Rainbow socks and beat-up Converse are all the rage at Portland Pride Parade. Photo by Katrina Cole.

I’ve noticed over my teaching career that kids possess a keen insight into the phenomenon of privilege. Curious about privileges I might take for granted, I asked four trans* teens I work with, ages 15-20, five questions about fashion. What I learned is that what we wear has a lot to say, not only about who we are, but about who we are expected to be. The way these kids express themselves through fashion challenges our culture’s common assumptions about gender identity. I should also mention that these kids are frustrated by those assumptions, which is why they asked me to identify them by just letters: W, X, Y and Z.

What do you wear to feel more like yourself?

W: T-shirts, jeans, typically more of a baggy cut, though. It’s more safe. I can’t wear tight clothing anymore without being outed because even with a chest binder, you’re not getting very much flattened out. I still like dark, heavy eyeliner, but there’s this part of me that’s afraid to wear cosmetics now.

X: I’ve dressed as male since I was about ten. That’s when I cut my hair. Right now, I’m wearing guy’s pants, my brother’s sweater, a button up and a tie. I have both ears pierced. Nowadays that’s not a very genderized thing.

Y: Most of the time I just wear things that are considered more unisex so I’m able to feel more neutral, which is the way I identify. I try to wear bigger t-shirts or flannels or vests. But there are days when I want to wear a skirt and feel adorable. I don’t wear a ton of makeup, mostly because I don’t know how.

Z: For my first pair of shoes, I wanted the pink, glittery, feathery shoes. I like colors. Stilettos. I have a pretty elaborate collection of high heels. It’s almost like an art project for me. I recently pierced my ears. That was a big deal for me. I taught myself makeup. I wear breast forms. I always wanted boobs, I guess. I picked a size that was somewhere in the middle. I’ve grown my hair out ever since I came out.

What was it like for you before you had the ability to make these choices?

W: I was, I guess you could say, blessed with my mother. She let me do my own thing. My father pushed me to be more feminine. He didn’t want me to be a lesbian. Shocker! I was not born a woman, I was born a boy in a girl’s body.

X: I felt very odd when my aunt tried to paint my nails. I’ve always seen it like, “Why aren’t you treating me like my brothers?” We grew up as boys together.

Y: I was always kind of a tomboy in elementary school. Out in public, I would get called a boy. Everyone knew me as a pretty masculine person. So by the time I was in eighth grade, I felt like I couldn’t wear dresses, like it would be weird if I looked like a girl.

Z: I came out in 6th grade, when the guys were supposed to chase the girls and the girls were supposed to run away. I always wanted to be chased. That’s when puberty started to kick in and I realized something was wrong.

What keeps you from wearing what makes you feel comfortable?

W: Because I’m just barely 5’ tall and 94 pounds people are always going to assume that I’m female. I have to wear preteen boy’s clothing, which limits me to childish choices. Anything that looks classy or dignified in my size is tailored for females. Female dress shirts will emphasize the bust and the skinny waist. That’s not something I want to emphasize. A lot of my problems could be eliminated if I could afford hormone treatments. If you have facial hair, then people will think you’re just a short guy.

X: Early on my family had a hard time, you know, seeing the change. Of course, they were expecting me to be this princess. So I felt more comfortable at school than at home. I was always ready to go to school. That was before I had a chance to talk to my mom about it. My mom has my back now.

Y: Mostly self. I had all this awful internalized misogyny. It’s hard for me to embrace the feminine because for so long I suffered from the idea that something super feminine is bad: girls who wear makeup are dumb or girls who wear skirts all the time are weak. All this awful stuff. This school has allowed me to explore who I want to be and to embrace my feminine side.

Z: I don’t feel comfortable out of school. Some creep said something really nasty and gross and followed me off the public bus. All I could do was say, “Back off!” in a very powerful man voice.

What does all this say about gender roles in our culture?

W: Uh! They’re such bullshit. You’re trying to put millions, billions of different types of people into two categories, men and women, and it doesn’t work. We judge people based so much on how they look, you feel unsafe leaving the house wearing something that doesn’t match your gender role. There needs to be a massive paradigm shift away from binary.

X: I think it’s changing, a more even playing field.

Y: I thought the only way I was going to be perceived as really strong was if I looked more masculine. Anything feminine was weak or unintelligent. Fashion is so closely tied to your worth. People think a woman wearing a blazer is going places, but if she wears a low cut top she’s not.

Z: When that creep followed me, I shouldn’t have had to make my voice deep to be respected.

If you could change one thing about fashion in America, what would it be?

W: Media makes it difficult to function outside the norm as far as fashion goes. Media could put an emphasis on neutral clothing instead of having to objectify women constantly and making it hell to try and find a good dress shirt that doesn’t make your chest puff out like a damn peacock.

X: I’m not sure that I would change anything. The more binary fashion is, the easier it is for me to pass. The general public would say this person is wearing this so they are male. Just as an observation, though, in a rigid gender binary there isn’t that fashion middle ground for a person who is more fluid in their gender identity.

Y: People are okay with a girl superhero at Halloween, but when a boy wants the princess costume, people aren’t okay with that. So I would change the idea that masculine is the only good thing and that anything feminine is lesser.

Z: I’d like people to be more accepting of men wearing feminine clothes and women wearing masculine clothes. I’d like to be somewhere in the middle, more feminine but still be accepting of the body I have. I’d like to live in that duality. I can’t do that at the moment.

Related Reading: When I Say My Daughter is Transgender, Believe Me.

Benjamin Dancer has made a career out of mentoring young people as they come of age. He wrote the novel Patriarch Run, and he also writes about education and parenting. Learn more at BenjaminDancer.com.