Hi, I think the first thing anyone should buy is foundation (with spf) there are so many products you can use that are not essential.
If you are young and have perfect skin then BB cream on it's own is all you will need.
Most important thing about foundation is that it matches your skin, you can keep buying them till you luck it, it can get expensive or go to a proper make up store and have them match your skin (recommended) and even then maybe you go get your makeup done at mac, buy the foundation then find out you get breakouts and have to go to another store and try again.
buy a good brush set, you will never regret that, no one looks good using their fingers.
normal day for me is, nude by nature mineral powder and inglot eyeliner
if I want to look good, then nude by nature liquid foundation, then nude by nature mineral powder, inglot eyeliner, napoleon mascara, natural lipstick
The next one I don't do much, is more for photoshoot or night time events. I just look out of place with my makeup at this level were I live.
Mac prep & prime, mac liquid foundation, inglot contouring and highlights, blush, inglot eyebrow filler, loreal (only because I don't have better, but they are quite nice) eyeshadows, use about 4 of them, inglot eye liner, false eyelashes, napoleon mascara, lip liner , plumping lipstick, lip gloss, and finish it all off with Krylon setting powder
I had my makeup done for a wedding, so asked a million questions, took photos of all the products she used, took me months to go to all the stores and get stuff matched to my skin, also went and had make up done at mac store and got tips from them.
Most stores you can pay for a makeup session then they take the price of the session off any products you buy.
I understand it's pretty intimidating for those in transition or that still have facial hair, but high end store I went to had guys and gals working in them and they all had makeup on, I don't think they would judge anyone.
I'm always learning, and there's still so many things I could add, like eyelid primer. I just watch the youtube videos.
I'm friends with a hair dresser also so I've been buying salon quality straightners and dryers, and learning about blow waves, heat sprays, 7 day treatmeants, argon oil , delron and ceramic brushes and trying to get good at that. If you can walk out the door on your own with close to salon hair and professional makeup then your doing pretty good.
I tend to take the side of caution with makeup, better to look a bit subtle then ending up looking like marilyn manson or pennywise.
If anyone has a question I can try to answer, but I'm sure some of these young folk are much better versed at makeup than I am.