The Urbane Tomboys
Eschewing makeup, enjoying a game of pickup basketball, and maybe eyeing your boyfriend! It’s the New York woman’s answer to the metrosexual

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The Observatory
“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.” Next Page >




















Sarah Silverman and 'good looks' should never be used in the same sentence.
Imagine the time she spends to give herself some semblance of a non-hairy look.
What you may not know is that Ms. Tenenbaum in one of the most attractive and adorable human beings in the world. She is genuine and smart--she looks like who she is--the best of all.
Where's the photo gallery? Let's see some hot UT pics!
Having grown up as a tomboy, I can tell you that pretty much everything in your article is wrong. By and large, a tomboy doesn't eschew wearing make up because she already knows she's hot. A tomboy doesn't wear make up because it's feminine and she isn't, or doesn't feel feminine and wouldn't know what to do with herself if she did. Dresses, frills and the like make her uncomfortable. She is genetically female but is almost completely out of touch with the way society deems a woman should act like. She doesn't do it because it's cool.
I'm not going to judge the women in your piece as whether they are or not actually tomboys. But Ms. Bryan, there's a shocking lack of understanding in your article as to what a real tomboy is.
I am shocked that you used the word "shocking" during your reprimand.
I have to say, I resent the "tomboy" moniker. Women who don't wear skirts and dresses and make-up must want to be men. Wrong. I am a jeans and t-shirt girl, sneakers to work under my business casual pants and plain shirt, no make-up, etc. I wouldn't want to be a man for anything. I don't enjoy watching sports on tv or playing them for that matter. I just don't feel the need to waste my time and energy making myself attractive to men every single damn day.
The dichotomy that's implicitly set up is that a woman's primary motivation is either to attract a man or to be a man. There is definitely some space in between where I think most of us so-called "UT's" reside.
Am I the only one who thinks its incongruous that the accompanying photo is of a young woman (one featured in the article) wearing makeup?
I think it's pretty funny that The Observer came up with a name for this "lifestyle." Literally, everyone in California dresses this way. And has for decades.
This is a trend, or new or something? I mean, I've been making an ass of myself trying to impress women like this since the mid '80s. Some self-aware, confident women opt for comfort over costumes and they pull it off with a who-gives-a-shit sexiness? What a revelation!
I'm pretty sure this article was written in 1950. Meredith Bryan should next check out this new rock 'n roll music I'm hearing so much about.
WHY is this news? Did you run out of interesting things to write about? Who give a sh*t if some women like to wear jeans and sneakers and others like to wear heels all day everyday. That doesn't make the women who don't tomboys and it doesn't make the women who do hookers. Stop making gross over-generalizations and start doing research on the stuff that people actually give a sh*t about.
Oh my... this article is so obnoxious it hurts.
This story is a joke right?
Not only is it poorly written, but it managed to combine New York elitism, serious analysis of utter bullshit, and self-absorbed women all into one article. Well done!
Why is there such a need to label everything? Some women like makeup and others don't. But let's label it and call it a trend. That'll make the masses feel better. Create a category and box it all in, all nice and neat so we can study it and point "Oh my no! That's not me! I'm BETTER THAN THAT!!"
Be true to yourself. Lipstick and heels or chapstick and sneakers. Stick the labels on the cans in the cupboard and leave my bare face alone.
MAKEUP OR NO MAKEUP WE ARE STILL GOING TO FUCK YOU
Holy crap. You people need to seriously settle down. The point of the article is that IT'S NOT THAT SERIOUS so chill.
I think this article is awesome. I have to go to my little sister for make-up tips and have my mother telling me I need new clothes. That doesn't mean I'm a tomboy because, no nicole, I do not like sports either. But if your idea of fashion is so laissez faire then why do really care what she labels you? It also doesn't mean that I don't want to be attractive and cute every once in awhile. I just have a different approach. No its not a trend. THAT'S the POINT! We are too busy with other more interesting things to deal with it.
I'm afraid a few commenters who claim to be tomboys themselves have misunderstood the central point of this article and how "urban tomboy" is defined. First of all, the term "urban tomboy" is a term separate and greatly different from the traditional meaning of tomboy. These urbane tomboys are not your rough girls who play in the dirt and burp and spit and have no care at all for fashion. Urbane tomboys are the opposite. They, like the article mentions, wear $200 jeans, have a deep interest in menswear fashion, and know everything about grooming themselves. They are extremely familiar with makeup, skincare, and hair products, but they try to effect a look that seems as if it were entirely effortless. The ONLY difference between a girly-girl and an urban tomboy is in the final product, NOT the amount of preparation or effort that went into it. It's all about the look.
I love how far female freedom of expression has come when women can commit blatant acts of sterotyping like this article on and pass it off as some form of legitimate journalism.
But it's not objectification or even oppression of self-expression when women do it to other women right? That's the way you defend this diatribe to yourself, isn't it?
Just let people dress how they sodding want to.
The idea that women who don't necessarily wear make up and heels all the time somehow need a label is indeed frustrating. It seems that men can exist on any point in the spectrum, whereas women are relegated to being either girly-girls or tomboys (urbane or otherwise). The fact that an article like this even exists really says a lot ... it puts the whole idea that we're in a post-feminist era to rest, or at least calls it into question. So frustrating.
I can't believe everyone is jumping on this girl. I think it's a fun article, and true. There are lots of women, myself included, who would rather wear a hip long sleeve T and a cool pair of designer jeans out for drinks than a dress or some frilly top. I've tried, I can't. And yeah, I play pickup basketball, watch sports, wear makeup, and do my hair....somewhat..and I've been told I look hot while doing it all. My guy friends have told me to wear skirts more, or show more skin, but I don't feel comfortable, and frankly, I do just fine with men the way I am. Thanks for letting me know I'm not alone!
