LOS ANGELES, CA - SEPTEMBER 07: Singer Taylor Swift arrives at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California. (Photo by Frederick M. Brown/Getty Images)
This is all very ideal for a 19 year old in 2008. She was squeaky-clean and just crossing over from country, and she was never going to dive straight into insanity. This outfit says, "I'm getting the lay of the land." That bracelet says, "Heather, COME AND FIND ME."
In 2009
NEW YORK - SEPTEMBER 13: Singer Taylor Swift arrives at the 2009 MTV Video Music Awards at Radio City Music Hall on September 13, 2009 in New York City. (Photo by Michael Loccisano/Getty Images)
This more direct attempt at glamour feels like it's too formal for the VMAs. It's neither outrageously glam enough, nor wacky enough. So while she looks nice, it's almost like she was burning it off because otherwise it had to go back -- like realizing you didn't read your library book until the day before it's due. And is what she was wearing when Kanye stormed the stage, and she could NOT have scripted THAT better, because it underscores the sense of him barging in on the innocent young thing.
In 2009
NEW YORK - SEPTEMBER 13: Taylor Swift poses in the pressroom during during the 2009 MTV Video Music Awards at Radio City Music Hall on September 13, 2009 in New York City. (Photo by Michael Loccisano/Getty Images)
This is the sequel to 2008, really. (I thought this was what she had on for Kanye originally because I saw her holding a trophy in this, but ... she won several, I think, so OH WELL.)
In 2010
LOS ANGELES, CA - SEPTEMBER 12: Singer Taylor Swift performs onstage during the 2010 MTV Video Music Awards at NOKIA Theatre L.A. LIVE on September 12, 2010 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
So of course, the next year was when Taylor got up on-stage and sang a humorless ballad all about how deeply an immature person wounded her. This was, I think, the beginning of Taylor starting to take herself very very very seriously (not that she wasn't entitled to be annoyed by Kanye, however).
LOS ANGELES, CA - SEPTEMBER 12: Singer Taylor Swift performs onstage during the 2010 MTV Video Music Awards at NOKIA Theatre L.A. LIVE on September 12, 2010 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
I mean. Barefoot and brooding a year later? Singing a lecture? Girl.
in 2012
LOS ANGELES, CA - SEPTEMBER 06: Singer Taylor Swift arrives at the 2012 MTV Video Music Awards at Staples Center on September 6, 2012 in Los Angeles, California. (Photo by Frederick M. Brown/Getty Images)
This was a step toward sophistication, but the hair looks too fake to me. It might NOT be fake, but it really resembles mannequin hair.
LOS ANGELES, CA - SEPTEMBER 06: Singer Taylor Swift arrives at the 2012 MTV Video Music Awards at Staples Center on September 6, 2012 in Los Angeles, California. (Photo by Christopher Polk/Getty Images)
And whether you like the pants depends heavily, I think, on the angle at which they are viewed. This one is less advantageous.
LOS ANGELES, CA - SEPTEMBER 06: Singer Taylor Swift performs onstage during the 2012 MTV Video Music Awards at Staples Center on September 6, 2012 in Los Angeles, California. (Photo by Christopher Polk/Getty Images)
This was "We Are Never Getting Back Together," and a jaunty striped shirt will certainly make a girl feel like you can tell a dude to EFF OFF. I liked this performance. It was cute and had personality that an endless parade of sparkly short skirts and bras do not.
In 2013
NEW YORK, NY - AUGUST 25: Musician Taylor Swift (Detail: Herve Leger dress) attends the 2013 MTV Video Music Awards at the Barclays Center on August 25, 2013 in the Brooklyn borough of New York City. (Photo by Jamie McCarthy/Getty Images for MTV)
This was pretty on her. I believe she'd JUST started playing around a bit more with fashion? The hair isn't quite coming together, but she looks great in the dress -- which is another one I might have saved for, say, an Oscar party.
In 2014, in Mary Katrantzou
Los Angeles, CA - Taylor Swift arrives at the 2014 MTV Video Music Awards held at The Forum in Los Angeles, California. AKM-GSI August 24, 2014 To License These Photos, Please Contact : Steve Ginsburg
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And then HERE WE ARE: The leotard. This was so silly, and totally looks like a puzzle straight out of Dolce & Gabbana for The Da Vinci Code.
Los Angeles, CA - Taylor Swift arrives at the 2014 MTV Video Music Awards held at The Forum in Los Angeles, California. AKM-GSI August 24, 2014 To License These Photos, Please Contact : Steve Ginsburg
(310) 505-8447
(323) 423-9397
steve@akmgsi.com
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But I think it's the fit that was the worst, honestly. This manages to be a wedgie that's also still a bit baggy?
Los Angeles, CA - Taylor Swift arrives at the 2014 MTV Video Music Awards held at The Forum in Los Angeles, California. AKM-GSI August 24, 2014 To License These Photos, Please Contact : Steve Ginsburg
(310) 505-8447
(323) 423-9397
steve@akmgsi.com
sales@akmgsi.com or Maria Buda
(917) 242-1505
mbuda@akmgsi.com
ginsburgspalyinc@gmail.com
And this is gapping right at her crotch. TAYLOR. If you're going to do this, there is no room for error. Not a millimeter.
INGLEWOOD, CA - AUGUST 24: Recording artist Taylor Swift performs onstage during the 2014 MTV Video Music Awards at The Forum on August 24, 2014 in Inglewood, California. (Photo by Lester Cohen/WireImage)
On-stage, for "Shake It Off," she went very Ice Princess. It looks fine but I liked her skipping around in stripes better, although literally shakng while wearing fringe is probably fun.
in 2015 in Ashish
attends the 2015 MTV Video Music Awards at Microsoft Theater on August 30, 2015 in Los Angeles, California.
I can't go with her on this journey, though. Metallic houndstooth, sure. But that much midriff while also being a tracksuit? Pass. She's feeling her edge, but I'd rather avoid that cut.
2015 MTV Video Music Awards - Fixed Show
LOS ANGELES, CA - AUGUST 30: Recording artists Taylor Swift performs onstage during the 2015 MTV Video Music Awards at Microsoft Theater on August 30, 2015 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)
And, more of the Drum Majorette look, although I appreciate this picture for being an instruction manual on how to spray-paint abs on a dude.