I think I have a 4 drawer filing cabinet full of holsters. And 3 pair of shoes to my name.
I use different holsters for different occasions, and for different guns. Wore a 4 inch 357 in a strong side hip holster for years. Shoulder holster (upright) for a 1911.
Food for thought- damned hard to draw when you are in a car- threat usually coming from your left- strong side holster leaves you WHACKING the steering wheel. I use in IWB for a Mdl 36, usually worn weak side, butt forward. Have a minimal skeleton holster that I can carry most guns on belt, strong side, weak side, SOB (do not reccomend that), and it carries my Para C-7 quite well.
Best investment? A GOOD belt.