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in the early seasons of supernatural, sam wears unique clothing. he wears jeans with detailing on the pockets, his signature hoodie, and lots of graphic tees. even his computer has cute little stickers on it.
yet as the seasons go by, he loses more and more of his unique clothing until his wardrobe is nearly identical to deans. this loss of personal style tracks with his willpower and willingness to fight with dean and his assimilation into the hunting lifestyle.