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I do the Hawaiian shirt thing when the temps are above 90. It may look a bit odd on a guy under the age of 60 (I am 46), but not so odd as to draw attention. Wearing tactical or "western wear" would be more out-of-place in my neck-of-the-woods... I see photos of guys wearing jeans, boots, leather vest, and a cowboy hat... It would be nice to dress that way, but I would definitely NOT blend in...
People wear all kinds of things, and 90% of us are not going to please the fashionistas no matter what we wear... and honestly, who cares what the fashionistas think. While it is true you have to be comfortable with how you look, some sacrifices have to be made to concealment and comfort-while-concealing.
In addition to Hawaiian shirts, I also wear a lot of short-sleeve button-down oxford style shirts which I wear untucked with shorts. or a kangaroo-carry armpit carry with the shirt tucked in.
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