Wether or not we care, it is just so unfortunate that society will always judge People based off their appearances, like it's just the usual, some certain attire will attract certain attention when you walk into the room and that's just how it has been wired into society and alot of persons look towards society for acceptance. I mean I have caught myself the same act sometimes and depending on the venue but the truly tour looks can affect how perceive you.
I do think you should dress how comfortably you want to and also be ready to be perceive by others, now I'm not saying you should be bothered or say "look forward to being judged" but then you can't ignore the fact that society will always judge so do with that what you will.
I will always advocate for simple dressing as long as you don't display nudes to the public. This stereotyping and labaling people people by what they wear is very bad, in my country there are places were culture are valued and respect, in the sense that if you see people dress in particular sense, they identify you as such people and I asked, what happen to dressing to look nice, why do we see problem in this but see english wear as normal dressing, like who made this rule.

It's getting worse that once you pierce your nose, you are labelled as a b**ch or slut, if you wear a leg chain, you are labelled the same. Who exactly makes the rules to identify people based on what they see? Just because one person is caught or identified doing that doesn't mean that everyone is doing the same. For many years, dreadlocks were rejected as a style by society, only Jamaicans do dread, but fashion has modernised it to something every celebrity used today, funny world.