Harry: you just always found this outfit looking cool and relaxed on him.
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Ron: you've just always loved Ron in sweaters, you just don't know why.
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Fred: you just always thought polka dots and nice suit jacket looked good on him.
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George: this outfit just is modern but still comfortable looking and you love it. Plus the shoes are super nice.
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Draco: it screams business casual and it gives Draco a respectful look but he's still comfortable.
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Neville: you just always thought this outfit is perfect for Neville. It's super nice looking and it's sophisticated.
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Marauder era James: it just always seemed like a style James could rock and he loves it too.
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Sirius: it shows that he has fashion bug it's also super comfy so he loves to wear as much as you love him wearing it.
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Remus: obviously a kinda biggish coat couldn't be worn all year... unless your Castiel... but when Remus wears it, it just looks like it brings out his cute nerdy personality just a little bit and you love it.
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