I went to my local gun show looking for a replacement front pocket gun, and after some initial dazzlement and confusion with all the neat guns, ended up talking with Marty at the FAO Holster
island, consisting of several tables totally loaded up with holsters. I asked to see a J-frame pocket holster and he immediately asked if I was going to be wearing my jeans. I said yes, and he told me it wouldn't work and made me try it. He said if I'd go to Dockers it would work, but if I wanted to keep my jeans, he suggested a Colt Mustang or Kahr Micro (either one for reliability).
While waiting for my paperwork to clear, I asked to see J-hook holsters for the PM9. Marty advised me to make a pocket holster my primary as it made it easy to develop a constant carry habit. He explained that after selling a friend a pocket holster for his P32, he'd been leaning on him for weeks to put it in his pocket as soon as he put on his pants in the morning. Finally his friend told him he decided to start doing that. Ten days later at 10 or 11 on a Saturday morning, as always on a Saturday morning, he was sitting on the living room couch minding the kids while his wife and her friends went malling. Suddenly, four guys with guns dressed in ski masks and black BDUs broke through his front door. He leaned sideways on the couch to get at his gun, drew it and nailed the first one who fell dead on the spot. The other three ran out. The police caught them wandering around the neighborhood (they'd found the getaway vehicle keys in the dead one's pocket). When asked why they had broken into the house of a "gun nut," one of them replied "Who carries a gun inside their house?"
All of this is a long way of saying that I used to get things all backwards. I'd learn about some cool gun or the other and buy it with the holster as an afterthought. When I left home for the gun show, really I was trying to decide between a J-frame and a Glock 26. But after Marty clearly defined my problem for me, I discovered that the only decent solution was another thing altogether.