It is a generally good idea to try to weat something that you consider unusual for you or even unacceptable. It could be bright red or yellow or orange coat, jeans or hat. It is very useful experience - you will notice that people are looking at you - that very important experience (which couldn't be extracted from books or other way) for shy prople on the way of self-development. And you also will notice that the sky still didn't fall on earch because you're wearing this imposible (for you) hat or coat.
I sometimes wear a bathrobe. Not one I actually use as a bathrobe... Just instead of a trenchcoat. It's ridiculously comfortable, and gets people to talk to me.
