I regularly do because I wear a wear a cloth mask with ties over an N95 (sometimes with a face shield, too) when I go out. It takes a while to get all of that on and, because I'm slightly vain, I like my hair to look as neat as possible if I need to run an errand. Lyft drivers tell me they leave theirs on nearly all day to protect themselves and others because it's still not 100% known how long the droplets remain in the air.
I also wear my mask all the time when I'm out running or biking since I live in a pretty densely populated area with known cases of more virulent Covid strains. I'd much rather deal with the minor inconvenience and maybe overkill of wearing a mask when I leave the house than potentially being responsible for killing someone or contracting a virus we don't know much about and possibly dealing with long term side effects. If I lived in a rural area with a low population density and it took a while to get from my house to wherever I needed to go, I wouldn't wear a mask in the car.
Honestly, I'm much more likely to judge someone not wearing a mask in a store who potentially puts more susceptible people and themselves at risk of a deadly virus than I am of what people are doing in the relative privacy of their cars.