Eh, I don't think that a middle aged woman wearing a character shirt is trying to chase her lost youth. I see plenty of women wearing t-shirts and sweatshirts with college logos or sports logos and those don't seem that different than a character shirt to me. I'll wear both kinds of shirts occasionally and I'm 47.
However, I think it's kind of pathetic looking when I see middle aged women chasing their youth by dressing like the
50-something woman who was wearing a mini skirt and thigh high boots with a low cut tank top with lots of cleavage showing. My 20 yo dd was home from college and told me, "Mom, thank you for dressing age appropriately."