Here is what I have carried:
Glock 30
11+1: smooth, accurate and reliable. A bit heavy. More winter and fall carry.
Glock 27
9+1: easily concealed, lightweight and easy to draw.
Ruger LCR
Pocket carry 38+P. a bit thick for pocket carry. Sometimes I went IWB but it was no advantage to a G27.
Ed Brown Special Forces, 4.25"
IWB: similar weight to a G30. I'm far more accurate with it. More winter and fall carry.
Sig P238 and P938
Pocket carry for the 380 and IWB for the 9mm. The 9mm trigger is not smooth. The 380 is very easy to shoot. Pocket carry in a wallet holster. Easy to draw either. Formal outings. Cannot drink though.
S&W 442
Easily my favorite pocket carry gun. Accurate. Handles recoil well. Walk in the parking lot with my hand in the pocket and it's ready to draw.
S&W 586 L-Comp 3" magnaported from the Performance Center
IWB in a remora holster. 7 rounds of 357 125 grains. Exceedingly accurate. A bit heavy, especially in the summer.