How I Learned to Express (and Appreciate) Gender Identity Through Fashion

When I turned 31, it was time for a fashion upgrade. The pressure of starting my 30s had subsided, and I was now solidly, joyfully in this new decade of life. For a New York City apartment, I had an impressively large closet with three mirrored doors, the middle of which was broken and off the tracks. While I waited for a handyperson to fix it, I stared at my hanging clothes day and night, surprised at how many old versions of myself still existed. Versions of myself I no longer recognized.

Growing up multicultural, my dad from the Czech Republic and my mom from Puerto Rico, my parents were strict with certain rules, like dishes and yard work, but we had free range when it came to self-expression. My parents let me dress myself, since as far back as I can remember. I'd leave the house in mismatched tall socks and a backward hat, play with colors and patterns. Every day was a new chance for gender expression.

That changed when I switched from my beloved public school to a private school with a classic prep-school uniform of a plaid skirt, a white button-up, and a sweater vest. Popularity was now determined by who had on the newest Tiffany necklace, not who was the most down to earth, the way it had been at my old school.

I felt entirely out of place. I didn't understand why the Catholic teachers hovered above me as if I was always about to sin. On the days I wore nail polish, a teacher would remove it to embarrass me in front of other students. I once drew a heart on the back of my hand in class and got detention. "You won't be taken seriously as an adult if you have written all over you," my teacher said, hoping to nip in the bud any future tattoo fantasies. To them, self-expression was dissidence. And traditional male/female roles were not only expected but also enforced through uniform.

My friends and I would wear shorts under our skirts, giving ourselves a little more freedom of movement. While I can see the benefits of a uniform, primarily to get students to focus more on their studies than their outfit for the day, being confined to a skirt made me feel I couldn't be myself.

In Puerto Rico, I felt the same pressure to be more girly. I stood out from the moment I waited for my luggage at the turnstile of SJU airport in an oversize hoodie, beside women in full faces of makeup and platform heels. On the island, my tomboy style didn't translate. As if my baggy jeans meant I wasn't trying hard enough, rather than a purposeful choice.

Even in the privacy of my family's house, gender roles applied. One day, I painted my nails pale blue, and my little nephew begged me to paint his, too. He held out his pinkie finger, and I swiped it with thick polish. He held it in the air, excitedly waiting for it to dry.

"Just don't let his dad see it," my aunt warned. This was code for "we can have as much fun as we want, but when the men arrive, their masculinity will be threatened."

A fun moment between my nephew and me had been brought down to earth. Back where we hold so tightly to our gender norms that a little boy now believed he'd done something wrong by having a little fun with nail polish. Repressing the part of himself that was free to explore. We, adults, tell kids how to dress and how to be, when in reality, they know good and well who they are and what they want. If only we'd let them.

Because of my years in prep school and my summers in Puerto Rico, I never considered myself a feminine girl until my femininity was taken away. When I was 19, I was diagnosed with cancer and went into full-time chemotherapy.

My hair and eyelashes fell out, and I felt less of a woman. My curves diminished, my softness turned to the bone as I lost weight, and I felt less of a woman. The rosiness in my cheeks went white, my cheekbones hidden by puffiness, and I felt less of a woman. On my last day of radiation, the technician told me I was beautiful, and I was sure he was patronizing me because I was not by any metric I had ever been taught growing up.

As I stumbled through recovery, I wanted nothing more than to feel like a woman again. I entered the modeling industry in New York City, envisioning couture gowns and glitzy-styled outfits. But on my first day on the job, I learned models have uniforms, too. Our agent lined us up for weekly meetings to inspect our outfits that consisted of skinny black jeans, a tight tank top, and black stilettos. For every one fabulous job were 20 to 30 castings in uniform. My drawers at the time resembled that of a cartoon character, multiples of the exact same look, one for every day of the week.

Now, without any uniform, I play with both extremes of my gender expression. A pink tulle dress or black cargo pants, your guess is as good as mine.

But no matter which I choose, I know what type of day is ahead based on how quickly I get ready. If I grab an outfit off of a hanger, throw it on, and head out the door without a second thought, I know I'm aligned and in flow. If I try on 10 tops, making a mess of my bedroom, I know I'm feeling insecure and trying to adjust myself to please others.

I stared at my open closet, packed with clothes, like a time capsule from my other lives. I saw the sweats I wore to the hospital for chemo, I saw the hoodies I wore over my prep-school uniform to try to stand out, I saw the skintight black denim I wore as a model.

I've been dressing to please other people my whole life, but now at 31, I'm finally ready to dress for myself.