Comfortable carry conceal?

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I've gone through the same thing. I have been carrying in a pancake holster with an untucked shirt and its been very comfortable...that's for my M&P. I carry my KelTec PF9 IWB and forget its there.
 
Well, as you are aware, recoil and weight are inversely proportional. Thus no small "pocket gun" that packs enough punch will be "fun" to shoot. My PF9 is certainly my least favorite piece to shoot, but by god I can tuck it in my wallet and almost forget its there. Almost ;).

Now, my experience is that sub-compact guns do take more skill to shoot accurately then their compact, service, and full size brethren, because of weight and sight radius. Any sloppy trigger work or any shake, micro-flinch, etc. will instantly be revealed in a sub-compact, whereas a heavier gun because of its mass will conceal it from you.

If you are looking towards something more easy to shoot that still has bite, I second the suggestion that the Khar MK9 might be what you are looking for. It has an all-steel construction that will help with perceived recoil, and is still as small as the P9 for ease of pocket carry. It will, however, be noticeably heavier at first.

Thus, you need to ask yourself if the extra weight is a acceptable trade-off for extra confidence?
 
Comfort is extremely important. If the firearm rides poorly it can flash or print. A more subtle effect over time is that you may stop wearing it.

For deep conceal in an office environment, I prefer the old Seventrees style shoulder rig. KL Null sells them.
 
I still think the slimmer single stack guns are your best chance to "have your cake and eat it too"

Honestly, once you get used to having the weapon on your hip. Your not "comfortable" without it! A slim pistol like a P9 or PF9 would be very comfortable on the hip without much effort at all. I know some would say, "git yerself a 1911 or just forgit it" but in reality the weight of the weapon plays a big factor too.
 
Since you bend over too much at work to discreetly wear a pancake or standard IWB, may I recommend a quality "tuckable" IWB (and good belt).

I would NOT use an ankle holster. IMHO, you might as well not carry as use one for a primary weapon because they are too inaccessible. Don't take my word for it, though. Read this.
 
A good holster and gunbelt is key to comfortable concealed carry. Not an area to cheap out on IMO if you are going to carry every day.

If you go IWB, go with pants at least 2" bigger than what you normally wear. I was amazed at what a difference that made.
 
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