One of the problems with "masks should be required" is that it lacks nuance. Around where I live--exurbs of a major NE US city--they're required and pretty much universally used in stores as far as I can see. However, outside, it's very mixed and personally it seems pretty reasonable. But I'm sure to some people it seems as if people aren't being reasonable.

Certainly I'm not wearing by myself in the woods. But perhaps that's seen poor practice by some. No idea what things look like in the city. Perhaps I'd find it uncomfortable.

Most of the mask orders I've seen take that into account though, requiring masks indoors and in outdoor spaces where social distancing is not possible or enforced.

It is. Although some people seem to feel strongly that's not enough.

The lack of nuance is a feature and not a bug. It takes the decision out of the individual's hands since people can have any number of reasons ranging from valid to incomprehensible for why their specific activity doesn't require a mask. We have already tried leaving it up to individuals for the last 4+ months and that clearly hasn't worked. The choices going forward appear to either be to put stronger precautions in place until there is a vaccine or continue to let tens or hundreds of thousands of more people die unnecessarily so we can be slightly more comfortable while outside our homes.

Well, where I live which is about as blue as it gets in the US, people are being good at wearing masks inside based on what I've seen--essentially universal. And they may have masks for walking around in close contact outside but they're not required or generally worn when people are, for example, sitting down and eating outside or walking separated by some distance.

My understanding is that is pretty much the situation even for places where that are relatively enforcing masking in the US.

Strongly agree.

Public health policy and individualised medicine are, or at least can be, vastly different things.

If you tell everyone they must wear a mast at all times, some people still will not.

If you tell everyone a more complex set of rules than masks at all times when out of your usual place of residence then people will fabricate all types of fictions that exempt themselves from the rues.

I generally agree, and I personally don't wear a mask outside when I walk in my neighborhood for this exact reason (very low density, plenty of space).

With that said, it appears that if there is any gray area in the rules then the general population is almost sure to abuse them. In this case, I think it's better to err on the side of caution and make it 100% mandatory so there is absolutely no gray area.

I mentioned this in another comment already, but this is what’s being done in New Mexico.

The mask order was extended to, basically, “wear a mask if you’re outside your house”. This includes exercising outside. Personally, I find that part a bit excessive; however, my understanding is that it’s meant to counter exactly what you pointed out: as long as there are any exceptions, some people will reason their way out of compliance. A 100% mandate is just easier and simpler to follow.

I now wear a mask when walking in my neighborhood after I noticed other people wearing masks too. Chalk it up to peer pressure I guess, but to me it’s a very small price to pay if it helps enforce mask-wearing in other contexts.