I haven't read the entire thing but I just would make sure he's not wearing it at any airport. That's not something you want to mess around with joking or not.
If he has short, dark hair, and I glanced at him quickly, I would probably think it was my youngest daughter. She is 16, a Junior in HS, and is about the same size as your son. She also has an old Security shirt that her older sister gave her.
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