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Here are some pictures of a hand made holster my pal just bought me. It fits my Kel-Tec PF9 like a glove, but I have two questions. What is the best way to carry this? I've never carried IWB... Secondly, how can I soften the leather, or, will it eventually loosen up as I wear it more often? Thanks.

It looks like it would work for strong side hip, ie... 3-5 o'clock.

That is an outside the waistband (OWB) holster. So, it will not work for IWB. It may work between your belt and your pants, depending on belt length. One consideration with this hoster design is belt tension can have a great effect on how tightly the gun is held in the holster

I'd suggest wearing it around the house and practicing your drawstroke, with an unloaded gun of course. That will help the break in process. Leather can vary greatly in how much it stretches.

What part did you want to be softer?

That is an OWB (Yaqui Slide type) holster.

I wouldn't recommend using any leather softeners on it.

It will eventually begin to take on a certain "shape", but you don't want it to get appreciably softer.