I don't tell anyone how to carry their personal defense tools so all I'll note here is that, yes, an ankle holster takes getting used to and, also, it's probably IMHO the worse possible way to carry a concealed handgun. I think it's real utility is for uniformed officers and their backup guns, or maybe undercover personnel, but not as a primary concealment device for an average citizen carrying a handgun concealed, be it a tiny Ruger LCR, a J-frame, or any such small handgun. You're a member of the fraternity of blue bloods so I imagine you actually know all this but I feel obligated to say it, anyway, even if just for the non-LEOs out there.
Just my two cents.