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I wish I could help with OWB. The best advice, like was said, have a good gun belt.

For me, I went to the gun show and tried a whole bunch of holsters. The dealers are quite helpful and allowed me to try them on. This might be the best way to test drive a couple.

Good luck!!

Okay, can't help you with OWB or overalls. There are some OWB folks here that will be along to give some feedback.

What equipment do you have?
What position do you like to carry in?
Do you tuck in your shirts or leave 'em hanging