It wasn’t until 2016, when I was 35 years old and had been on testosterone for a year, that I started to wear makeup. There had been a brief period in my teens when I tried and failed to become a make-up wearer, streaking too-heavy foundation across my skin, wearing neutral lipstick and lip gloss. I hated it, then. I hated the idea that I was creating a version of myself that was just like myself but a little less flawed with makeup. It seemed like a waste of time, money, and effort to do such a thing. What did I care if my skin wasn’t perfect? The eyedrops I used to moisten my contacts (then less disposable than the ones I wear today, and meant to be worn for a whole year) meant I couldn’t wear eyeliner or shadow. What was the point?

That is what I told myself, anyway. I didn’t wear makeup from the time I was a teenager until I was 35. Around age 29, I had another realization as to why, and that was that I wasn’t a woman. It came as a shock to me to learn that I had been in the closet as a trans person for most of my life.

Some transmasculine people, when they first transition, go deep into toxic masculinity. Surrounded mostly by trans women whose femininity was some of the most gentle and caring I’d ever seen, I knew this would not be my path. I went back and forth for about five years about whether or not I would medically transition. When I finally started taking testosterone, something inside me changed. I was no longer “proving” masculinity from a body that could never be read as anything but feminine by most. As my body hair grew thicker, and I began to be able to grow a goatee, I suddenly embraced makeup, too.

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My first lipsticks were eyeliners: pink, purple, and blue. I picked them up in a CVS in the small Ohio town I’d moved to after my divorce because they didn’t have anything but reds, mauves, and taupes in the lipstick section. I put the blue one on the day of my best friend’s graduation from college and asked how it looked only to have her grandmother reply, “You look cold.” (My best friend and I still laugh about this.)

Experimentation is part of wearing makeup that I never really went through as a young woman. Now, as a transmasculine nonbinary person, I felt less afraid to make mistakes. I felt more entitled to wear makeup than I had as a young woman. And I felt that if I was going to do it, I was going to do it boldly.

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I toyed around with makeup for two years before I found a brand on Instagram that was everything I wanted – bold, long-lasting colors, metallic powders, sparkles. All of it was perfect for my taste and affordable. The brand was Tattoo Junkie, and while I still don’t know enough about makeup to know whether that’s an embarrassing line to admit having as your favorite, it’s true. I started with some purple and green lipsticks that came with glitter toppers.

I felt perfect in them. I felt exactly like I wanted to look. At the end of 2019, I was wearing them out to events, and to school, and to parties. Strengthened by what felt like success, I dove into the line and began to buy more.

I bought a bronze metallic powder that I began to put in the corners of my eyes, along the line of my brow. When I went out in Cleveland, douchebag bros would look at me and laugh, but I couldn’t have cared less. It wasn’t like I was trying to fit in with a banker crowd walking around with a goatee and unnatural colors on my lips and eyes. 

In 2020, when the pandemic hit, I started in with glitter. I bought green and silver and gold, I wore it over my eyelids. I found a gold shimmer lip gloss online. I found tubes of iridescent sparkles in many colors in a Walgreens and began to spread them across my eyelids, in the hollows of my orbital sockets, just under my brows. Often, the long dreary days of the shutdown could be made better by something extravagant over my lips and eyes as I walked to the corner store to buy cigarettes. When I did Zoom readings, I went all-out, channeling David Bowie in the ‘70s. 

It seemed to me, suddenly, that I had become the person I had always wanted to be. I was someone who could wear what I wanted, despite and maybe because of notions of gender. I was a person who was creating a flamingo masculinity for myself, a kind of masculinity I not only embraced but further fostered with clothes I never would’ve worn before, shoes I could barely afford and searched for deals on Ebay. I was walking into the world with a confidence I’d never had before, either. I was no rock star, but I carried myself just like one, and when bros weren’t making fun of me, people were starting conversations with me, attracted to me in ways they never had been. I bleached my hair blonde. I posted selfies. I cared how I looked, now that I had become this sparkling, between-gender, not-giving-a-fuck presence in the world. 

Makeup doesn’t change who you are, entirely. But allowing myself to embrace it as costume and joyful expression has entirely changed my presentation in the world. I walk around in sequined vests and shirts, wearing Fluevog rock star boots, acting like I’m someone worth knowing and speaking to – something I’ve had hard time believing for most of my life. While the real, internal change towards believing those things came from hard work on myself and to dispel a negative self-image I’ve carried before and into my gender transition, one of the first steps towards doing so was embracing that which made me happy to look in the mirror. 

Alex DiFrancesco is the author of Psychopomps, All City, and Transmutation. They are an Assistant Editor with Sundress Publications and a Literary Arts Director with Sundress Academy for the Arts. They live in Cleveland, Ohio, with their Westie, Roxy Music, Dog of Doom.