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I can see how that discussion would come up. Some sketchy people wear baseball caps. Thugs, gangbangers, trouble makers, hooligans, whippersnappers... but you never see a guy in a suit wearing one consistently (the one guy that does this is pretty low class).
I wear baseball caps all the time. I have about 30 of them, around 20 are still of good quality. I remove all stickers as soon as I know it fits.
I played baseball for 12 years or so, that was what started it. It turned into a fashion thing, I guess, but my eyes are pretty sensitive to light so hats are essential for me. I wear one at work everyday to keep the light directly over my head from giving me a headache. Almost all of mine are simple authentic caps, normal height, not turned to the side or backwards, slight bend in the bill. Never understood why people wear hats backwards....
What about women? Lots of women wear them too. I don't handle bright light well, even with glasses, so a cap keeps the sun out. I do a special stitching to go on some of them. One has the symbol of this secret organization in a story I'm writing, a rose like flower. It looks neat and it's personal. Shading yourself from sun especially with glare matters and the baseball cap is perfectly designed to do it well, so why not wear them?
I think it's completely inappropriate in some settings: a funeral! (and yes I witnessed this and it was someone certainly old enough to know better), in a restaurant (other than a sports bar, fast food joint, etc.), church, whatever other "formal and/or "serious" " occasions.
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