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Taylor Swift - May 2006

Taylor Swift Fashion History

I BELIEVE Taylor was 16 in this picture, and just coming onto the scene. Boy are these days long gone, but then, you think about all the 16-year olds now who are in skintight sequined minis and this just seems so refreshing and REGULAR and breezy and She's Not Gonna Grow Up Too Fast and whatnot.

Taylor Swift - November 2006

Taylor Swift Fashion History

This is a little Misguided Vixen.

Taylor Swift - April 2007

Taylor Swift Fashion History

This is totally appropriate also for what a teenager would wear to one of these things -- right down to shoes that are TRYING to be cute but instead are just sensible to the point of being ugly. Somewhere in her life Taylor became synonymous for me with blush sequins, fair or not, and I suspect this is where it started.

Taylor Swift - April 2007

Taylor Swift Fashion History

The Lord of the Rings: Nymph Prom.

Taylor Swift - May 2007

Taylor Swift Fashion History

Remember when she and custom cowboy boots? She will NEVER EVER wear those again, EVER, I suspect. I'd actually love it if she wandered out of the gym in those next week.

Taylor Swift - May 2007

Taylor Swift Fashion History

This feels very much like what your standard blonde country singers wore to these things in 2007. And also possibly today.

Taylor Swift - November 2007

Taylor Swift Fashion History

THIS Disney princess rolls in the hay with abandon.

Taylor Swift - February 2008

Taylor Swift Fashion History

Oh my sweet pickles. NO. Even David's Bridal would be like, "Wha-aaat?"

Taylor Swift - May 2008

Taylor Swift Fashion History

But THIS is major. I think getting to go to the Met Gala was actually something of a turning point for her, tackyness-wise.

Taylor Swift - May 2008

Taylor Swift Fashion History

This is just lovely. One of her best looks, actually.

Taylor Swift - fall 2008

Taylor Swift Fashion History

Hark, this is from Olden Tymes when people wore dresses to these things and not simply belted boobs or hot pants. (I still don't like her shoes. The giant thick straps feel so geriatric to me.)

Taylor Swift - November 2008

Taylor Swift Fashion History

That's good, though -- that's her Met Gala training in action as well, I think. She's learning to go slinkier and more grown-up at this point.

Taylor Swift - November 2008

Taylor Swift Fashion History

But then she wore this dress, which I think is in the middle of shedding its skin.

Taylor Swift - February 2009

Taylor Swift Fashion History

A MUCH better foray into black than the one from early in the slideshow, but it does feel discordant on her, doesn't it?

Taylor Swift - February 2009

Taylor Swift Fashion History

I just wanted you to know that she's always had great taste in coats.

Taylor Swift, Miley Cyrus, April 2009

Taylor Swift Fashion History

Isn't THAT a walk down memory lane. Or more of a face-plant. (Taylor probably wins this, but honestly, they both look cute and youthful and appropriate for the "Hannah Montana" premiere. I love this, especially knowing Taylor will probably never go to the premiere of anything Miley ever again.)

Taylor Swift - April 2009

Taylor Swift Fashion History

First red! It has promise but it's swallowing her up a little. Maybe? I might be being too harsh, OR I just know that there's a red one coming that I love the most and so this can't stand up to it.

Taylor Swift - June 2009

Taylor Swift Fashion History

Hmm. Better for a New Year's Flappin' Eve, maybe?

Taylor Swift - fall 2009

Taylor Swift Fashion History

The makeup looks too cartoonish with this, like her face-paint gun was jammed on "WOOHOOOOO," but the dress is mostly pretty. I BELIEVE it goes sheer below the knee, but she's totally trying to marry her sparkly aesthetic with an adult one, and I appreciate the effort.

Taylor Swift - November 2009

Taylor Swift Fashion History

I think this was too samey too soon after the VMAs. It's also less appealing to me.

Taylor Swift - January 2010

Taylor Swift Fashion History

Well, it's certainly the NICEST TP job I've ever seen on a person.

Taylor Swift - February 2010

Taylor Swift Fashion History

I like the idea of this better than the execution of... whatever is happening on her torso. It's giving her tumors where there are none.

Taylor Swift - April 2010

Taylor Swift Fashion History

Hmm. I want to dismiss this for some reason, and yet -- and I equally unable to articulate why -- I also like it.

