The Urbane Tomboys

It’s a condescension that’s returned, of course. One unapologetic fashion enthusiast, a handbag designer who asked not to be named, recalled seeing a young UT recently at the Belmont Lounge in Union Square: “She had on sweatpants, what looked like a vintagey-type T-shirt, a men’s American Apparel-type hoodie, which was huge on her model body, and then one of those big floppy painterly homeless-person hats. And Josh Hartnett was hitting on her. And incidentally, he was dressed the exact same way.”

Pedaling in Prada

It’s not that urbane tomboys are philosophically opposed to shopping, exactly.

“It’s only been in the last two years that I’ve admitted I like to shop,” said Ms. Schwartz. “I thought it was so frivolous. I was kind of embarrassed by it.”

Ms. Tenenbaum admitted she trawls “Old Navy, Barneys, Jeffrey and everywhere in between.” But they both say they’re looking for comfort and quality, not for trends, and that they’re interested in blending, not standing out (at least not for something so insignificant as clothes). For that reason, they’ll wear a dress when absolutely necessary. “I will wear a dress to a black-tie event. I won’t wear, like, a man’s tuxedo,” said Ms. Tenenbaum.

“If I’m going to a house party, I’ll wear a dress, all right?” Ms. Schwartz said. “Of course, I’ll dress it down with the shoes or a giant blanket or something. I just don’t feel comfortable being, like, Charlie’s Angels style.”

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.”

A direct descendant of the Audrey Hepburn gamine and the bra-eschewing hippie chick, the urbane tomboy’s fashion rebellion is absent political message, or anger: it’s more of a casual shrug toward the strictures of femininity.

“I read women’s magazines for a living, and they’re always trying to convince me that ‘now you want your wide-legged jeans!’” said Moe Tkacik, 29, who writes for the women’s-issues blog Jezebel. “And now they should be high-waisted! And it’s like, motherfucker, if even 3 percent of your readers buy high-waisted, wide-legged jeans in response to this proclamation, womankind has lost. Because they look bad on everyone.”

Ms. Tkacik’s job does not require that she leave her apartment on most days. Consequently, she said, “I basically dress solely in black jeans and canvas shoes of some sort.” She motioned to her black Edun jeans. (“They fit, they’re fair-trade,” she deadpanned. “Kidding!”)

“The quicker you come to New York, the faster you’re just like, ‘Fuck this,’” Ms. Tkacik said of fashion norms. “There are other exploits where I am more likely to succeed.” (She is currently writing a book on “the economy and its addiction to ‘demand creation.’”)

But this particular style is not about giving up, sartorially speaking; it’s a conscious direction of the messages one’s clothing is sending. “I am a ham at times,” said Kristin Flammio, a comely 26-year-old who works as an assistant to the head of men’s design at J. Crew and doesn’t wear makeup to work. “I also am a musician, so part of me always wants to be the center of attention, but I feel like I don’t need to dress like I want to be the center of attention.”

Ms. Flammio admitted that she and her boyfriend dress similarly. “Men’s design doesn’t really vary too much, and I appreciate that,” she said.

Many fellas, as girly girls can attest, are all too enchanted with the novelty of the urbane tomboy.

“If you go to a club and you pick someone up and they’re all dressed up and they have a lot of makeup on, you take them home and you roll around in bed and they wake up and take a shower, who knows what they’ll look like?” said Adam Parker Smith, 29, a sculptor from Brooklyn.

“Reducing that element of gamble or risk and sort of knowing what you’re getting is appealing,” Mr. Parker Smith continued. “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.” (Incidentally, Mr. Parker Smith is currently seeing a woman who dresses similarly to him, except that “her jeans are much tighter,” he said).

Not everyone, however, sees the appeal.

“Guys think Sarah Silverman is hot, generally speaking, for a funny girl,” said Gabe Gigliotti, 29, a painter and illustrator who divides his time between the coasts. “I guess I find her attractive,” he said, adding that he often sees her out and about in L.A. dressed like a “teenaged boy.”

“I know guys who love that, who love girls who are like one of the guys,” Mr. Gigliotti said. “I never was that into that, because I don’t think that the guys in general are that cool. To be a girl who also gets high and sits around drinking and watching sports … It’s not exactly a turn-on. I don’t really like myself, so for a girl to be like me just isn’t something I want.”