I approached my conceal carry decision conventionally.

Already had my weapon selected (Commander size 1911), which should be the first decision, and elected to go with a strong side high rise OWB holster.

Admittedly it took a lot of practice to get proficient with this setup, plus a handful of holsters to find the right one.

Lessons I learned were:

- Find a holster than can convert from strong side to crossdraw.

- Ability to quickly remove the holster w/o having to take my belt off is a nice feature. Milt Sparks Axiom/VM II or similar style holsters are ideal once you get used to the snaps.

- Avoid changing your weapon based on the season unless you can maintain proficiency with them. I was tempted to go the pocket pistol route during the summer when shorts and flip flops are my standard attire but I am not bright enough to flip between weapons.