9th grade - I'd sneak a maybelline mascara, the plain one in the ivory colored tube with a gold top, the one that didn't do anything but darken my lashes. Got it in waterproof so even after I washed my face because my mom made me, I'd still have on my mascara.
I also collected a bunch of totally wrong for me colors - usually WnW, CG, Maybelline. Shades of aqua, purple, hot pink, all those plasticky 80s colors that really didn't work my red hair and peachy skin. WHat did I know? Plus I was allergic to everything. Still am, except certain mineral shadows.
For my daughter, since she had skin issues like I did, I tried really hard to help her out - she began using foundation that I helped her pick when she was about 13. Mineral stuff, so I felt ok about her skin. She still uses that brand, 6 years later. She's really good at her makeup, too - skilled with blending and color combos and liner and all that.