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I found a company called Ace Case, I ordered a couple of holsters from them. One of them is called a "Tuck-able". It allows a shirt to tuck in between the gun and the clip, making only the clip visible. I'll let you know when I get them.
I iwb with a comp-tac minotaur neutral with a kahr cw9 and can tuck a botton down at a 2:10 position BUT your buddy may need something very different. Body size helps or hurts too.