High level character wears gear intended for low levels

Jeans maybe, but the backpack and shoes are still autistic. If he's bringing important paperwork, he should have brought a cheap Manila folder. And converse? In the present day? As a grown adult? It's like he intentionally decided to dress up like a dork.

Ive never played a game that disallowed you from equipping your weaker gear based on your level
I doubt there are any