Earlier quoted context omitted.
so... break it down for me. What social advantages do I gain by varying my clothing day-to-day? (I mean, I understand the advantages of fitting your clothing to the situation; that's not my question. My question is, if the situation calls for a suit, what's the problem with wearing the same style of suit every time the situation calls for a suit? the same style of T shirt when the situation calls for a T shirt, etc..…
If I wore the same clothes everyday (steve jobs style), I'm pretty sure my girlfriend would start to complain and people would start to notice. I don't think it's a good reputation. You're that uninteresting guy from the office that always wears the same clothes.....
But, uh, yeah. I mean, I'm still thinking that the opposite is more true. I mean, fictional characters often do exactly the same thing[1], really for similar reasons. And, as you point out, it's somewhat unusual, which is not boring, even if it might be offensive to some people.
On being more interesting... heh. I should re-arrange my closet like the tvtropes photo below, and post photos.
[1]http://tvtropes.org/pmwiki/pmwiki.php/Main/LimitedWardrobe