I tried shoving my SP101 into the front pocket of my cargo pants yesterday using a Remora holster, just to see how it worked since the blasted holster didn't stay in my waistband. The gun actually hid quite well, although it was too heavy to be practical in a pocket.
I could easily see an LC9 or LCR in a pocket holster. One advantage would be that in a hold-up situation, you could reach for the gun when ordered to hand over your wallet and either draw it quickly (if the thief was distracted) or pop the holster off and fire it through the pocket.
I can see no practical purpose for an ankle holster unless you need to defeat a pat-down or something. Clumsy when running and impossible to draw quickly.
I carry AIWB for speed and to facilitate retention from snatches. When I'm wearing a trench coat I might carry in a pocket.
EDIT: Just realized I went off topic on a ramble. My answer to the question would be, cargo pants or carpenter jeans. Carry would be in the front pocket or, if the gun was small enough, the rear pocket using a "wallet" style holster. My daily wear is cargo pants, loose button-up shirt that's usually unbuttoned (t-shirt underneath, tucked into pants) and army surplus jacket.
Last edited by craZivn; April 22, 2013 at 09:25 PM.