The Trajectory of Taylor Swift, As Told By Her Outfits

Grab your six closest friends and a calculator, it’s time to analyze.


Today, Taylor Swift turns 27. That puts us five years past the unproblematic anthem that was “22,” if you trust my calculus. She’s been famous for so long that it’s hard to remember a time when she wasn’t. But to forget the teardrops on her guitar is to forget her roots!!! To understand New Edgy Taylor, we must first seek to understand Ernest Nashville Taylor — and I feel it’s my civic duty to unpack this narrative. I’m going to do it through her clothes, because her style evolution perfectly dovetails with her transition from country teen queen to the leader of the proverbial cheer squad and it’s very satisfying.

Shout out to Taylor for putting out an album every two years for the past decade because it made this extremely easy for me. Turn on some T Swift please.

2006: Earnest Nashville Taylor


AOL keywords: tight messy curls + empire waist dresses + cowboy boots

Soundtrack: Teardrops On My Guitar from Taylor Swift

Earnest Nashville Taylor didn’t tame her hair because that would have been way too ~mainstream~ for a girl next door such as herself. She wore midi-length handkerchief hemlines almost exclusively (innocence & 2006) and her biggest problem was making sure some dumb teen boy remembered that her favorite song was by Tim McGraw. ENT occasionally verged on hippy because her stylist (possibly just her?) wasn’t overly focused, which was a perfect reflection of her unmanaged image at the time. ENT was a hopeless romantic which comes through in her shoulder-y poses. Black eyeliner because high school.

2008: Country Royalty Taylor


AOL keywords: 1/4 curling iron + romantic dresses + as much beading as fucking possible

Soundtrack: Forever and Always from Fearless

Country Royalty Taylor had her romantic innocence dial turned up to 11 because she’s smart and that shit was marketable. Bonus style points were awarded when people compared her to a young Faith Hill. Her dresses during this era call to mind a young girl obsessed with princesses and Joe Jonas and maybe Texas, but like, modern Texas. They were nipped in at the waist as a wink at sexuality. Her hair stayed curly — couldn’t betray the OG fans — but on the DL it was actually dried straight and then re-curled with the thinnest of curling irons.

2010: Pure & Polished Taylor


AOL Keywords: pale palette + chiffon + coifed as fuck

Soundtrack: Enchanted from Speak Now

Pure & Polished Taylor is playing two games: on-duty royalty who just might drink you under the table and then deny it the next day. Her color palette was subdued and virginal, her fabrics were romantic because her heart was V. much broken (by John Mayor in particular). PPT marked Taylor’s first foray into hair straightening. This was a little blasphemous to Earnest Nashville Taylor, but also a true industry-straddling moment. The world needed to be poised for…

2012: All-American Red Hot* Taylor


AOL Keywords: hot pants + Keds + red lipstick

Soundtrack: We Are Never Getting Back Together from Red

All-American Red Hot Taylor signified a successful leap to pop music, what with all the hot pants and fedoras. But safe pop. There was red lipstick and dark sunglasses and freshly brushed ponytails. It all felt very coifed ’50s-style sweetheart with a wild streak to appeal to young girls, Harry Styles and creepy dads alike. Great for album sales. AARHT wore high-waisted shorts with Keds sneakers for two years straight and not a single person complained, including me. Her colors were red, black, white and yellow almost exclusively, conjuring patriotism and exuberance.

*like the candy, Happy Holidays!

2014: Sexy Squad Leader


AOL Keywords: crop top + high heels + spray tan + dirty blond lob

Soundtrack: Welcome to New York from 1989

AARHT primed the world for Sexy Squad Leader, paving the way for Taylor to go full-pop without public backlash. SSL wasn’t afraid of a thigh high boot nor a spray tan, because her newfound feminism gave her the confidence to wear what she wanted. Like thousands, maybe millions, of crop tops. She had just as many very close female friends. SSL was given the title of Global Welcome Ambassador for NYC Tourism, which made a lot of New Yorkers groan but probably brought a lot of money to the city so whatever! Maybe the L will start running faster. Thanks Tay.

2016: New Edgy Taylor


AOL Keywords: high slits + platinum bob + chokers 

Soundtrack: Don’t Wanna Live Forever, feat. Zayn, 50 Shades Darker

New Edgy Taylor doesn’t give a fuck what you think (but maybe she does, because don’t we all)? NET is bold in her deviation from her now-signature red lip and is not afraid of bronzer. She wears chokers only because anything longer would be too romantic and she doesn’t have time for that shit anymore. Her color palette is bold and severe because softness is so Pure & Polished Taylor and she’s over it. Heels are still high but not for long, if you ask me. The trajectory is long but it’s linear: I’m keeping my eyes peeled for Converse and T-shirts in 2017. Mark my words: Downtown Taylor is coming for us.

If you see her, wish her Happy Birthday for me!

Photos via Getty Images.

