I wear the same clothes every day because I don't really interface with the public that much and because I've been doing it since I was a little kid. I got made fun of it a lot in school but sooner or later people came to accept it. If you ask me now why I did it back then, I wouldn't know (or at least I didn't think about it enough to think about "why," I just did it).

If you asked me now though, I'd say that aside from appeasing societal norms, there's no point in changing your outer shell incessantly. Clothes don't really get that dirty after a day or two of normal wear, and changing them all the time seems pointless to me. While some people may brand this as unhygienic, I respectfully disagree. I also don't care if other people want to change their clothes every day, I just don't care to do it myself.

That said, there was a lot more to Steve Jobs than his clothing and habits. I don't suggest anybody change their behavior to emulate him, especially on what I consider a weak argument. If you want to wear the same shirt every day, do it for your own reasons, not because of some conjecture you have on what statement Jobs was trying to make.