I would choose pocket carry over ankle carry any time. Way faster to get to. I feel that if I am in a situation that I need to have my gun out. It needs to be quiclky acessable. I can also have my hand in my pocket on my gun without looking like a threat if I am walking across a parking lot of the burger joint, or grocery store.
If it were a concearn of dress. I would pick a Ruger LCP. Small, slim, and not too heavy. It is smaller than a pack of cigarettes in a pocket holster. They make a holster for it that makes it look like a wallet.
No matter how many times you do it and nothing happens it only takes something going wrong one time to kill you.