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I too was on the search for the Holy Grail of holsters. I still haven't found it. But the closest I've come is the Comp-Tac C.T.A.C. I carry a Kimber Ultra Covert II in it almost daily. At work it's usually kakhis and polo or dress shirts, and at home it's jeans, denim shorts, or cargo shorts usually with a t-shirt or untucked polo shirt, sometimes a camp style or nice button up instead. It conceals well under all of these. My brother is a gun enthusiast and a cop. We have an ongoing game between us trying to figure out where the other is carrying and he couldn't find it until I showed him. The only time I can't carry the Kimber is when I'm wearing a white or really light colored dress shirt, and then, only because the color of the gun shows through the shirt. For those times I pocket carry a Kel-Tec P3AT. I've also been wearing Under Armour compression shirts every day. I started wearing them a couple of years ago on occasion when I started carrying IWB, then it got to where I didn't like carrying IWB without one. Now, I don't ever go without one. I'll attach a pic of the holster on, and one covered up with a polo for you to look at. Also, I can't stress the importance of a good belt enough. As a shameless plug, Comp-Tac currently has some clearance belts on their website. They're kydex reinforced. They're also seconds, but I'm not worried about a crooked stitch line or anything. I just ordered a new one myself. Hope that helps. Tons of other good advice on the thread here too. Good luck with the holster hunt.

Holster in place before tucking shirt in:

After tucking in shirt:


Edited to add: P.S. that's the Under Armour shirt, not my undies!