Always_Ask_Questions,
“You mentioned it as something you students equate with becoming more observant.”
No he didn’t. He said it was something some of his former students would approach him and ask. It is entirely your uninformed assumption that the reason for the question is that this is what the kid equates with being more observant. Every kid I know who has chosen himself to don a black hat and jacket is doing much more – davening with more kavannah, saying krias shema slowly while reading each word from the siddur, being careful with mitzvos, shteiging more, etc. They look up to yeshiva men. They want to emulate yeshiva men, to do what they do, and wear what they wear. So why is the kid asking about the hat specifically and not the shteiging or davening? Because it’s the hat that makes people freak out, and thus feels confusing and controversial. So, quite bluntly, it’s not Avira who’s causing kids to come with hat shailos, it’s you. Those who are big and bad on fighting for the kid who doesn’t want to wear a hat should stop stifling the kid who does.
“Some seem to be upset with nominally observant Yidden because they are not enlightened enough; others – with people who think dress is the enlightment people need, ortho-prax or not.”
And some people give kollel learners such a hard time that they feel embarrassment when asked “what do you do?” Some people (Ashkenazim) seem personally offended if they hear a Yiddish word or expression. Interestingly those who do this tend to fall within a set of identifiable clothing choices. Should I see this as people being imperfect people, or make generalizations about all people who wear those clothes?