i dont know so much about clothing, but i could give you a few tips on starting to wear makeup.
brand-wise, it depends on your skin sensitivity, and what you prefer. Heres a tip: before purchasing, try it on, see if you like it or not.
Wearing makeup can often clog up your pores, so if you want to start wearing makeup i would consider getting into a skincare routine, this also depends if you have bad acne or not, but i highly recommend just using moisturizer and toner and optional scrubs, etc... dont jump straight into it, if I were you i would just ease into it bit by bit.
thats the same case with makeup, i would just ease into it. start by using little amounts of lip balm / lip gloss,
and then start into mascara, eye liner and if you want; blush and foundation, if you want a lighter option, i would go for powder.
the choice is yours, but these are just a few little tips.