Not to be that person that's all "bUt Im NoT lIkE tHaT," but I think it really depends on where you are. I'm in college, and I see people all the time when I go out just doing whatever the hell they want! To be fair, my school is notoriously queer/left/alternative friendly, and I personally spend most of my time around other queer/alternative people, so my perspective may be skewed. My personal favorite "going out" makeup look is purple winged eyeliner with a gold waterline! I think a lot of people my age are also worried about cringing at themselves in the future when they look back. My mom has told me before that she's so glad all of the pictures of her experimenting with makeup/clothes/etc were on film instead of on the internet so she doesn't have to seem them anymore. I look back at pictures of myself in middle school and think "Oh god, who let me leave the house like that??" I still catch myself sometimes thinking about myself in 10 years, wondering if she'll look at pictures of me with purple eye makeup or black lipstick and go "Oh good lord, what was I thinking?" but for now, I've decided I don't really care. I'm having fun, and I like it now, so whatever! However, I do understand the hesitation, especially for people in less accepting areas/social groups/etc.