Quoted:
Does anyone know of a good ankle holster I can wear with 8 inch high boots?
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I wore an ankle holster for the issue S&W snubby model 15 on my 8" flight boot for over a decade, flying all over the world.
Admittedly, the USAF flightsuit is generous around the ankle, especially if you leave the lower leg zipper undone, so it's easy to conceal.
I had a cheap nylon holster that had a velcro strap that went around your calf. I had to shorten it by stitching a fold into the strap between the calf strap and the holster. It attached with velcro around the outside of my boot. To eliminate the wobble the weight of the gun caused I wore the gun on the front of my leg, directly over my foot.
If you're going to be sitting a lot, an ankle holster is OK, but if not there are better options.