Taylor Swift - November 2010

Taylor Swift Fashion History

Why yes, I WILL buy one of those tiny ice cream cups with the wooden paddle-spoons during Intermission. Thank you, kind, foxy Theatre Service Professional.

Taylor Swift - November 2010

Taylor Swift Fashion History

Minidresses + bangs = I Want To Be Taken More Seriously Now.

Taylor Swift - November 2010

Taylor Swift Fashion History

Switching into a sleek pantsuit + bangs = No Seriously I'm 21 Now, It's ON.

Taylor Swift - January 2011

Taylor Swift Fashion History

I actively dislike that dress -- I HATE the design, with an intense burning that is scorching my esophagus into ashes - but I kind of wish the two of THEM had dated. A good song would've come from it. They could've done a he-said, she-said and DUETTED. MISSED OPPORTUNITIES.

Taylor Swift - Oscars 2011

Taylor Swift Fashion History

Granted, it's just the after party, but this is a lot more Golden Globes to me. This as her first Oscars, and tiny-and-tight FEELS too much like a rookie move there.

Taylor Swift - May 2011 Met Gala

Taylor Swift Fashion History

Ugh, what a gnarled mess. That looks like someone's ancient map of an old land war, which you are NEVER to get into in Asia, by the way. So I've heard.

Taylor Swift - November 2011

Taylor Swift Fashion History

It's pretty, but doesn't it also look like the skirt is all balled up so it can forcibly expel itself?

Taylor Swift November 2011

Taylor Swift Fashion History

"Hey guys! I'm pretty sure I look cute, but I didn't REALLY try that hard, so whatever. I'm busting out of country music soon enough anyway."

Taylor Swift - Feb 2012

Taylor Swift Fashion History

Very cutesy that the dress makes a heart the same way she used to do with her hands. Like she's stamped with her own signature move. I want to redesign the top.

Taylor Swift - April 2012

Taylor Swift Fashion History

Fab. One of her best.

Taylor Swift - May 2012

Taylor Swift Fashion History

Ehhhh. I don't like that the lace underneath looks like veins. Your circulatory system is your business.

Taylor Swift - July 2012

Taylor Swift Fashion History

I am just not sure teens are choosing those shoes. Ever.

Taylor Swift - September 2012

Taylor Swift Fashion History

Here, she mostly looks like a mannequin in a Macy's window.

Taylor Swift - November 2012

Taylor Swift Fashion History

Very pretty. Another one of her best looks, I think.

Taylor Swift - November 2012

Taylor Swift Fashion History

That's really good TOO but it's a similar sort of idea. She did get into a rut sometimes.

Taylor Swift - November 2012

Taylor Swift Fashion History

It's not offensive, except in how boring it is. Burn before wearing.

Taylor Swift - November 2012

Taylor Swift Fashion History

This feels so Kendall Jenner to me, and she didn't even really EXIST yet at this time. It's SORT OF sheer and has SOME bare patches and is basically like sticking three toes onto the wild side. (If it were Kendall, it would be TOTALLY sheer with LOTS of bare patches, probably.)

Taylor Swift - January 2013

Taylor Swift Fashion History

So crisp and elegant.

Taylor Swift - January 2013

Taylor Swift Fashion History

So boring and under-styled.

Taylor Swift - January 2013

Taylor Swift Fashion History

Good, but hardly surprising.

Taylor Swift - February 2013

Taylor Swift Fashion History

It's hard to get excited when her whole posture is defensive and Over It, but I'm sure that was just... one weird photo from the night, right? It's okay. She's done worse, she's done better.

Taylor Swift - Feb 2013

This is FOR SURE worse. It's like a sumo strip.

Taylor Swift - April 2013

Taylor Swift Fashion History

But then this is sublime. She is giving me whiplash, which is a problem, as I already have vertigo right now.

Taylor Swift - May 2013

Taylor Swift Fashion History

For the Met Ball, I might actually like this and its oddities.

Taylor Swift - May 2013

Taylor Swift Fashion History

The top of that looks SO MUCH like she's on the Greek gymnastics team or something.

Taylor Swift - June 2013

Taylor Swift Fashion History

Why the hip scarves, Taylor? Don't tease us with them. USE THEM.

Taylor Swift - June 2013

Taylor Swift Fashion History

I suppose we should be impressed that she made it this far before her first Herve Leger bandage dress, which is a basic rite of passage for starlets of a lower list level than she is. However... that's actually a pretty good one.

