Taylor Swift. Teenager, country music. She always wear dresses. But what do the dresses mean?
I’m impaired talking about women’s dresses, impaired because I’m a guy and impaired because I developed a habit early on in my traumatic adolescence of not comprehending what I was seeing, of turning off the brain inside my eyes: The way I dealt with fashion was not to think about it.
So, last Friday night I was in a coffeehouse, sitting across from my gorgeous friend Keenan, who’s never heard Taylor, but I nonetheless wanted her to explain Taylor to me. I’m trying to describe Taylor’s dresses, that they don’t simply go down to a hem, they flow down, some of them with vertical folds … is the word “pleats”? … sometimes one part of the dress going down to here and another part in back going down farther. There must be a word that describes this look, a term that everyone knows but that I don’t.

[…]

Why does Taylor Swift always wear dresses? Pink ones, or light blues, she’ll wear them, not necessarily “elegant” dresses, but not homey or homely or plebian or workaday, either, but bright with a sexy flow. Keenan, comprehending what I could not, hearing my description, says, “They’re summer dresses!”

[…]

[S]he’s helping me to understand summer dresses. “Summertime dresses … You can whip ’em off in a second, go in a creek, or even go into the creek with the dress on. Wearing a dress like that is like wearing a cloud.”

So in effect she’s telling me that Taylor’s summer dresses can be freedom dresses.

Frank Kogan, “The Rules of the Game No. 28: Dresses are my weakness, seriously," Las Vegas Weekly, January 24, 2008

Sady Doyle:

I have no idea why anyone would interpret a woman in her twenties who affects a cartoonishly shy demeanor and wanders around all wobbly and doe-eyed in frilly white baby-doll dresses […] as somehow pandering to our larger cultural desire for infantilized, soft, non-threatening, non-aggressive, defined-by-their-relationships, I-fuck-to-get-closer-to-my-boyfriend-not-for-the-love-of-fucking little child-women.