I have a similar story. I got weird looks for wearing a respirator to grocery shop in early March (but felt totally vindicated by some idiot coughing furiously in the middle of the store). More recently I had a hassle getting into a hospital to visit, due to said respirator being a "street mask". Luckily one of the more enlightened staff focused specifically on the concern of it having a vent, we were able to have a reasonable conversation where I explained and demonstrated how I fixed that, and then she remembered me after that.

That same staff member lamented that her sister had gotten her some N95 masks, but she was prohibited from wearing them. I can imagine if Covid continues much longer (as it will until we find a magic vaccine, as there is no societal will to contain it), enforcement of the rules will become even more mechanical and unforgiving. Glaringly suboptimal outcomes imposed by top-down structure is a tyranny anarchists take issue with. Although the group behavior around Covid shows why the ideal is ultimately impractical for everyone, I still consider myself a libertarian.

I just had the second one.

Nobody would frown on me for wearing a mask where I live, even before covid.