“What is the meaning of wearing the traditional “yeshivish” uniform of black and white?”
and
“I guess what I’m asking is: What does a guy’s levush truly represent about him???”
It all starts with “Don’t separate yourself from the community”
Indeed, many of the minhagim of dress came from our holy fathers in Europe. We don’t have reshus to go out from their derech. “Minhag avoisanu b’yodainu”.
A person has to make himself part of the klal. If he doesn’t, you have to understand what the problem is. Is he a baal gaavah and wants to stand out or be different? There are acceptable ways to do that. Is he not committed? Does he not understand the value of sholom? These are big questions to the guy who can’t dress properly or wants to make some kind of statement.
Part of being a frum Yid is making yourself conform. There is plenty of room on the inside for unique hashkafa and personality, but if you can’t dress like a mench, *you* have a problem. If you can’t conform to levush, Torah lo kol shekain?