I wasn't allowed to wear much makeup when I was growing up (I also went to a small private Catholic school), except for special occasions like dances or plays where I had to wear a lot of makeup.  I loved dressing up for the plays because I got to see what it was like to wear a ton of makeup and have it be okay – it was like turning into a different person!  Sometime around mid-high school I started experimenting with concealer and eyeliner.  But I never had problems with my skin so the only thing I ever really needed to conceal was dark circles under my eyes. My mom wouldn't let me out of the house if my eyeliner was too noticeable.  I would look at other girls who wore more makeup and wish I could copy their "look," but for some reason whenever I would try I would feel really self-conscious about it, like I didn't look like myself and somebody was going to notice and call me out on it.  So I never really wore much makeup until college, but by now I feel like I've really personalized my routine.  For instance, I only ever wear concealer under my eyes and nothing else except transluscent powder goes onto my face.  And I still wear eyeliner, but more heavily and only on my top lashes and the very outside corners of my bottom lashes (I never draw a line across my whole bottom lid unless it's for a show).  If I'm really into it, or I'm going out at night, I'll do eyeshadow and mascara and I'll fill in my brows a bit, but I never cake on heavy makeup. 

I don't need makeup to feel pretty; if I've been getting sleep, drinking water, and taking care of my skin, I feel good without it.  But there are days that I wear it because I don't look presentable, and this is usually due to dark circles under my eyes.  And even then, the main reason I put it on is because if I don't, everyone will ask me if I've been getting enough sleep, and that just gets annoying after a while – especially if I did actually get rest.  As said earlier, it's more about packaging – I feel more put together and professional when I'm wearing it, and that's what I feel good about. I'd like to feel that put together all the time, but the other big reason I don't wear makeup sometimes is laziness or lack of time.