I have never given in to conformity of clothing, but at the same time I have no tolerance for non-conformists. Everything you do and say will categorize you and will bring assumptions about you and there is NOTHING wrong with that. The “wrong” is when you make OTHER, related assumptions.
If you see me walk around without socks you can assume I associate with a certain group, but you also need to assume that I MAY NOT associate with them. If I see a man without a Keepah and I decide not to be judgemental so I speak in yeshivish talk to him, is that okay? If I see someone in more modern clothes I can’t make judgements about his Torah knowledge or Shabbos observance but I will assume certain things about his social circle unless and until he indicates otherwise.
These are not judgements, they are reference points. Don’t jump on people for finding a reference point unless they give the impression they have abused it with inappropriate assumptions.
I receive food from peoples simchas and redistribute it. If a person comes to me in pants and no hair covering, I may check into their kashrus observance, but I will not assume it is problematic, nor will I assume they are not frum. If a yeshivish person drops off food I may not check into their kashrus observance, but I may also not chose them for advice on ethics or emuna. Everyone is made up of lots of pieces and each piece stands in its own merit.
<pause for breath>