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I carry a Glock 22 (sometimes a 23) IWB when I know I'm gonna be reaching, bending, lifting, etc. My IWB holsters are a CTAC and a Pro Undercover (both made by CompTac).

I carry at ~3:30 either way.

Since I got the Pro Undercover, the CTAC is reserved strictly for tuckable duty.

The rest of the time I carry OWB in a Tucker HF1. The Tucker actually conceals better than the IWB rigs, unless I'm engaged in the above mentioned activities.

A quality gunbelt is essential.

The biggest problem with concealing IWB, for me, happens when I sit down.

With OWB, the pistol stays tight against me.

With IWB, my pants tend to pry against my belt and pull the grip away from me a bit. I have to pay too much attention to what my cover garment is doing behind my hip to be sure the grip isn't printing through when I'm sitting where I can be seen from behind.