I OWB carry at 4 O'Clock in a Lobo Pancake most of the time with Revolvers. I normally go to an Avenger style holster with my 1911, or XDm 40.
I have lots of Carry Shirts. I have 5 Woolrich Discrete Carry Shirts. I probably have another half dozen Fishing Shirts. I have a few others also. I just keep an eye open for shirts that can be worn with the tail out that fit loose enough for belt carry. Also I keep an eye on length.
Today I went to Church casual. Blue Jeans, Cowboy Boots, and a new short sleeve Rigg Shirt worn with the tail out. I was carrying a S&W 442 Pro Moon Clip with 2 spare Moon Clips of 38 +P infront of the holster carryed in a California Competition J Frame Moon Clip Carrier.
Tomorrow I will probably be carrying my 2-1/2" Model 66 snub with 2 shotshells up front for snakes. Then again I might carry my LCR-22 with 8 Stingers. Bagged a Copperhead with it over the weekend.
The more you carry the more comfortable you get. I had 17 years experiance concealed carrying as an LE before we got Concealed Carry here in Missouri.
I have a couple buddies who carry in the back pocket of their jeans. If the jeans do not fit tight a J Frame carrys fine in this manner.
One thing I do is swap my Billfold to my Left Front Pocket when I carry anything with a barrel over 2". In tight jeans I have also moved the billfold to a shirt pocket. Carrying at 4 O'Clock the barrel if over the top of the pocket with anything over a 2-1/2" barrel length. A 2-1/2" is border line getting my billfold out without showing leather. I have to be careful.
Work the bugs out as you go. After a while you will have a closet full of Jack Shirts, long Wind Breakers, long jackets, etc.
Bob