Skunk,
I'll often change clothes twice a day from casual to exercise and back. So I use a carry method that's independent of what I wear. Even works with only my underwear.
I wear a separate, dedicated belt for holster and whatever. - a 1 3/4" belt with a flat buckle from Brigade Quartermaster. It's not a thick stiff belt from a major holster maker but it is a heavy duty nylon strap and buckle.
Worn over my underwear and under my pants, shorts, slacks, suit, whatever, it disappears. Since the holster is on it and not on an external belt, a lot of concealment and retainment issues are eliminated. Weapon stays in position regardless of what my pants are doing.
At the moment, I've got a Glock 19 in a Fist #K1 IWB. Usually I've got a snubby instead (also a Fist #K1) and often a Seecamp in an Aker pocket holster in the right front pocket.
Although I can carry a knife on that belt, I normally carry a CRKT M-16SF in my waistband (not pocket) at 3:00. Fox pepper spray is in left front pocket with money clip. Choate executive ice scraper is in right rear.
Regardless, the key item is a separate belt under my clothes. Doesn't need special clips or doo-dads to be tuckable. A variety of holsters become concealable. Can even be used like a smartcarry if desired.
Larry