Firstly, all humans wore some type of head covering and jacket as basic code of decency, which in Judaism translates as “derech eretz” or menchlechkeit (which is kadma latorah). The alter of slabodka specifically emphasized proper dress as part of his overall training in gadlus ha’adam which was also because he felt yeshiva students at that time were looked down upon and only university students gained approval (besides the reason mentioned by cantoresq). In America, upstanding humans wore hats until JFK removed it during the 60’s – the days of defiance and decadence (he actually wore one for his inauguration but subsequently frequently removed it.) The downgrading of a basic mode of dress is not seen as a change in style; rather it is a lack of style – much as shorts aren’t a change in decent style but a further relaxation of societies standards. Therefore, Torah Jews (whether they learn in yeshiva or not) should maintain the basic code of human decency. Why many people don’t is the same reason they don’t do many things they should, in part bec of the influence of society (yes even “insulated” communities are affected by gashmius and taavah). If anyone can effectively explain the white shirts part, I would be very grateful.
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