"It's Like Looking Hot With a Handicap"

The New York Observer has an article about "Urbane Tomboys" which is apparently what they are calling this new (because women have never worn pants before) look where beautiful, wealthy women dress like dudes. The article, of course, defines dressing like a woman to mean high heels, makeup, and flashy accesories. Dressing like a dude, on the other hand, means sweatpants and hoodies. And no makeup (duh). (This is not very sophisticated thinking is it? "Me girl in pink, you boy in blue" as Tarzan would say. Or actually, I guess Jane would have to say that. I don't remember Tarzan ever dabbling in drag, thought that is one show I would pay good money to see). The article takes pains to emphasize that it's not about not being able to afford feminine clothes, but about choosing not to buy them. Or in other words, these are wealthy women wearing expensive clothes. Just expensive men's clothes. Or, expensive women's clothes that look like inexpensive men's clothes.

Jen Cawley, a 40-something architect with a 13-year-old daughter who lives on the Upper West Side, has a typically urbane tomboy’s relationship to clothing: It can be expensive and designer, sure, so long as it’s utilitarian. “I wear an orange reflector vest when I’m biking, and a helmet,” she said, explaining that she bikes most days to work. “I always wear pants. I had these unbelievably great Prada pants that just wouldn’t wear out! Prada has this fantastic material. I could bike in them endlessly. I’d get soaked in them, they’d dry.”

Now, of course there is nothing wrong with wanting to be comfortable or enjoying quality material (or going for muddy bike rides in Prada). Dressing casually or "down" is something women have been doing forever. But the catch is that often, the more privilege a woman has, the more freedom she has to do so. Which brings me to what makes me so uncomfortable about the article. When Adam Parker Smith, a sculptor from Brooklyn (why the random artist from Brooklyn? I don't know. To prove how underground and legitimate this article about this new trend sweeping the affluent members of New York society truly is? Probably.), is asked his opinion on these women who dress like men, he says:

“Walk down in Soho and I can guarantee that I’ll be attracted to hundreds of women, because they’re all dressed up and wearing high heels. Don’t get me wrong, that stuff is hot. But women who can look good in sweatshirts and jeans are also remarkable. It’s like looking hot with a handicap.”

The point being that you can dress like a dude as long as you are good looking and, in fact, doing so proves just how attractive you truly are. Wait? What happened to comfort? Apparently that is a luxury granted only those who can look hot while feeling comfortable. Meaning, if you are ugly or fat or displaying any other social deviation like not being white or wealthy or straight then you better keep getting up an hour early every morning to put on your makeup and pumps. But you should also feel silly while you do it.

In between glamorous appearances at awards shows, Ms. Silverman and Ms. Page—as well as more mainstream examples like Jessica Biel, Drew Barrymore and Cameron Diaz—seem to revel in sneakered, hoodied androgyny, thereby recasting femininity as something you can take off and put on again: an optional, mildly silly act that certainly seems to excite everyone but that one needn’t always make time for.

Calling "feminity" "an optional, mildly silly act" is problematic for two reasons. First of all, not every woman gets to decide when she is going to present a feminine appearance or a more androgynous one. Many are expected to always be feminine by family and their social setting and plenty more still have enough trouble fitting the socially accepted definition of "feminine" without throwing on a pair of baggy jeans, Prada or not. Second of all, equating an androgynous appearance with being more serious or less superficial only serves to reinforce stereotypes that to be feminine is to somehow be less serious or more superficial. And this is troublesome for even those women who are able to afford to buy, and look amazing in their Prada sweatpants. Because they are still women. And as Ariel Levy writes in her book Female Chauvinist Pigs:

Women who've wanted to be perceived as powerful have long found it more efficient to identify with men than to try and elevate the entire female sex to their level.

But

Even if you are a woman who acheives the ultimate and becomes like a man, you will still always be like a woman. And as long as womanhood is thought of as something to escape from, something less than manhood, you will be thought less of, too.

I'm not saying we all have to wear dresses in order to prove that nail polish and lipstick can go with smarts and a serious work ethic. We already learned that lesson from Reese Witherspoon in Legally Blond. I just wanted to point out that there is no get out-of-the-gender-trap-free card. Whether you dress like a lady lunching in pearls or a sk8ter boi in Marc Jacobs boxers, you will still have to struggle, along with the rest of us, in a society that refuses to acknowledge the whole colorful spectrum of gender behaviors and appearances.