Taylor Swift - August 2013

Taylor Swift Fashion History

I am okay with this.

Taylor Swift - September 2013

Taylor Swift Fashion History

This look tips, to me, toward the Casualwear Taylor Swift we've come to know in 2014. It has a very vintage feel to it.

Taylor Swift - November 2013

Taylor Swift Fashion History

Perfection. It's wonderful.

Taylor Swift - November 2013

Taylor Swift Fashion History

THUD. She is the crabbiest video vixen at the reunion.

Taylor Swift - November 2013

Taylor Swift Fashion History

"I'm not saying Harry is available but he DOES love blondes."

Taylor Swift - January 2014

Taylor Swift Fashion History

I don't really love the cut of this dress - nor her hair, actually - but this isn't a total mess and felt like an auspicious start to her red-carpet year.

Taylor Swift - Jan 2014

Taylor Swift Fashion History

And this totally harshed my buzz. I said at the time that it resembled a drunken hammock and I stand by that.

Taylor Swift - Feb 2014

Taylor Swift Fashion History

Another one of my all-time favorites. Gorgeous and classy.

Taylor Swift - March 2014

Taylor Swift Fashion History

And then... a big WHATEVER. Hard to muster up a feeling.

Taylor Swift - April 2014

Taylor Swift Fashion History

I DO remember liking this, though. It's flirting with the boundaries of what i consider the acceptable midriff amount, but she's carrying it with a lot of dignity.

Taylor Swift

Taylor Swift Fashion History

A rare "meh" for me from Oscar de la Renta.

Taylor Swift

Taylor Swift Fashion History

I just never felt like anything happening in the back ever did itself justice, and the front wrinkled up terribly, and... there was so much exquisite OdlR at this gala that it's just sort of a wah-waaaah.

Taylor Swift - summer 2014

Taylor Swift Fashion History

I like this well enough for the event; it's VERY teen, but in a way that doesn't make her look delusional for wearing it.

Taylor Swift - August 2014

Taylor Swift Fashion History

Perfectly fine; fancy and serious for a movie premiere, but not so dramatic that she's trying to hijack the night from the people who had larger parts.

Taylor Swift - September 2014

Taylor Swift Fashion History

AND THEN THIS. I hated it then; it makes me laugh now. I still think it looks ridiculous, especially with those shoes, and the pattern looks torn straight from one of those Escape This Room games where you have to find the UV torch and then shine it on the onesie to find the code for the box that has the key in it that unlocks the vent with the screwdriver in it so you can unclamp the toaster and put in the bread and read the message that takes you to the place where you throw the globe in the fire and then there's a puzzle piece to stick in the door and OOPS THERE ARE ELEVEN MORE TO FIND.

Taylor Swift - September 2014

Taylor Swift Fashion History

Another pretty good execution of the midriff trend. It helps to have her exact midriff, obviously.

Taylor Swift - November 2014

Taylor Swift Fashion History

This, though, I really hated. It is so uninspiring.

Taylor Swift - December 2014

Taylor Swift Fashion History

Sure! She seems skeptical, and her chest might not be comfortable, but I've seen worse.

Taylor Swift - December 2014

Taylor Swift Fashion History

That I actually don't hate, either, despite the "Jolie Museum of Thigh in Leg City" of it all.

Taylor Swift - December 2014

Taylor Swift Fashion History

So, so pretty.

Taylor Swift - Dec 2014

Taylor Swift Fashion History

Just crazy enough to work.

Taylor Swift - December 2014

Taylor Swift Fashion History

Just J.Lo enough to hurt.

Taylor Swift

Taylor Swift Fashion History

Just Reese Witherspoon enough for it to make good sense that I have more slideshows coming later this week of BOTH of them.

Taylor Swift: A Red-Carpet Fugstory
This was the year Taylor Swift took a very large step into the fashion spotlight, largely due to her habit of waltzing out of nondescript New York City buildings looking as perfect and polished as if she were leaving her stylist. But we'll take a look at her casual clothes later; she's also come pretty far on the red carpet from her humble booted beginnings, and that's a fun evolution to see. Enjoy. *Note: We're having weird issues with our slideshows occasionally wherein only half the title shows up, cutting off the date of the outfit in question. While this is getting fixed on our end, you can see the complete title if you refresh the page. [Photos: Getty, Splash, Fame/Flynet]

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