Not my nails, obvs.
Some (beginner-focused) tips for painting your nails:
Lighter colors and solid colors are easier to work with. Pick a good color or few, you don't need to start too fancy.
Don't shake nail polish, that can mess it up. Roll it slowly if you ever need to mix.
Don't just do the coloration and call it a day, put clear nail polish on first, and put it over the color. That will protect your nails.
Consider getting nail polish remover when you get your nail polish, mistakes are easy.
Put your nails down on a flat surface, clean your nails (maybe with that nail polish remover?), and apply the clear base coat (doesn't need to be perfect). Stroke from the base of the nail to the top, until the nail is covered. It might get on your skin, that's normal, anything on your skin can be dealt with at the end. Let it dry, like you would any other kind of base coat.
Now that it's dry, do like what you did with your clear polish for colors. Base to tip, going from the center outwards. If you can still see through after it's covered, wait for it to dry a little, then do another layer.
Then apply your top coat to make smooth, shiny, and somewhat protected painted nails. Wait for it all to dry (very important), which could as long as normal working hours + commute. Don't mess it up. If you do, you might have to restart on some nails.
Now that it's dry the polish on your skin should act sorta like glue, where you can just peel it off, but if it's stubborn you could use a cotton swab with nail polish remover to carefully remove it (don't let it touch your nails!).
Now you should have nice smooth nails.
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Definitely do the vintage and org, those two are great environments to start acclimating yourself in. I'd probably do a check-in after those two to ask if she'd like to try going to any actual stores in person or if she's content and then follow her lead and bring her to a mall or smth
Regarding sizing, general rule of thumb is a women's size is a men's size +1, so she's probably extra large or in the plus sizes depending on her exact measurements, so anything in those sections ought to be okay I think. Admittedly I am tiny (women's small) so I have little experience with the higher end of women's sizes so ymmv.
General unedited recommendations for clothing: if she gets any skirts make sure she tries them on high waisted (at the thinnest part of her waist, a bit above the bellybutton usually) since that helps with making a femme figure and also just looks good imo, neutral colours are a good starting place but she can do whatever she likes, avoiding 90° angles in sleeves is helpful to make shoulders appear less broad, and I'd recommend pushing her to pici up some accessories along with the clothing, I neglected them for a while but they also really help with feeling euphoric.
Can't help with makeup I only just started doing mine literally last week and I started with goth makeup lol.
Thanks!