“I dress like a boy because I feel like boys are generally more comfortable than women,” said Ali Tenenbaum the other day, sitting at a West Village coffee shop and wearing a “typical” outfit of black Hudson jeans, blue J. Crew cardigan, yellow T-shirt and designer sneakers. Ms. Tenenbaum, 38 (whose family was the inspiration for the Wes Anderson film The Royal Tenenbaums, though she said the actual resemblance is slight), has unfussy brown hair that falls to several inches above her shoulders, and clear, radiant skin. She doesn’t wear makeup. She is a professional photo organizer who meets with her (largely) Upper East Side clientele wearing sneakers. “Sometimes it throws them off a bit, but then I charm them and they’re fine with it!” she said.
It was just a few years ago that everyone was nattering about the metrosexual, the New York man who, though straight, loved his Kiehl’s and Thomas Pink tattersall shirts and is addicted to Grey’s Anatomy. Less discussed has been his female counterpart: gals who, while not lesbians, dress like guys (young guys), well into their 30’s; who leap into games of pickup basketball with male friends while the rest of us watch wanly from the sidelines; who affect a wry detachment from their sex’s conventional concerns of shoe-shopping, man-hunting and family. Think of the comedienne Sarah Silverman, mugging and shrugging and strumming her way through an “I’m F*cking Matt Damon” video, a birthday gift to her boyfriend, ABC talk-show host Jimmy Kimmel. Or matter-of-fact Juno actress Ellen Page. Or surly pop star Avril Lavigne.
And these gals are everywhere in New York. Urbane tomboys in $200 jeans, they wear sneakers to the office or the studio (they probably work in a creative industry). They’ve largely given up on mainstream women’s fashion, with its expensive, often unflattering vicissitudes, finding refuge in an eternal sporty girlhood that may or may not be tied to any real athletic bent. They borrow from men’s wear, which is more constant, comfortable and, lately, focused on well-made basics like jeans and T-shirts, and they profess ignorance of female grooming rituals, even if they have a secret love of eyeliner. Ever self-deprecating, this kind of woman is quick to tell you she “wears the same thing every day,” or that she dresses like her husband or boyfriend.
‘I Like to Keep It Basic’
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.
Ms. Silverman, particularly, whose status as a sex object is partly the product of the tension created by her potty mouth and her JAP-y good looks, dresses like she’s on her way to intramural softball. It’s a look that basically says, I’m too cool for dresses, a direct commentary on an ever-more-exhausting mainstream feminine aesthetic. The urbane tomboy cares without seeming to care. Because she’s hot enough to succeed without the embellishment, and she knows this.
Key to this type is a certain willful naïveté about the baffling stratagems of conventional female life.
“I do try to be more girly,” Ms. Tenenbaum said with a shrug. “I try to buy poufy sleeves, even just a cardigan with a poufy sleeve. And I put it on and I just can’t do it.”
They like to order Scotch at bars, rather than fruity drinks like cosmos; roll their own cigarettes; and profess to not know their way around a powder puff.
“I have my products. But I’m sure I don’t know what the hell I’m doing,” said Gillian Schwartz, 30, co-owner of a brand consulting firm, Parisi, whose high-profile fashion clients includes Vena Cava and Steven Alan. “When they start getting too specialized or tricky. … I guess I don’t like tricky. … Essentially, if you’re a pretty lady, you can just kind of let that …” She trailed off. “Well, I have no idea where I am on that, but I just like to keep it basic.”
Ms. Schwartz, a tall, bare-faced brunette, was drinking cappuccino in Nolita near her office the other day in a monochrome shirt and cardigan combo and slim brown corduroys. “I almost feel clownish when I get dressed up,” she said, echoing Ms. Tenenbaum. “There’s a real apprehension, especially in the creative industries, to not be overdressed. Overdressed is pretty bad. Underdressed is cool.”
To be an urbane tomboy is to have a certain condescension toward feminine adornment (even, or especially, when it’s the source of one’s livelihood). Or at least, a sense that in serious times, we should be thinking about other things. “Maybe people don’t feel as comfortable being all blinged out anymore,” suggested Ms. Schwartz. “There’s some bad stuff going on that we’re responsible for.”
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.”