I define a pocket pistol as must fit in a shirt pocket.

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My Ruger LCP fits into the bellow-style shirt pockets on my 5.11 shirts. It even fits in a cuff pocket on one of their aramid "flash" shirts.
 
Glock 27 is the absolute max for pocket carry.

I define a pocket pistol as a pistol that fits in my front pants pocket without looking or feeling too awkward. In about 15 out of 20 of my pants, I can pocket carry my Glock 27 in my front right pocket. About 2 of my jeans are too tight with pockets too shallow. My Glock 27 doesn't disappear in any of my pants, except my cargo pants. It looks like a book or a Blackberry, which is quite common nowadays. I'll admit that my frame and my shape allow me to carry a substantial amount of things in my pockets without looking awkward.

I like pocket carry in my front right pocket because the gun can be half drawn without anyone knowing. That's not possible with waistband carry. On the other hand, drawing from a seated position is difficult with pocket carry in pants.

Off topic, carrying a Glock 27 in a Smart Carry holster is a cinch, and I use this method quite often.
 
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