With a pocket holster, do you need to be careful about the pants you wear? I could see it being uncomfortable in jeans, but not so bad with Dockers or slacks.
I’m not up with the times and current fashions, but I think most jeans nowdays are cut like slacks. The only jeans I have that don’t work so good with pocket holsters is the old 80s style levies 501 button fly shrink to fit jeans. That style had small pockets and I woulnd’t put anything in those pockets but a set of keys...and even that is not easy to do since I can barely fit my hand into the front pockets even if they are hanging on a hanger instead of being worn.
Yes - with jeans, I prefer an inside-waistband (shirt tucked in) or external belt holster (shirt untucked). Depends on the weather and dress requirements.
Yes, not too comfortable w/ slim jeans.
I usually wear cargo pants, pretty full cut.
IWB works with shirt outside. The shirt should have a pattern, plaid, design, something to make any bulge more difficult to determine.