"Makeup Makes Me Think of Freedom"—6 Trans Women On Their Beauty Routines

For trans women, the bedazzling, bedevilling world of cosmetics can be particularly fraught. Here, six Canadian women share their thoughts, routines and favourite products

For many women around the world, learning to do makeup—or rejecting makeup as a tool of the patriarchy—is a rite of passage. For trans women, however, the bedazzling, bedeviling world of cosmetics is even more fraught.

In mainstream media, trans women are often represented as creatures of artifice who rely on makeup to create false identities, or to deceive men into sleeping with us. But the truth is that trans women, like cisgender women, have a wide range of relationships with makeup and we aren’t trying to trick anyone. (You can’t pretend to be woman when you are a woman!) Makeup does, however, come with certain complications—when you’re trans, everything in life is just a little more extreme.

As individuals who are often forced to come into our femininity late or who do so in secret (or both), trans women face unique challenges in developing our aesthetic skills, self-expression and artistry. And when we are first breaking through the taboo of presenting in a feminine way, makeup can make us look more “obviously” trans, exposing us to transphobic violence. But as our transitions progress, it can allow us to blend or fit in more smoothly with stereotypical norms of feminine beauty. Depending on the looks we go for, makeup becomes a way to affirm, enhance, or downplay our gender identities.

So what’s a trans girl who’s just getting ready to take M.A.C or Sephora by storm supposed to do? I spoke to six trans women from across Canada about their thoughts, feelings and experiences with makeup, and this is what they said.

“Makeup made me feel more sure of myself when I really wasn’t”

A trans woman shown from the shoulders up. She's wearing a sheer black top with embroidered flowers over a black tank top.

“When I think about makeup, I think about ritual—makeup connects me with the Indigenous femininity of my cultural lineage. It’s something I have learned to cultivate over the years, a daily regimen that I perform every day before I leave the house. First, I wash and prime my face, then cover any spots with concealer. Next, I put on foundation and prime my eyes, followed by eyeshadow, liner and mascara in my signature cat eye look. Lately, I’ve been using NYX liquid eyeliner in bright, bright bright colours to create dots or shapes around my eyes.

Makeup made me feel more sure of myself when I really wasn’t, because it allowed me to navigate the world as a woman. It helped me navigate the world more easily, especially in a place like Halifax that has very low trans visibility.

Today, makeup is still something that I love doing. It’s fun to create different looks, and it’s interesting as someone who paints occasionally. I hide things in my makeup that people won’t see unless they look closely at my face. I’ve started adding Indigenous beadwork details to my makeup, like triangles with yellow or pink and turquoise. I feel that we need to remember that our bodies and the way we do our makeup, the way we hold ourselves in the world, is an act of art” —Arielle Twist, 23, Halifax

“When I do makeup, it’s because I want people to know that I’m trans”

A trans woman with long brown hair, side swept bangs a nose ring. She's wearing a burgundy top. She's shown from the shoulders up.

“The first time I went makeup shopping, my friend took me to the pharmacy and I was so terrified. My heart was beating so fast. I was so anxious, I felt like I didn’t belong. I still remember the colour combination that we bought! Now, makeup is such a huge part of my life.

I do it every day for work. First, I wash my face. Then I put on eyeliner with a soft wing. Over my eyelid, I put a shimmery sparkly brown, or a deep red or pink, sometimes I’ll do a very subtle smoky eye. I always, always, ALWAYS wear dark black mascara. I never leave the house without it. I can’t believe we used to live our lives without mascara—it’s really feminizing, but really simple. I can do my basic eye look in three minutes.

Makeup is like my armour. As I transition, I’ve been getting more anxiety about leaving the house and the commute to work on the bus. It’s weird. I guess could actually blend in more without makeup, but there’s something about makeup and a dress that makes me feel prepared to take people on.

Like, if I look good and feel good, then I’ll have the power to make it to work. If someone is looking at me, then I can say to myself, it’s because I look damn good and not because I’m a strange oddball creature, even though it’s probably a combination of both those things. It give me the confidence to smirk back at whoever’s looking.

Makeup helps me look and feel feminine. No matter what I do, I have such a beard, and such a square face, and those things aren’t ever going to change. Makeup unlocks the possibility of what my face could be and what it can do. That’s the beauty of it. And it’s not about passing. When I do makeup, it’s because I want people to know that I’m trans!

I’ve been doing makeup for six years now and it’s taught me what my face really looks like. I’ve always had a hard time looking at myself in the mirror, and doing my makeup helps me know my face. And it makes me feel good, euphoric, sexy. It makes me feel like I want to walk into somewhere so someone can look at me so I can wink at them” — Eve Parker Finley, 24, Montreal

“I was always banned from, and punished for, playing with makeup”

A close-up shot of a trans woman with long, curly black hair and thick eyebrows. She is wearing bright pink lipstick.

“I do makeup because I love it! I think it’s beautiful, I think it’s playful, it should be celebrated, I don’t know why we take ourselves so seriously. If we let children play with makeup, regardless of gender, they would all want to do it.

I don’t have a daily routine. I don’t do makeup every day. I check in with how I’m feeling on a daily basis and how inspired I feel… For me those are the moments when I am connected to the femme that I want to be in the world on that day. Makeup is one part of it; the other parts are hair, dress, accessories.

The eyes are where I have the most fun. The face is such a small canvas, but I feel that there are so many illusions that you can do. My routine is a lot about creating artificial light and artificial shadow. The light elevates something, accentuates something and the shadows allow depth.

Typically, I want to hide my beard or smooth my skin. Then I do one more fixing spray. At the very end when I’m done everything, I do my eyeliner, my liquid liner and my mascara. And then I do my hair.

