There seem to be two separate concerns:
I can't wear this hat because it would show pride in some country unrelated to me, which makes me sad.
Hats are all about having fun decorating your avatar. They aren't about showing pride in whatever is depicted in the decoration. We have hats strongly associated with Mexico, Scotland, Russia, Japan, and Brazil. We have "hats" inspired by Star Trek, Apple and Android themed hats, hats referencing dark comedies, a headband from an anime I've never watched, holiday ornaments of various types, a pair of animals, and two food items you can pretend to eat or wear.
The point is, if the hat doesn't fit your interest or temperament, if it doesn't amuse you to place it on your avatar, pick something else. (This, by the way, is the advice that folks on Mi Yodeya gave about wearing the Saint Lucia wreath.) Each year there are 30+ hats to be earned and worn. Part of the reason we have so many is to maximize the odds you'll be entertained.
It seems to me that the hat for posting a question through the mobile apps could easily have been made to appeal to a wide audience.
We give our designer a great deal of latitude when it comes to design details. For instance, my description of "On the Road" was "a trucker hat". I had a vague idea that it would come out looking something like:
But I didn't put any particular thought about what would be printed on the hat. (In sharp contrast, I specified exactly what should be on the "Handegg" helmet.) Nor did I expect that the hat would come with a CB handset (which was a perfect touch). So when I saw the result, just about the only thing I thought was "yep, that's a trucker hat". I suppose I ought to have also thought, "could we put something else on the front panel?" But the fact is, I didn't.
However, that brings up a problem: what should the cap have on it? I honestly can't answer that question because the current design perfectly stereotypes the American truck driver who (presumably) is forced to use his or her mobile device to ask a question. Obviously, it's not just Americans who love trucks, but when I think "trucker" I do think of the sort of people who would own and wear a hat with USA silkscreened on it.