My new cordovan boots are hurting me at the top of my ankle (both feet). At the end of the day I even have small skin cuts at this level and I have to wait few days that it heals before being able to wear them again.
Just to be sure, will it get better after several wears? Because right now it is really painful.
I had a similar issue with a pair of CXL PCT boots, but a bit lower actually.
Once the boot broke in and conformed to my geometry, I had no further issues.
I'm going through a similar break in with a pair of LHS at the moment...