I believe costuming should be easy. Jack should be wearing a band/musician shirt, and jeans. Maybe he could wear a flannel because it somewhat screams "I AM A MUSICIAN!". Kind of. Here are some examples:
Basically, Jack should dress like an average teen boy (ignore that the examples are of adult men). Nothing too crazy, but something that shows he's a musician. If I'm being honest, he already dresses like that to school, so he won't really need a costume. But I'll still tell him to wear a band shirt and jeans/casual pants.
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