You are WAAAAAAY Late on that kiddo. I'm a avid Medic myself so I've seen MtM not half an hour after the release.
Also, the comment was made long before the short was created (like just over a year ago) so the assumption of Medic's behavior at the time was purely up to the fans how they view him which Valve has done a good job at still honoring that in making the character neutral enough for the fans to let their imagination run and not become disappointed at a 'set in stone' single personality.
Lol, I can see riding boots having that problem. Actually, I bet that's why the medic in this pic hasn't thrown off his boots too
I was so happy to find medic-like boots with subtle zips up the middle of the calfs (I couldn't resist, and I partially blame your outfit's awesome - I'm slowly making my own). Comfy, correct design, and easily removed