I routinely carry my S&W Model 60 in a Galco Ankle-lite holster inside my Tony Lama boots. However, most of my boots have a wide "top" (technically called the "shaft"). Very comfortable with the wide "top" boots. I tried to ankle carry with regular shoes and the S&W tended to slip down my ankle to below the cuff of my jeans. Not good with shoes, but I wear boots 99% of the time, anyway.