I like my $200 jeans, because my butt looks so cute in them. But to touch it is going to cost you $2500 for the first hour, $1000 for every hour afterward.
I agree, Gina. I definitely subscribe the feminist line of thinking but I do not think that this article does anything for or against women. It's just a comment. A nod to those of us who are not always on the cover of cosmo in our glitter and skin. And if we MANAGE to live successful and productive lives in the absense of heels and 500 shades of eye shadow we are still women, urban or not, tomboys or not. We get the job done and the men we want just fine. If you are comfortable in doing these things in Coach, pink sweater sets, and diamonds, great. If not, great.
Can i get group hug?
I relate to the women in the article. I've never been the girl to overprimp myself - either it was too tedious or it made me uncomfortable. For my senior prom I went to a salon to get my hair and makeup done, and in the end I washed it all off because I felt so queasy looking so UNLIKE myself.
While I don't take the article silly, I'm not that impressed by it either. As another commenter pointed out, women in other parts of the country are just as laid-back as these women. New York is a fashion capital, with a thriving street culture, so one's clothing here does take on more meaning than elsewhere. I wouldn't take it as a trend, though, that some women eschew the ultra-feminine gear. So what? I like to dress down because it's practical for what I do on a day-to-day basis, but if I was a young starlet with an unlimited clothing budget - who knows what I'd look like then?
Though I've been called a tomboy, and I've even admitted to feeling like a little boy in a grown woman's body, I envy girly girls sometimes. I'd like to be able to wear high fashion effortlessly - I don't do it because I know my discomfort would make me stick out like a sore thumb. And above anything, I value TASTE and SENSIBILITY. Maybe that's what the UT is all about.
I think the media is just taking more notice of how women and men dress, because there are almost no taboos these days, and any semblance of a pattern or trend is apparently newsworthy.
If this passes as a serious article about women's psychology and consumer behavior, all I can say is thank god I don't live in New York.
Ha ha. I love you, martial. And I like to wear pants when I'm tired, and heels when I clean my room. I must be an...urbane metro-tomboy?
This is not news. It is not a trend. Some of us just dress like this. How inane can you get?
I am curious as to the age of the author of this article. Because, due to her surprise at this seemingly growing phenomena, I am imagining a woman much older than the women she is writing about. She sounds like someone who growing up, attended schools whose dress code insisted that girls wear skirts.
This trend towards dressing comfortably and androgynously does not make these girls "Tomboys." Nor do I see it as a new trend. Sneakers, jeans, t-shirts and hoodies are iconic elements of American fashion for both men and women. Corporations like the GAP, and more recently (and more relevantly) American Apparel have made their fortunes based on this fact. In any rural area or college town in the US you will see girls dressed this way. In fact, it wasn't until I started spending time in New York, that I would see women hoofing it in high heels. Who in their right mind goes walking for blocks in heels? Take a cab already, geez.
I don't get the sense that the women interviewed are confused about their gender or uncomfortable with being women. In fact, I'd say what is confusing is this cultural idea that gender is something not inherent to a person, but rather, inherent to what they are wearing. It's not like these broads are taping their breasts down and "packing" for Christ's sake. I imagine they're wearing women's jeans, t's, shoes, and hoodies. Let us not forget the one gender fits all classics of course: Converse all-stars and Levi's 501s.
A guy friend of mine went on a date with a girl he was really excited about the other night. Afterwards, I asked him how it went. "Fine, but she's not as cute as I remembered." I asked him what he meant, he said "She was wearing make-up, like a lot of it, oh and these pointy toed heels. It just turned me off. We couldn't go on a walk because of her shoes, and I felt like I was looking at her face through a mask." Huh. I can't imagine my friend is the only guy who feels this way.
Don't get me wrong, I have an extensive collection of glamorous vintage dresses, and I've been known to do amazing things with eyeshadow and lipstick. But recently I've had to come to terms with the fact that if caught without my make up, or in a pair of pants, I suddenly feel less womanly, or less attractive.This is because from the onset of adolescence girls are given props for womanhood: deodorant, make-up, perfume, heels, hair dye, etc. As long as I've been "a woman" (age of 12) these tools have been in my arsenal. So of course it felt weird at first to go without these props. So as a challenge to myself, I've stopped wearing makeup on a daily basis, saved the fancy shoes for special (sitting down) occassions and started rocking corduroys and sneakers more often. I still seem to draw just as much attention to myself from the opposite sex as I did before. Only now I am dealing with far less douche-y jock types. Huh.
As a closing thought, I would like to add that given how hopelessly out of touch and frankly, square Ms. Bryan's tone is, I take offense to her describing Silverman as having "JAP-y good looks." It's cool if Silverman describes herself that way, or even if I do. But coming from Bryan she sounds, neither cavalier nor urbane, but rather like a vaguely anti-semitic Republican wifey speaking amongst her gal-pals at the country club.I don't care if Bryan herself is a Jew, self-loathing Jews are as common as self-loathing women, the latter of whom, I will say refreshingly, don't seem to pop up in this article.
I'd say men can only usually exist as male stereotypes.
That comment was in reply to Nicole G by the way.
Actually, I meant to include Democrats in the statement "but rather like a vaguely anti-semitic Republican OR DEMOCRAT wifey speaking amongst her gal-pals at the country club."
Most anti-Semites originate within the Democratic party going back to the KKK and other nativist groups at the turn of the century. Republicans are the biggest supporters of Israel.