Ah, I hadn't seen that one yet, Deborah. I agree that stepping out of our comfort zone once in a while can be a good thing. But will have to disagree with actually being uncomfortable for fashion's sake. I don't find suffering for fashion very stylish at all:-)
Also: when you're not feeling comfortable in what you're wearing (physically or on another level), that often shows too, don't you think (e.g. you keep fidgeting with your clothes, or you're just not feeling super confident about yourself), and that doesn't really help you achieve "the look" either, methinks?-)