Ella, I bet you're beautiful. In my opinion this boy is shallow, personality is better over looks. People shouldn't be interested in others just for looks.
I really want to hug you. Make-up, leggings, and thinness are all person choices. If people don't want to talk to you because of that then they are really stupid and need to reconsider their decisions.
Girl, if you want something in life go after it. Try to build a friendship with him--if you haven't already--and then go ask him out! Weight doesn't matter as long as your healthy. I know thinness is a desire, but a little meat on the bones looks just as great as stick thin.