OK, shy ones. Time to fly your freak flag and wear something wild.
I'm sort of a Gap dresser, myself. It is simple, quick and moderately priced. What I'm suggesting here is just a little bit out of your box. For instance, would I be able to wear that crazy orange and pink shirt that I got from the thrift shop and wore one time? I liked it enough to buy it but it really does "shout." OK, I'm gonna do it! How about you?
Take a picture of the wild item (it could be as simple as two different colored socks) and/or YOU wearing it and post it on the Flickr site!