A classmate once told me in high school, “You’re so different from what I imagined you’d be when I saw you in the hallway.” I asked what she meant. “I just thought you’d be stuck up.”
That hurt because I’m a dork. I am a goofball. I feel awkward. I feel like Bart Simpson in a woman’s body.
But the assumption that I must be cold, vain, or superficial is something I can’t seem to shake. Just last week, after a dinner party, a guy I barely spoke to told someone I seemed like a “normie” and stuck up. But then he added that he found me attractive. Later, the guy relaxed when someone who’d talked to me shared more about who I am. We ended up becoming friendly.
This kind of thing happens a lot in San Francisco. I like being feminine. I like wearing makeup and dresses. But among the Bay Area’s bohemian bourgeoisie, this is often seen as passé and unintellectual. It is beyond me how it never occurred to these people that associating femininity with vapidness is incredibly sexist.
It’s actually 4D chess class performance. Dressing down becomes a signal of moral or cultural superiority, and to signal that you are upper-middle class and not gauche like those trashy poors. Makeup and heels are for the working class, for women who have to perform femininity because their appearance is directly tied to feeding themselves.
“Ugly chic” is empowering because it shows you don’t have to try, as you’ve already made it. It’s the feminine version of tech guys in hoodies and dressing like slobs, LARPing humility as virtue. West Coast pretension sold as progressivism.
I’m working on being more positive, but I have to admit: being a woman who looks a certain way can be profoundly isolating. Yet I refuse to dress down because 1) if you are Black in San Francisco and wear a hoodie, you are automatically assumed to be homeless, and 2) it isn't honest.
This isn’t just about makeup. Objectively speaking, I’ve been told I’m attractive since childhood. I’m aware that beauty is subjective, and I don’t think I’m the most beautiful person in any room, but I’d be dishonest if I pretended my appearance hasn’t shaped my experiences. It comes with some privileges, yes. But it can also feel like a curse.
When I was 14, I got my first job at a Lebanese restaurant in suburban Detroit. One day, a Black girl who was maybe 19, with a bright smile and a warm presence, came in to apply. After she left, the owner looked at me and said, “Nobody wants a girl like that serving them. She's all loud and stuff. It’s not what anyone wants to see at a restaurant.” I understood even then that the small dose of “pretty” people saw in me could shield me from certain kinds of pain that no girls should ever have to endure. I say this to acknowledge how complex all of these things are.
But the so-called privilege of prettiness carries its own pressure: the incentive to disappear. To shrink.
People project their insecurities onto you when you’re “exceptional” in any visible way. And you’re left with two difficult choices:
Shrink yourself to make others comfortable. This rarely works, but it feels emotionally safer. Making yourself small is a strange relief when your presence seems to agitate people.
Be yourself and risk being misjudged or shut out. Refusing to minimize yourself means facing social penalties: distance, suspicion, gossip. In my experience, women are especially hostile to outgroup members(if you don’t believe me, tell me the next time you see a multi-ethnic friend group of women, even in multi-ethnic cities. It is rare.)
I’m trying to choose the second option. To be myself, unabashedly. But that’s complicated, too, because when people are comfortable with a woman being “pretty,” it’s usually under very narrow terms. You can be pretty, but then you must also be dumb, shallow, or mean. There’s rarely room to be both beautiful and interesting. Stylish and kind. Smart and goofy.
What’s most frustrating is that it gets dismissed when you try to talk about this, especially with other women. It’s taboo to speak about intrasexual conflict. Second-wave feminism taught us to treat such tensions as distractions from “the real issues.” But that erasure doesn’t make the problem disappear. It just silences the women who live it. Many people don’t have an issue, so it’s easy to brush off as arrogance or delusion.
I should note that, while women bear the brunt of these projections, men aren't exempt from the weirdness. Sometimes they objectify. Other times, they dismiss. Maybe, project all their hopes, dreams, and sunshine onto you.
Of course, it can sound ungrateful to complain about being seen as attractive. Kind of like if a billionaire complained about being lonely, you’d want to roll your eyes. But actually, I think there’s something to that. “Privilege” can be profoundly alienating. It separates you from specific communities, understanding, or real connection forms.
That doesn’t mean we equate beauty with oppression, or wealth with victimhood. It means we need better language for complexity.
"Bart Simpson in a woman's body" is the best visual, and I know exactly what you mean.
My friend and I talked about Shrinking before, but we described it as 'feeding the tigers'; you have to give them some offering of self-deprecation and keep their insecurities fed so they won't eat you alive.
Gods, I relate to the Shrinking so much. For me, it's never shown up in femininity presentation - I mean, somewhat obviously, since I only really could /engage/ with it in the last decade and all, what with trans-ness - but I've always had other places I was - well, exceptional is a good word for it, indeed.
And you learn to hide that, because people don't like it, and it sucks.
But I /also/ relate to 2), since when I -did- transition, that was kind of when I decided I was done shrinking. And yea, it means a lot of people get ruffled feathers by me, but I let that wash off my back. I want to find my people, and that means sometimes finding people who aren't my people. That's okay.
That said - I do get the party comment, cause if we weren't already friends I could see myself thinking the same until we get to talking - but I think that too is because you learn that dress style often correlates with personality. The language I am used to being expressed in that more upscale style reminds me of like, the middle-upper class culture I grew up in, that in some ways the tech dressing down I feel is a rebellion against.
Like, oh - I think of it like the difference between New York & SF. New York is the land of finance and suits, high pressure Serious People (or at least it presents itself that way), while SF is the land of the scruffy nonconformist who is rough around the edges, but well-meaning and clever. Steampunk to New York's more traditional kinda...Nasa aesthetic,or something :D
Back east? I'd agree, the dressing up is a 'You have to to be taken seriously' kind of thing, but out here I think that that same style sends a different cultural signal than it does where we grew up.
Does that make any sense? Hopefully!