As someone who loves finding my own personal fashion, op-shops, and making beautiful, comfortable clothes, I loved this TED talk.
I often get complimented on my favorite pair of cowboy boots. They are beat up red ones, from the 70's. They need to be re-soled, they're scuffed, they stand out. When complimented, the person often follows up with a wistful, "I could never wear something like that." I always tell them, "Sure you can. If you see it and love it, why not? The only thing stopping you is you."
Try it out. Buy that piece you don't think you have the guts to wear, that you don't think you could 'pull off'. At least give it a try before writing it off!
Go out and find something fun to wear!