Everything I wear has to be very comfortable. As a kid, I refused to wear jeans because they didn't feel good to me. The colors and/or prints of my clothes clashed a lot too and I used to get mocked by the other kids for it, but it wasn't until junior high that I starting being really aware of what I was wearing and how I was being judged for it. So I wore mostly black through high school because it was easier than choosing anything and I also started wearing jeans to fit in.
Now, for work, I wear a baggy men's button-up shirt, with a tank top underneath, and jeans. I still hate jeans, but the alternative for work would be slacks, which I don't like even more. As soon as I get home, I change into a loose men's t-shirt and sweats. If I have to go out again, I'll wear the t-shirt with jeans. I only wear athletic shoes. I have 2 pairs of identical jeans and most of my shirts are navy or dark grey.
Sometimes, I feel like I should try to get some different colors so I don't look like I wear the same clothes everyday, but when I go shopping, I generally still buy the same-looking stuff. When I do talk myself into getting something different, I never wear it because I feel like it is too bright or attention-getting, which makes me uncomfortable, and it ends up just sitting in my closet.