I think you're asking for advice, so here's mine on makeup: practice makes perfect.

It is an art, like sketching, painting, or anything else. Even if you find a good tutorial, you're still going to need to practice. Part of your learning process may include an afternoon where you apply makeup, wipe it off, and apply a few more times so that you can really hone in on some things.

Don't be afraid of cheap makeup, especially while you're learning. Once you know what works for you, then you may decide you want to get some fancier products.

Try some nail polish and there's colored chapstick for an easy start, take something with a near natural color.

For clothing you could try a fetish store if you can find one in your area because the people working there have seen everything and so you'll feel safer. They can probably help you. Alternatively you could try a store that has unisex clothing for a first step. And also stockings can be cheap and they are flexible in fit, so you could order those online.

For foundation you'll definitely need some support, so maybe that's quite a big step for you. Because it needs to be the right color for your skin.

Clothes are a bit slower than makeup as you first need t grow your wardrobe. You'll first need to learn how to go shopping, as you probably, like most of us, never got to that before. It's hard to explain, getting someone who knows how to come with you helps tremendosly. But for starters, I'd say imagne how you want to look like, not detailed, but loosly. Take that image, go shopping and find matches. Don't worry about complete fits, that will take a couple hauls. Idk, get what feels right, like what you always wanted, how you want to look like and in a couple hauls, try to match what you've gotten and bam, you should have a couple of fits to work with.

I would recommend against online shopping first, as you need to find out your size first, then go online shpping all you want.(crap stores like amazon and temo, sell crap, best avoid them) If you worry about not passing while running around in the woman section, randomly say stuff like "oh she's gonna like this" or something like that while ppl are in earshot, it helps. Try out high waist clothes, you probably don't have a broad waist like most of us, so low waist stuff usually is a big nono. Check out ICKY, she has some cool clothing guides if you're interested.

Oh yeah and pro tipp, remember the store (chain) you got the best clothes from, you might want to come back.

There is so much more, I'll try to tell if you got this so far....

I don't have much advice, but I'm in a very similar place, and I appreciate you asking and generating discussion.