe. Notable examples include a purple corseted deal with flowers running down the skirt, a gathered yellow situation reminiscent of that one dress from "Beauty and the Beast" and a black satin dress she paired with elbow-length black gloves, an "iconic" look according to Seventeen's prom issue.

Because "Taylor Swift" was the singer's twangiest, most country album -- see references to Chevy trucks gettin' stuck on back roads at night in "Tim McGraw" -- cowboy boots figured heavily into her stage performances. Her mane of curly hair gave her an unprocessed girl-next-door vibe. 

Fearless

Key elements: Lower cuts, elegant necklines, sequined fringe, looser curls.

With the November 2008 release of "Fearless," Swift was growing up and setting out on her first headlining tour. Her competitive nature emerged in the song "Change," which focused lyrically on beating the odds and #winning. The proceeds from the song were donated to the U.S. Olympic team, which had recently competed in the Beijing summer games.

To complement this stronger, fiercer stance, Swift began going for more mature, streamlined gowns at events -- deep v-necks and strapless sweetheart necklines abound during this period. For more casual affairs, pretty but unembellished A-line chiffon dresses and body-conscious minis took the lead. Swift also began to loosen her curls during this period, often going for a romantic low bun.

With a little less adornment, cleaner necklines and updos that showed off her elegant frame, Swift made herself the center of attention. In other words, she was wearing the dress -- not the other way around.

"Love Story," Swift's "Romeo and Juliet"-inspired hit, drove a few of her tour costumes toward the Ren Faire end of the princess spectrum, but for the most part the singer favored sassy shift dresses with metallic fringe. These Swift paired with boots, as she had in earlier years, but not cowboy boots. With "Fearless," Swift had begun to distance herself from her country roots. 

Speak Now

Dominant themes: A lot.

"Speak Now," released in October 2010, kicked off the most varied sartorial period of Swift's career. The 20-year-old hung on to the gauzy, romantic gowns and sweetheart necklines that had become a familiar part of her wardrobe, but also pushed into vintage-inspired territory with pinup-style halters and twee little dresses that could have been borrowed from Zooey Deschanel's closet. Just before "Red" dropped, Swift got blunt bangs, started flat-ironing her hair and began embracing sexier dresses. 

Essentially, Swift was figuring herself out, trying on different identities like any other college-age kid. That same not-a-girl-not-yet-a-woman confusion manifests in the album. In "Never Grow Up" and "Innocent," Swift is reluctant to give up the safety of youth ("Wish I'd never grow up / I could still be little") but draws prematurely on the challenges of adult love in "Mine" ("We got bills to pay / We got nothing figured out"). But then the singer turns around to show an entitled, wild-eyed immaturity in "Better Than Revenge" and "Speak Now," a song in which she fantasizes about breaking up an imminent marriage at the last moment.

Those conflicting impulses show. The girlishness of the full-skirted Manic Pixie Dream Girl looks; a not-entirely-convincing sexiness shown in a few sequined, body-con minidresses. 

Red

Dominant themes: Flat-ironed hair, strategic skin, '50s-style dresses, accessible hipster wear.

Swift's style during "Red," while decisive and well thought-out, was an exercise in contrasts, particularly when it came to dressing for events. In opposite corners we had Sexpot Taylor, smoldering behind heavy bangs, and Kennedy Aspirant Taylor, with her conservative dresses and red lipstick.

Regulation Hottie Taylor wore a lot of sleek dresses in black or white with cutouts and daringly low necklines. Bedazzled mini dresses like the kind you'd see at the club also made a few appearances; notably, Swift wore one such look to perform at the Victoria's Secret Fashion Show, looking very much like a VS Angel herself. The beauty look here focused on a smoky brown eye and flat-ironed hair. 

Retro Taylor, on the other hand, was all about a clean cat eye, a red lip and full-skirted, boat neck dresses that your grandmother would approve of. And by that, we mean that Conor Kennedy's grandmother would approve of. Swift was dating Kennedy while working on "Red" and based the song "Starlight" on a photo of Ethel and Robert Kennedy from the late 1940s. Not hard to see where the inspiration for these looks originated.

I know: Those two personas are so opposite! It's crazy. But women contain multitudes, so here's one more identity to add to the list: Taylor on Tour. 

The Red Tour was the first of Swift's that had a strong, cohesive costuming theme. It started with the album's cover art: The hat, the white shirt and that red, red lip. From there, Swift added in some striped tops, oxford shoes, porkpie hats and high-waisted short shorts. The look brings to life that line from "22" about how "it feels like the perfect night to dress up like hipsters / and make fun of our exes." Taylor's very cleaned-up take on hipsterdom has the sort of old-timey-ness that makes you want to give her a mug with a mustache painted on it for her birthday. 

1989

And here we are, friends. The present day.

The "1989" period effectively started with Taylor's shoulder-length cut. Thus far, the dominant elements are bright colors and crop tops with kicky skirts -- she has, after all, started going to the gym with Karlie Kloss a lot, so now's probably the time to show the abdominals. It's the wardrobe of a pop star.

Re: the abundance of crop tops, the important thing here isn't that she's wearing them. It's that she jumped on the trend way late. That's because Swift isn't -- has never been, if you look back at those babydoll dresses from '06 -- a forward thinker when it comes to fashion. She's mainstream. In fact, Swift goes out of her way to play up the fact that she's not especially cool in order to make herself more relatable. Just take a look at all the awkward dancing in the video for "Shake It Off."

There's also a new man repellence to her outfits, best exemplified by that unexpected, absurd and amazing Mary Katrantzou bodysuit she wore to the VMAs. Taylor is single and loving it. Taylor lives in New York, city of weirds. Taylor spends all her time with her independent-minded girlfriends. So Taylor's dressing accordingly. As she told The Guardian recently, she's not trying to be cool, and she's not aiming to be a sex symbol.

The Mary Katrantzou look was provocative in its lightheartedness, and, following on the heels of her single "Shake It Off," did a fantastic job driving home the message that Taylor Is Done Giving a Shit About What You Think. Haters gonna hate hate hate hate hate, basically.

Even her hair is a little good-weird now, with that floppy Mick Jagger cut. In the "Red" era, Swift learned how to work her babeliness, sometimes taking it a little far; with "1989," the singer knows she's hot, but she's having way more fun with her styling. 

As far as fashion mindsets go, that's something we can dig.