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I went through a couple or three holsters, but stopped with the Comp-Tac CTAC tuckable about three years ago (or is it four?). It is an IWB, and I wear it with everything -- winter, summer, khakis and polo shirt, suits, t-shirt, tucked or untucked, whatever.

I much prefer the IWB both for concealability and security -- it keeps the gun in tight. I buy pants big enough to go around the holster, and since I always wear it, I am not plagued with ill-fitting pants without the holster. I am also very much of the mind that sticking to one mode of carry is much more tactically sound --- I do not have to think in the least about where to reach for my gun. I have proven to myself that under sudden stress, having more than on possibility just results in confusion. So I CTAC all the time.