I recently saw an episode of Leave It to Beaver that I think has the "Society Marches On" trope, though I'm not entirely sure. But there's an episode where Beaver and his friends buy shirts with either a monster or a martian, with eyes popped out. Really ugly designs. Beaver and his friends pledge an oath to wear their shirts to school together, only their parents won't let them, and only Beaver is successful in being sneaky enough. When he comes to class, all of the kids instantly laugh at it, and the teacher is mad that he's disrupted class with his shirt.
I don't think a shirt like that would be a big deal in this day and age, but it makes me wonder if school dress codes were stricter back then. I think that's the only time on the show when anybody in the class wore a shirt with a character on it. When I was in school, it was common for us to wear shirts with funny illustrations on them, and we usually didn't laugh at the sight of the shirts.