It isn't just your shirttail that does this, with mine I have to be careful every time I put it into the holster to make sure it clicks in firm/positive once it has it is good to go (I do catch shirts in it all the time too). I hang mine from my pocket lip - not my belt, if it hangs on my belt it digs into my side (too many pizzas i guess). I do love it though, looked at a few and settled on the Defender.