I agree. Also, the same clothes work differently on different people. Some people never look comfortable in a suit, and some people never look at home in jeans.

I guess it all comes down to the role that you are playing, and what you are communicating. Clothing can give you an edge in some circles, but it's contextual and only part of the equation. In a meeting or presentation, I tend to wear black or dark gray with dark jeans, and never logos. I wear that a lot outside of those occasions too. By wearing dark colors and no logo, I am comfortable, and my clothing isn't so rebellious that it can't easily fade into the background. If someone is really hung up about it, then that's probably a good thing to get out of the way.

A bunch of the richest financiers/bankers are known for wearing swatches. I don't know who started it, but it has become a trend. From what I have read, they wear cheap watches to communicate that they can.

Also, I think it is important to point out how masculine this whole thing is. Woman have to approach it from a whole different and complicated angle, and I think variability in men's professional attire is a good thing from that perspective.