Ooo girl, I could talk about makeup for hours! I watched so many YouTube videos for years before finally starting to practice last summer. I started working at a clothing store last July, and started experimenting with both women's clothes and makeup for work. I started small, and I wasn't decidedly trans quite yet, so I'd wear foundation and concealer, used a brown eye pencil, things that would make me look more pretty boy than woman. They say to start by using the canvas you already have.
As I went, it just sort of took off, I think because I'd been wanting to wear makeup for years and I finally had the opportunity to do whatever I wanted with it. Before I knew, I was contouring and eyelining and shadowing and wearing false lashes. But again, this was at a clothing store, so it made more sense for me to do all that.
I didn't know how to do simple makeup for just being out during the day or at a massage gig (I'm a freelance massage therapist) until I did the full(est) face first. I had to go big before I learned how to tone down. And spending an hour on my makeup when I'm going to be rubbing people who are face down really doesn't make sense. Something really oddly wonderful though, is that my face has a more feminine quality with less makeup because I started to act more feminine because of the full routine. I started to see myself differently, and wasn't forcing myself to cover up, but enjoying bringing out what I already liked about my face.
Lastly (for now lol), I started wearing makeup months before taking any hormones or finding a new name, etc. I needed to practice looking like a woman to the fullest extent possible, to give myself room to come to the middle. I still glam it up when I have the time or the occasion calls for it, but I have a better view of myself because I gave that time in between to see a snapshot of what I might look like in the future.
If you'd like, I would LOVE to chat with you privately and talk about any questions you have, products to start with, how to start slowly so you aren't overwhelmed, etc. I remember the beginning because it wasn't long ago, and there were days that I would wipe everything off because I hated what little skill I had at the time. So, no judgments, and it's actually a lot of fun for me to help that way. Also, if you were to go to my profile and look at my topics, I have pics on #13 from January and #1 from last week. What a difference a few months can make!
Be well,
Aria