"If you insist on being able to dress the way you want as a means of self expression then you really dont have anything worth expressing."

My initial reaction was to guffaw at the ridiculousness of such a statement. Expression through fashion and attire is pretty much the entire reason we dont all wear the same thing as each other every day. I feel the exact opposite as you: people who dont dress with the awareness that their appearance is a statement to the world they walk into are missing a massive opportunity to affect their day. How people treat you. How people respond to you. Etc.

But since I'm growing less cynical in my old age, I would care to learn more about your perspective if you care to share.