Responses
I don't know. You do you. I may look young for my age but at twenty-seven, I was not going to look like a Catholic school girl in a uniform. I could pass for US TV public high school but not IRL high school.
From my mid twenties to now my mid thirties, it would look like I'm trying to hard to live in the past. I realize he wants to recapture that moment lost to him but the clothing just doesn't suit them anymore. A couples outfit would have accomplished the same thing, since they could pretend that they were in high school going on a date during break or something.

School uniforms at twenty-seven at an amusement park? I would have died.
Now the cat ears, I can get behind. It fits in with the setting. Your couple shirts would have been perfect.