The Chofetz Chaim wore overall-type garments when running his store. Chazal most likely wore clothing appropriate to whatever work they were doing in the days of the Gemara. I don’t think wearing clothing inappropriate for an activity or task at hand is meritorius. In fact, it can border on pikuach nefesh- failing to wear protective clothing when doing manual labor, etc., and even baal tashchis- wasteful consumption, as one risks damaging expensive clothing (i.e. suits) if worn during such activities which can be messy. Do you ever see a butcher not wearing a protective white oat or a painter not wearing the right clothing? Mowing a lawn might be different, but it is the same idea.
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