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ANSWERS: 2
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I dont know exactly, but I would guess its a comparison to the immigrants arriving at Ellis Island, who were not dressed very well, many were very poor, and looked it.
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It usually means people that just got to American from possibly an Asian country and they haven't assimilated into 'our' way of dress and behavior yet. It's when you dress like you don't know the styles or the labels and such.
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