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Hmm maybe before she meets you she stumbled across some girls who where all dressed up and stuff? Since she has so little experience with the modern world maybe she assumed it was common and built her day to day wardrobe around it? That way we can easily explain why she was interested in it.
Hmm Chad as a caretaker type puts weird images in my head so a oc there would be best. For MHA hmm guess maybe Tenya is best since he's probably only one there I can see doing so.