You are on target w the polo shirts & Hawaiian. Try them on w/ your carry rig. Don't guess. If there is a seamstress in the family get her to square the bottom of a taylored shirt. Take the high point on the side as the length & make a square tail shirt out of your favorite. I have several & they work good for IWB.
Vest in the winter for OWB.
Shorts or jeans?? just have a good belt & all is well.
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