Have you ever felt humiliated for looking "poor"?

Well, it's always possible he considered coveralls typical everyday garb in that particular business setting, but I doubt it. He was probably making a statement and basking in the attention. If he didn't care about clothes (manifested by either dressing up or dressing down - but in either case to impress) he would have just shown up in a vanilla shirt and pants outfit.
In 1979-80 at the U.S. Naval Academy, coveralls and ballcaps were temporarily banned as an example of "inappropriate liberty attire". Oh, the drama that ensued. Even a midshipman going out to change the oil on his car had some 'splainin' to do.

Nearly five years later I reported aboard my first submarine. When we got underway, we wore... coveralls, ballcaps, and sneakers.

Nearly three decades later I still can't help smirking when I see the word "coveralls".

My FIL worked with a CBS (union) employee who'd won a cash settlement in a 1970s discrimination/duties assignment lawsuit. 10 years later he was still reporting to work (camera/audio technician) in shorts, ripped t-shirts, sandals, and anything else he could think of (short of a safety violation) to remind management that he was someone not to be trifled with. He never got a promotion but he made it to the pension.
 
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