Not too long ago, I was at a gun show with a couple of friends. At the clearing barrel, one of them cleared his heater and went to reholster it, but the holster had collapsed somewhat. The gun wouldn't seat and so he tried again, causing the holster to collapse a little more.
With the rest of us standing there watching, he kept trying to force the muzzle of the gun into the holster in what had to be an intensely frustrating exercise. Being able to stow the gat without looking is a fundamental skill if you carry the holster behind the point of the hip, and with people standing there watching as your gear defeats your attempts at performing this task, it's easy to get flustered.
Thing is, this was no novice; far from it. He'd been shooting pistols since he was big enough to hold them and had many hundreds of hours of formal gun school. And this wasn't crappy gear, either; it was a horsehide Mitch Rosen rig that had just apparently decided to give up the ghost after probably well more than a decade of carry.
That leads me to this post (which also harshes on the holster type I love to hate most.) I've personally come around to carrying kydex holsters IWB. Some folks argue that "Kydex doesn't bend to conform to your body!" I don't really get that, because my holster is only about as wide as the gun that's in it, and the gun itself doesn't bend to conform to your body, either, no matter what you wrap it in.
Quality gear is important. Regularly checking that the quality gear is still in good shape is important. Do the important stuff.