Pls keep reform out of this discussion, this is a misdirection. Many charedi takanot that protect people from improper influences have good social reasons behind them, but this is not we are talking about.
I’ve seen lots of photos of observant Jews from Lithuania to Iraq. Most of them dressed similarly to their gentile neighbors. In some cases, they are dressed more on respectable side. Sephardi “gedolim” sometimes dressed more extravagant, but these were individuals. Most of people worked in whatever jobs they were able to obtain under restrictions imposed on us. Volozhin yeshiva had 400 students. Most Yidden did not expect other Yidden to pay for their learning and did not collect from non-Jewish welfare funds.