Quite reactionary, I know, but after I got covid this week I found myself wondering if I could've dodged it by wearing a mask, at the very least on the plane. However every mask I've ever worn is unacceptably uncomfortable; Either my ears hurt after ~half an hour or my glasses fog up (meaning the mask isn't even sealed properly??) and usually both. The least worst mask I've used was one that had two straps that tied all the way around my head, and there was definitely no good seal on that.
1000 mana bounty to the first person that convinces me to buy a mask and after trying it, it is comfortable to use for 10+ hours. (if for example I need to replace the mask every 4 hours that's fine, so long as I can be wearing a mask for 10+ hours with little interruption.)
Whereas kn95 masks use ear loops, regular n95 masks have 2 straps that go all the way around the head. I have found them to be much more comfortable because for me the pressure around my ear is the weakest link. It also seals much better than a kn95.
I bought this Harley brand on my own when my hospital is not supplying n95 masks and continue to use it even though my hospital now supplies them because I find them much more comfortable than any other mask. I use them for 12 hour shifts, which realistically sometimes means 14 hours a day.
I am now anti-mask. If masks were like watches and you could wear one and begin to not even notice it after a day or two, then it would be perfectly reasonable to require everyone to wear one for health and safety. But every mask I've ever worn (not an exaggeration) has been unacceptably uncomfortable.
Sounds like you might want something a little more durable than the typical mask. I have several friends who work in medicine (and had to wear masks all day during COVID waves) who like this one. There is a more involved head strap so it doesn't hurt the ears. There is also a soft plastic/gel seal around the face so it shouldn't fog up your glasses or dig into your face as much
I don't know how good of a seal you're looking for, but these are better than surgical and extremely comfortable; little pressure and lots of space for your face. They do fog up glasses in the cold unless you have them on just right though. The ear loops are a little big for me and I just twist them. https://www.amazon.com/gp/aw/d/B08MDRR7JJ?ref=ppx_pt2_mob_b_prod_image
I believe @d6e had a good Japanese mask recommendation.
(Planes are relatively safe btw; I doubt you caught it there.)
In many contexts, I use this.
Advantages: durable, so I don't have to keep getting new ones (you do have to replace the filters but not even that often); straps around back of head rather than behind ears and therefore doesn't make my ears hurt; good fit / seal (does not make my glasses fog); presumably provides better protection than a KN95.
Disadvantages: muffles my voice, making conversation difficult; takes up more space when not worn than a KN95; does get uncomfortable after about 4 hours (but anything would, and I almost never need to wear it that long anyway),
I use these: https://www.amazon.com/gp/product/B08Q8HKCTW/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1
They're KN95 - the Amazon link has all the info. I like them because they're the most comfortable high-quality (at least 94-95% filtration) mask I've found. Also, they don't smell bad when you put them on (or at least they smell much less than some of the other types I've tried). Plus I like the different color options!
They are disposable (which can be either a pro or a con, depending on your preferences/priorities). The nose seal isn't perfect, but you can make it fit pretty well; the other sides are all good seals. As an example, I always adjust the nose strap thing, and I've definitely noticed that sometimes when I breathe hard, the mask moves in/out, showing the air is clearly flowing through it. I don't wear glasses, but I can confirm that these don't hurt my ears almost ever (they do occasionally hurt, but that's usually a one-off and will be back to normal the next day, which is much better than most other mask types for me). I know some people don't like the masks that extend out, but I find it a lot more comfortable and breathable because it's less like your face is covered with this fabric that's pressing against you (while we're on it, they also don't leave impressions on your face). However, I hate those masks with two straps that go all the way around my head, so likely we have different mask ideals...
I used mainly surgical masks for most of 2021 iirc, and then at some point I switched to higher-filtration masks; after I discovered these, I've been using them pretty much exclusively (whenever I need a mask). I also got my friend to switch to them! (She was previously using masks that didn't fit her, while these work a lot better for both of us.)
Hope this helps! Good luck finding a mask that doesn't hurt :)

