A transgender female, whether a transwoman (one who wishes to live full time or part time female) or a cross dresser (one who fundamentally still identifies as male but finds some relief and comfort in dressing as a female), needs to understand how to use makeup. The world has become a much more tolerant place, but is generally not so forgiving that an overly cross-dressing male can walk down the street and receive no harassment.
I’m going to use the term TG female to describe both categories although there are some differences in their purposes. Transwomen generally want to blend in, they want to go through the world perceived and living as women and therefore not stick out. Most cross dressers I’ve met are only able to express themselves on rare occasion and generally want to stand out, but generally aren’t doing so in a public forum. I confess to having much less experience with cross dressers, and the reader should understand that these are broad categorizations and that TG people can flow between them or may well encompass aspects of each.
Cis-gendered females (women who were born as female) generally get to learn about makeup from their female relatives and their friends, and what’s more have this enormous societal grace period where they can look like raccoons with super overdone shadow, liner and mascara and super carmine red lipstick and just amuse older women who remember not knowing how to use makeup in a subtle and appropriate fashion.
The real problem when you’re starting is that the truth of makeup and what you need to get by are opposed to one another. Ideally you want to be a minimalist on makeup, enhancing what you have and minimizing those features you’d like to not be so obvious. However, when you’re starting you’ll likely have a somewhat visible field of stubble on your face no matter how hard you shave. This is a dilemma.
I’ll leave it to the reader to do a search in Google or on YouTube. There is a lot of good advice on covering up beards. Just know that if you’re out and about you need to plan. You don’t want to shave at 9am and do your makeup and go out at 3pm when the stubble is showing.
This makes getting laser hair removal and electrolysis very important for transwomen. If you have much dark hair and have light skin, start with laser, it will get more hair faster and it targets the hair that really is hard to cover up. Then work on the white and gray hairs. It will take some time and a bunch of money. There are a number of anesthetic creams out there, ask your tech what they recommend. You definitely want to do what you can, it will still be uncomfortable.
For me at my stage of the journey (about 2 1/2 years of electrolysis, 2 years of HRT) I have very little left of my facial hair. What I do with makeup depends on what’s going on, but not using it is a popular option for me.
Work – for work I usually put on a medium foundation, blush and mascara. If I use lipstick or gloss it is something very neutral with respect to my skin tone and lip color. It just “highlights” my lips. If I have time I’ll use some brown, black or purple liner with or without neutral eye shadow. The result is fairly subtle and it is supposed to be.
Weekends – Nothing, not a stitch of makeup. I’ll use lipstick or lipgloss if my lips are chapped, but otherwise nothing.
Events – If I’m getting dressed up then I’m more likely to put more obvious makeup on, mostly that means the eye shadow would be more pronounced and I might actually fuss with my brows. The lipstick might be a bolder color and some bronzer to contour my face.
If you have questions about applying makeup or brand reviews and such, YouTube is your friend. You can learn an awful lot from it. It isn’t as personal as your mom, but it’s available 24/7.