Loaded question for me, as it depends on what gun I choose to carry, and as I carry concealed, it can also depend on my clothing for the day, activity or what I am doing for the day. Usually going to and from work, out and about: I go with the G43, or the P938. RAMI and CZ75 also, but not as much as size factor. (Pic below of P365, CZ-75, PT-111, G43)
Factors (in no particular order) that can impact why a person carries a certain way (feel free to throw out other factors):
Function/Dependability
Concealability
Comfort
For me function and concealability are important, as I mainly carry AIW. If I was going for more comfort I would wear the urban digital holster in picture (3 different holsters for G43). I usually wear shorts/t-shirt so I tend to go with the red holster as the profile is super low. The black holster more comfortable than the red holster, but creates a larger footprint.
I also do a lot of running, and still trying to find the right set up for carrying EDC, definitely will need to find the right micro-compact and some way of carrying it while running 6+ miles.