It’s about adorning my body. As someone who grew up as a little boy, I was always banned from, and punished for, playing with makeup. They say that women only wear makeup to please a man, but I do it to cross the line back into my childhood and allow myself to play in a way that was shamed and not allowed. It’s beautiful and fun. And I reclaim the joy that was forbidden” —Kama, early thirties, Montreal

“People are much friendlier and positive and gender-affirming with me when I’m in makeup”

A trans woman shown sitting down in front of a window. She is wearing a black tank top and pink glasses and has tattoos on her arms.

“Makeup makes me think of freedom because it was the first ‘feminine’ thing I mastered on my own. With makeup I felt a kind of freedom about my face, gender, body. I learned through makeup that I could alter and shift the world.

Makeup made other people see me differently. It didn’t make me see myself differently, but it helped other people along. People are much friendlier and positive and gender-affirming with me when I’m in makeup. This is probably wrong, but because it helps, I do it anyway.

I understand that there is a social pressure to wear makeup, but I enjoy it, so I just wear it regardless. I feel like people shame me for wearing makeup all the time, like I’m submitting to the power of the world. People shame trans women often for doing feminine things and also for not doing them. They shame us for doing stereotypical things because they feel we’re contributing to some kind of oppression, but I just do it because it’s what I feel good doing.

My favourite brands are M.A.C—I’m a 100% M.A.C girl—Urban Decay and NYX. I became really obsessed with doing this ombre eye in a light pink to purple with a lot of translucent glitter, it’s really subtle. I only pull it out on special occasions, and it’s just my favourite look, it does something with the blue of my eyes. I wore it when I first fell in love.” —Gwen Benaway, 30, Toronto

“I feel like I still carry some insecurity around”

A trans woman shown from the shoulders up. She is wearing a black and white polka dot top with a pleated neckline. Her hair is short and curly.

“Makeup makes me feel terror. It’s something that I’m trying to navigate through, trying to get from terror to playfulness and I’m about three-quarters of the way through that journey. A lot of the fear comes from being somebody who transitioned later in life (in my 30s); makeup was one of the biggest challenges in terms of my limited amount of lived experience and knowledge. It felt like I had two decades of catch-up.

I feel like I still carry some of this insecurity around—am I doing things properly? Am I conforming to ‘textbook’ applications and combinations? I’m just trying to find a place where it’s like, less rigid. Where it’s less about conventions and norms and more about self-expression.

One of the first things I did to transition was find someone who did makeup lessons and get them to teach me. I’m still doing the same look. It felt great at first. I got really comfortable with it, and I think at that point early on it was all the things I was looking for. I thought, this is really helping to affirm me. I felt that way for the first six months or so, and then it became a crutch. I was pretty committed to executing it perfectly, and it was an hour of my life every day, blending over and over. I really felt imprisoned by makeup.

To trans girls and women who are coming out and exploring makeup, I would say, make sure you’re doing it on your own terms. Make sure it’s something that empowers you, that makes you feel pretty and the way you want to look. At the end of the day, do it for yourself” —Amelia, 34, Calgary

“I am so there for the butch trans women who don’t see why they need makeup or don’t like it or don’t know how”

A trans woman shown from the chest up. She is wearing a black tank top and has tattoos on her arms. Her hair is long and dark brown and she's wearing dramatic eye makeup.

“My earliest single memory in life involves makeup. I couldn’t have been more than three. I remember coming out of my room and going into my parents’ room. My mom was getting ready for work, and I asked to sit up on the counter and was watching her do her makeup and was fascinated and started putting it on myself. I totally ate some concealer and thought it was a very interesting flavour.

Every day when I get ready to work [as a webcam model], I sit at my makeup station and look at all my materials and decide what I’m going to do. That’s a beautiful moment. I find the whole process very meditative, and on a work day it usually takes me about an hour. That’s my hour of really being present. I’m so focused on it that nothing crosses my mind, my other tasks disappear. I really look forward to sitting down for that hour and being both self-centred and meditative at the same time.

I watch a lot of other trans girl web cammers, and many of them do not wear makeup or wear very little makeup, which surprised me. For me, it comes back to identity. I see makeup as a way to make the features that already exist more extreme. To make your eyes even bigger, your cheekbones more severe. It’s a way to embody gender, but also a specific cultural aesthetic.

At work, I wear makeup that is quite severe and dark as a dominatrix. I have an ‘evil’ aesthetic, I’m a scary bitch woman. It’s about making my brand more readily comprehensible to people in a very superficial way. Camming is all about people scrolling through screenshots, and that shot is your one chance to grab them. What you say with one picture is your one chance to make money that day and build your brand.

I usually don’t wear makeup if I’m not working. I like that contrast—when I’m out in the world it’s no makeup, baggy clothes, big glasses. I wear things that cover me. It’s not because I’m embarrassed about not wearing makeup, but because I’m trying to minimize the ‘poster child for trans women’ effect as much as possible.

I want to encourage trans women to not be obsessed with makeup. Besides the obvious fact that the beauty industry is so tied up in racism and ableism and normative beauty standards, I think that trans women get a lot of both positive and negative reinforcement to do makeup. I want to say, ‘You don’t have to.’ I don’t want people to feel that it’s an unattainable goal, yet they must attain it to be a trans woman. My day-to-day self without makeup is the more real me. I love going out in the world and being a sporty dyke and not wearing makeup, not having that be the thing by which I am found to be hot.

It’s much more fulfilling when people find me sexy because of my personality and the strength I have built in finding myself.

I am so there for the butch trans women who don’t see why they need makeup or don’t like it or don’t know how. I fear for trans women feeling like it’s the only way to be recognized for who they are because we’re more likely to be misgendered without it. I will always see them. I will always see trans women who don’t want to embody normative standards of what a woman looks like” — The Mortal Medusa, 28, Montreal


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