Mine's probably not very interesting but I'm really digging reading through everyone elses!
I grew up on food stamps and then we became comfortable lower-middle class, still around there as well. But in the area I'm in that's pretty normal, I grew up in the woods lmao. (The only people with "real money" in the area are tourists that come to stay on the lake, or newer implants to the area...anyone that's been here for like ten years is lower middle class with a sprinkling of middle middle class, aha)
I started playing with makeup for fun around 5 or 6 like most kids that play dressup because my mom owned a salon and would bring home testers in the colors that didn't sell well (They used to stock Trucco, I still have a bunch of the eye shadows even though they're like 15 years old. Whoops.) Other than liking to watch my mom do her makeup in the morning and playing dressup and stuff, I was a pretty rough and tumblr kid and didn't care about wearing makeup unless it was a silly flavored Chapstick until I was maybe 11? I got a decent scholarship for a private school in sixth grade, and a lot of the girls there wore makeup - it's also when my skin started going to shit. I was really insecure because at school EVERYONE knew who the five kids that were there on scholarship were, and we'd get shit for being "poor" so I tried to fit in as well as I could and tried to somehow make myself "prettier". (Uh, sorry my dad doesn't have a private jet!) I started wearing makeup regularly (and with more skill, barely) in seventh grade when I went back to public school because I wanted to wow all of my old friends I hadn't seen for a year or something, I don't know.
As far as social groups go...from middle school on I was one of the weird/gothy/emo/alternative/juggalo/stoner/general outcast-y kids, which either meant the other girls in said outcasty groups didn't wear makeup because they were too stoned to give a shit, or lots and lots of $1 WnW eyeliner that they'd shoplifted from the grocery store. I was one of the only people in my grade that I knew that wore a full face in middle school (Hello, bad skin!) and have always always always done really heavy eye makeup. I guess it reflected the "group" I was in cuz my makeup was just as out there as I was. (Though I didn't really subscribe to being in any group, I missed a LOT of school those six years due to my health and would just practice my makeup for going to a million appointments and keeping up with my school friends on MySpace by showing them that my face still existed.)
Phases....well. I've worn winged eyeliner since I first started wearing makeup. My makeup as a whole is still pretty "alternative" with daytime looks that really shouldn't be worn in the daytime, and overdrawn pointy lipstick outlined in black if I'm getting fancy. I got picked on a lot from 6th-8th grade for my makeup which probably just caused me to wear more, but by highschool I stopped giving a shit about if people thought my makeup looked weird (as opposed to using it to attempt to fit in in sixth grade) and that's still true for me. I just wish I could implement my overuse of Loreal HIP loose pigments, but they don't exist anymore.
My mom was always very willing to help me with makeup because it boosted my confidence or at least made me a little more comfortable with myself (skin-wise, if I was really broken out she'd help me figure out skincare and how to cover things properly and take care of myself) but also would constantly ask me to tone things down (as she should! I don't care if you think you're hardcore in ninth grade, you're not wearing black lipstick to Applebees!) but always liked that I used it as a creative outlet. My dad never really had a huge opinion outside of backing up my mom, but would oddly enough help me with color schemes (still does from time to time) if I asked. My mom bringing me up super exposed to the beauty world definitely impacted my relationship with makeup if even just for the fact that I learned how to use it much younger than most people I knew.
My relationship with makeup and self esteem is....strange. I don't feel absolutely awful without it (unless I'm having a bad skin day, which luckily due to some of my other health stuff is becoming less frequent unless I'm hormonal or slather something awful on myself) but if I'm super nervous or something I find a great deal of comfort in being able to just kind of paint another crazy ass face on to hide behind. I'm still not super comfy with more natural looks on myself mostly because I've never worn them and whenever someone else has done them for me they look really out of place to me, but also because if I'm going to go all the way and do my makeup I'm used to almost wearing it defensively.
I think my opinion on makeup in general is freakishly positive, I've helped and encouraged a bunch of my friends when they were uneasy with it and that makes me feel good. (My best friend of 6 years didn't wear makeup the first four that we were friends, she asked me about skin stuff and how to wear eyeliner, and now she does that whole "wings and bold lips" thing as her power look and has thanked me for helping her confidence using makeup which I think is really rad.) I think I get that from my mom, cuz she always would talk about how good she felt when she'd give someone a new hairstyle, brought someone out of their comfort zone beauty-wise or did a bride's makeup and they loved it. I've always felt that the beauty industry is pretty fucked in the fact that it makes people think they have a million problems that need to be fixed via buying whatever product, but I've always loved makeup as a form of self expression and something to have fun with and that out weighs the bad for me.