I carry a 27 in one, have for a couple of years. I don't think there's any chance there's enough holster/velcro to reach around a high calf, and I don't have Lou Ferrigno legs either
I also carry a Glock 27 in one. I purchased the calf strap afterwards because I felt that the holster itself would start slipping down my ankle. It does feel like the grip of the 27 wants to protrude out a little. Might just be my imagination because no one has even asked what the bulge is around my ankle.