I carried a Walther and a chiefs special in ankle holsters for over 20 years. It was the only way I could remain armed while running my business and dealing with hundreds of clients all day. You get used to anything if you decide on doing it that way.
The way I did it was to wear a boot, but a low boot, the butt of the gun sat on the edge or rim of the boot thus still making it quick and easy to get the gun out, but giving me better stability. "Only one gun at a time on the ankle, depending on what I was carrying".
With low shoes, the gun would pop out when you sat down. The boot would prevent that and also make it almost impossible to see with black or brown boots and a rubber grip on your gun.
My area was often hit by robbers back in the 70-80's when we only took cash, and were the first to start taking plastic. Now it really isn't that big a concern. Restaurants, hair salons, health clubs, back then had piles of cash laying around. Now, maybe 10 % pay in cash, if that. A good pub could easily have 20-30 grand laying around over a busy weekend. Many paid the help in cash also, so the night deposit was not nearly as large as the days take, most cash businesses would take the cash as "their money" and checks and CC's, got deposited along with enough to pay bills.
Even with full sized Larry Mayhems I could get a snubby or a walther in there, by wearing the holster up high.