It's weird, I never used to wear skate clothes but in the last year or so I've started to. I like wearing shop clothes, it's a good way to rep cities and support shops. Have a few Palace shirts as well.
When I first started skating I wore skate clothes, but then quickly felt uncomfortable wearing them when I'd go out for a session - like I wasn't worthy to be wearing them since I really couldn't do much. Or that I was trying to look like I was sponsored. Or they'd get weird looks and questions, like with a Ghetto Child tee I wore. I would rarely wear them as a result. Then when I would get older, I wore plain, inexpensive gear. I just don't care now, or maybe I'm comfortable enough with my skill set.