Once upon a time, I regularly wore on my ankle. It does take some getting used to, although you may find that normal taper-cut jeans will be more likely to print and slow your draw.
As a right-handed person, I tended to keep mine on the outside right ankle, although on occasion and dress, I might switch to inside left. Personal preference, and what you train with. I've heard arguments both ways, and used both, depending on circumstances.
I found that after a couple of weeks, it became second nature and I was less self-conscious about it. Best worn with slacks, khakis, or boot-cut jeans, in that order.
To disparaging posters - no, you won't fit your hand-cannon in there, but I was always discretely armed. Always. You cannot always carry a full-size, and better armed with anything than nothing.
[Edit] About the holster - I recommend heavy padding. Mine was a thumbbreak leather holster, heavily(!) lined with fleece. Very comfy.