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  • Quinn Halman

    I miss the old T-Swift, straight from Nashville T-Swift
    Acoustic guitar intro T-Swift, quick change at her shows T-Swift
    I hate the new T-Swift, the smokey eye T-Swift
    The always squinting T-Swift, boyfriends making news T-Swift
    I miss the sweet T-Swift, cowboy boots tapping to the beat T-Swift
    I gotta say, at that time I’d like to meet T-Swift
    And now I look and look around and there’s so many T-Swifts
    I used to love T-Swift, I used to love T-Swift
    I even had the “13” on my hand, I thought I was T-Swift

    • Lillian

      I love this shit

    • Haley Nahman

      Did you just write this quinn, who are you

      • Quinn Halman

        yes, despite having a final tomorrow I did reappropriate a Kanye song to be about Taylor. There is nothing I cannot do.

    • prairie_dogs

      You need a pulitzer for this.

    • courtforce

      o… m… g… thank you!

    • Natty

      omg, this is everything i didn’t know i needed

  • Andrea Raymer

    Taylor. It’s been 2 years. I need an album. How am I supposed to know what emotions I am feeling without one?

  • THIS WAS SO COOL. I’ve never been so interested in t.swift my entire life. Thank you, Hailey.

  • Samantha Lee

    Haha, love this. You’ve got her style evolution down to a T.

    • Haley Nahman

      Down to a T Swift??

      • Samantha Lee

        Touché. Touché

  • Iiinat

    Can someone please do a post soon on what to wear for New years eve? I am going to my first party for years and are freaking out! Where do i find what to wear? Will it arrive in time? What if there is no dress code?

    • Haley Nahman

      I believe one is coming!!

  • Nikelle

    Oops “sexy square leader” replaced squad in copy! Loving the AOL keywords in pure and polished and country royalty.

    • Ashley Flores

      ‘Square’ leader is more accurate, leave it ha

    • Haley Nahman


  • tmm16

    2006: Earnest Nashville Taylor was my fav T Swizzle. Her original, “country” hits got me through many crushes. I would play “Teardrops on My Guitar” through my red chocolate Verizon phone and think of Nate in 7th grade. Good times! #TaylorsRule

  • Alexandra

    Also to be noted was the Great Post-Kanye Conflict Divide — when Taylor’s latent Clausewitzian outlook ossified into what now rivals that of both Beyonce and Henry Kissinger.

    • Yue

      Underrated comment. I feel about taylor almost like I feel about henry kissinger (well, if you exclude all his war crimes, which is why “almost”)

  • Jessica

    Thanks, Haley. Currently sending this to all my friends. T-Swift (public persona) is such a case study for me.

  • doublecurl

    oh my god your first mention of ENT is “Ernest Nashville Taylor” which is totally first name Ernest middle name Taylor and I LOVE it

  • whydontYOUpickYOURusername

    Converse and tees in 2017? YES PLEASE! So ready for 2017 Out-n-Proud KStew-Inspired Blazers-N-Jeans Tay. (Or 2018. I can wait.)

  • Qamar Shehzad

    Taylor Swift are breathtaking for the beauty of Women. They are looking ideal in long length Apparal. These photos are extremely loving. Hence, patterns are cool and visionary. Post shows great designs with strong stuff. Sexy Squad Leader is high-end.
    Regard: Qamar

  • For someone that’s had to grow up in the spot light I think she’s done a grand job of maintaining her brand image, developing with the times whilst keeping a touch of the personal edge that makes her accessible and the Taylor that people adore. She’s pretty rockin, I think!


  • her style is better each day, love Taylor

  • Mary

    Can you do this with Beyonce??

  • Of all Taylor fazes, I myself was inspired by “We are never ever getting back together” bangs and red lipstick 💋

  • 2010 and 2016 for me please. Her little red riding hood period was like going back for me, and only one more thing: We have already seen her in converse!

    Find out my favourite over the knee boots to go shopping.

    Have a lovely day! MG

    • I am so checking them out. I’ve been searching for the right ones for a while… I am so picky on this I think I might find them until summer. Lol

  • prairie_dogs

    This reminds me of something that Vogue used to do with some of its cover subjects– there’s this incredible mid 2000’s rundown of Gwyneth Paltrow’s event looks (and famous boyfriends!) from the 90s on, that accompanied a cover article about her. Clearly it made an impression, because I thought of it as soon as I read this. Anyway, I LOVE this concept, and it was awesomely researched, and I would read lots more articles like this. 🙂

  • I think everyone has a similar phase… analyzing “clothing careers” over the years is extremely interesting not only for TS.

    For example : INTENSE – clothing careers – Beginnings ( and you can search them for the “now” phase lol ) :

    Bryan Boy ( Before )

    Arielle – Somethingnavy ( Before )

    Can someone please explain how did this happen.
    HUG to everyone and awkard starts. Cause, Who doesn’t have them?

  • oliviafortune


  • Hope