"The Man" is the hippie-title for people adhering to the organized corporate world we live in.
Keeping in mind that we always communicate.
I don't dress to be different. That matters not.
I dress to communicate who I am.
Congruence.
Ultimately, I dress to look as close to my ideals about what looking good is, I work out and eat mostly vegetarian to optimize my health and to look good (looking good is equivalent to looking healthy in my view).
These are the constructs of physical appearance. So the way I dress should, in essence, show off my body, to some degree, and how healthy it is.
To some extent, I adhere to social standards about what one should look like, and I don't go in direct opposition, just to be different, which usually leads to resistance (e.g. the Black Metal uniform, with black clothes and spikes, long hair, etc.)