I’ve never been much of a makeup person. The women in my life have never been much in the way of makeup users, and while I did have a tiny amount of experience with it during my brief stint in drama when I was in a play in 7th grade, that was the extent of my expereince. So for me, exploring makeup isn’t just a simple thing: it’s a brand new area of experience.

As an adult, I’d actually thought about using makeup even before I was thinking about drag. Several years ago, when getting into conversations about streaming, I was chatting to a female streamer who was a heavy user of makeup. She mentioned that many guys who are streaming would benefit significantly from using makeup – for everything from blemishes to getting rid of the ever-present bags under their eyes. Even years later, this particular sentiment of makeup as a tool for achieving a look stuck with me.

Even with that in mind though, I had never actually given makeup a try. With no experience with makeup, I have to start from scratch – and starting from scratch with makeup is an intimidating thing, especially when you’re a guy! My first efforts were to try to get started by watching YouTube tutorials, but I wasn’t really successful there. One of my biggest problems was that I found many YouTube tutorials targeted at men to be extremely… extra. “Drag makeup” has a meaning, and it was nothing like what I was looking for!

So, I figured the only way to get into it was to try for something super basic: no eyeliner, mascara, or eyeshadow; no blush, contouring, or highlighting. My goal was simple: foundation and lipstick.

I started using tools on the make up websites to try to understand a look that would work for me. In particular, Maybelline has a virtual try-on tool for lipstick, eye, and face shades that I used to experiment with different colors. One thing I quickly noticed is that a femme lipstick looks a bit odd next to my unshaven face, but it still gave me a bit of an idea of what looks I could go for.

Side-by-side comparison of four lipstick shades on an unshaven male face

After playing with it a bit, I decided that what I wanted to try was a bright color on the peach/red side of things: I wasn’t interested in the dark, gothy look that works so well on other folks. I made my purchases – a single lip color and a basic foundation, plus a beauty blender – at a local drugstore.

My initial attempts were… not effective. A couple different things happened:

  • The lip color I bought ended up being too “neutral” for me; I already have relatively pink lips, and so adding a pink color didn’t end up adding much color to the look.
  • I learned that applying lipstick cleanly is really hard. (For all those of you out there who make this shit look easy: well done.)
  • While the foundation helped a lot to neutralize the variations in skin tone, I still had a blueish tint around my lips – the result of masculine facial hair – and needed to find a way around it.

To deal with the blueish skin tone problem, I was able to go back to YouTube and find some helpful tutorials. This particular problem is a common one for trans women and drag, and I found a handful of useful tutorials addressing it. (The term of art is typically “beard shadow”; you can watch one of the tutorials I did in order to learn more about.) The key is to cover the shadow – which tends towards blue – with an opposite color on the color wheel – an orange color – in order to neutralize the effect, then cover with foundation.

In addition to this, I also went with a more vibrant lipstick color – a bright red – and a lip liner in the same color, to allow me to get a more precise line on my lip outline. This latter ended up being extremely useful for me, though I still have no idea if this is a normal usage for anyone else: By defining clear lines along the lip using the lip liner, I can then “fill in” the rest using lipstick, and get a uniform look that follows my lip line.

In the end – with a combination of an orange to fight my beard shadow, a brighter lipstick, and a lip liner, i finally got a look that I was pretty happy with.

Close up portrait, focused on a person with blond hair and bright red lipstick

During this process, I had the help of several friends who were giving me advice, feedback, thoughts, and just a general space to express myself. Thanks especially to SnapClickKat for her support.