It’s complicated … when I was a teenager and didn’t know I was a woman / trans, etc. - every few years I would try makeup again, and every time I would be so upset and disappointed in what I saw in the mirror, it would make me swear off feminizing at all for even longer.

This made me think I wasn’t trans because I didn’t like how makeup looked on me. Now I know I was feeling acute dysphoria when I looked in the mirror, and that the makeup created a clash with and emphasized my masculine traits, which was causing distress.

But at the time, I just thought makeup made me look ugly and I hated how I looked, and since makeup is feminizing and I assumed a trans woman would feel affirmed and happy with makeup, that I must not be trans or a woman, so it must be something else (a fetish, or just nothing).

Decades later, after I socially transitioned and realized that I really was a woman, early on I still struggled with makeup. What helped was to go to a Sephora and get a lesson - basically you pay to sit down and have a makeup specialist color match with your skin and pick out products for you to try, and then they teach you how to apply the makeup.

It was night and day, the results were great and very feminizing, and I felt so happy. What I didn’t know back when I was younger is that makeup is a skill, and unskillful application of makeup can make you look worse or even less feminine.

So my whole attitude and perspective on makeup changed dramatically - instead of seeing it as something that would make me ugly and emphasize my masculine features, I saw it as a tool to combat my masculine features and to feminize my looks. This also made a tool against my dysphoria.

One day, my face was all puffy and red the day after a face laser session, and what I saw in the mirror made me so distressed that I started to spiral into an acutely suicidal moment - and my amazing partner sat me down in the bathroom and applied foundation to cover up my red and puffy skin, and hey - it actually worked. I felt better, I calmed down, and that was a day I realized how powerful makeup can be, and how crucial it is as a tool. I don’t think I would have gone through with ending my life that day, but it certainly helped me recover from acute distress.

So from then on, I developed and maintained a respect for makeup as a pragmatic and life-affirming tool.

I spent hours watching youtube makeup tutorials, especially for how to use makeup to feminize (I often like to share the Samantha Lux feminizing makeup tutorial video), and started to do makeup regularly to help build my skills. Especially after the Sephora lesson, I tried to repeat what I had been taught. I also had women in my life who sat me down and showed me the products they used and how they applied their makeup, which was wonderfully affirming, but also extremely helpful and practical. They even helped me come to cope with applying makeup ethically - I always had “feminist” misgivings about using makeup (I felt it was like a betrayal to women to capitulate to the male gaze, etc.) - but instead I learned to view makeup increasingly as a social tool, as a way to fit in, to help my self-esteem, and I recontextualized makeup as something mostly for me than anything like trying to look appealing to men.

So, early in transition I basically put on a full face of makeup any time I left the house:

• I would pluck eyebrows
• then use a facial cleanser or washcloth to exfoliate the face
• usually I would then shave (if I hadn’t already), at the time mostly with a straight razor (yes, like an old-timey barber in the movies - it’s not the safest tool, but it’s a close shave and it’s frugal)
• when I really wanted to glam up, I would use a sugar scrub to exfoliate my lips as well (makes them smooth, really nice for applying lipstick)
• I would put on a base layer of cosmetic sunscreen that was formulated to act as a makeup base layer (not tinted, not greasy, it just dries on the skin and is great - there are so many great cosmetic sunscreens now, and it’s something I recommend anyone wear every day before they go outside, because it’s the best thing you can do to prevent sun damage that causes the skin to look older)
• I would use foundation or concealer on any pimples or rough areas that needed to be smoothed out,
• I would use contouring to diminish my receding hairline, my jaw line & chin, to hide / reduce the neck area under my jaw / chin, and to raise my cheeks.
• I would apply a small amount of blush to help add a little dimension and situate the cheeks in that raised position.
• I used highlighter to also draw attention to the eyes and cheekbones, and to help narrow the nose (there is a contouring technique with the nose where you put a thin line of highlighter down the center of the nose, then apply a bronzer or darker contouring powder to either side of that line and blend it in so the nose appears less broad).
• I used eye shadow to create a smoky effect, and I would place the eye shadow in a way that raised my eyes and worked against the male-patterned downturned shape (“puppy eyes” shape).
• I similarly would draw eyeliner higher up and start it around half way on the lash line to help raise the eyes further.
• I would use a lash curler because my lashes are too long and tend to droop down rather than point up like sun rays - this is another way to “raise” the eyes; then apply mascara.
• on fancy occasions I would use an eyebrow gel to brush my eyebrows together and hold them in place (so they don’t get all crazy & unruly, and stay neat and looking pretty)
• and I usually liked to use a light pink tinted lip balm on the lips, because drawing attention to the lips detracts from my eyes, and draws attention to clocky aspects of my face like my chin, jaw, and the proportions of my lips and space between the nose and my lips, etc. - I basically never wear any dark lipstick at all, only nudes and pinks that are light and neutral, and usually I prefer to stick with tinted lip balms that keep my lips hydrated and won’t get on everything my lips touch

Usually, I put on a special playlist of music when I’m putting on my makeup. It’s one of my favorite things to do, for sure. I often find that I enjoy my girly music and putting on makeup even more than I enjoy the event I got all dressed up for.

Here are some songs on my playlist to give you a general vibe and sense:

• Lauren by Men I Trust
• Fire for You by Cannons
• Hanoï Cafe by Bleu Toucan

Most days now, I pass and don’t need to wear a full face of makeup. I only go all out like that for date nights and special events.

Most days now when I go out my minimalist routine is:

• wash face, clear crud out of eyes, etc.
• pluck eyebrows
• use a women’s electric facial hair remover tool to beat back whatever facial hair is still there (because I’ve had enough hair removal that I don’t have a beard shadow anymore, and the few stragglers that remain are not that visible, so it’s OK to just use one of these convenient electric tools rather than pull out my straight razor and strop)
• apply cosmetic sunscreen (I use different ones depending on the day and purpose; exercise calls for a different face sunscreen than going to the bank, etc.)
• apply tinted lip balm
• curl lashes
• apply mascara (sometimes I skip this if I’m short on time, my lashes are dark enough I can get away with just curling them and moving on; but I do look a bit plain, then)

Usually I’m doing this in a rush, so I rarely listen to music during these kinds of makeup sessions, and they’re more mundane.

In terms of what I see in the mirror: without fail, I underestimate the way makeup improves my self-esteem and increases the odds I will be happily surprised at what I see in the mirror. It’s not a silver bullet, but it does tangibly help.

This actually became a tool I would use even on days I wasn’t leaving the house - taking care of my hair and doing makeup is something I did early in transition just to feel better, even if for no other reason.

Applying makeup does have a downside in that I spend a lot more time looking at myself in the mirror, and that can easily get out of control and turn into self-scrutiny and a down-ward spiral. Today I had a date night, and I did my full glam makeup with music playlist and everything (today my playlist was more Rihanna oriented 😅), but I kept thinking I was so ugly and that the makeup was so pointless because it’s like putting makeup on a pig, etc. - I just felt too ugly to bother with.

But, then after I was done, and my partner oo’d and awe’d over me, I started to feel better, and there would be times I glanced at myself in the mirror and could see I was pretty. As usual I find I like what I see in the mirror when: 1. under low light conditions, 2. when I’m further away and I can’t see every little detail, 3. when the light is warm and forgiving (and not harsh, blue, fluorescent, etc.).

So, it’s a mixed bag.

Some days it’s just better not to look in the mirror, and to just dissociate from my body entirely - like rest days. Other days, particularly when I have to leave my house, I find it’s worth bothering with makeup.