As the younger brother of Dean Winchester (Jensen Ackles) in The CW's Supernatural, Sam (Jared Padalecki) has seen his fair share of demons, angels, and other creatures. In line with his role as a hunter and Man of Letters, he wears fairly utilitarian clothing like work boots and heavy denim. Up until it was removed by Castiel (Misha Collins), Sam had matching anti-possession tattoos with Dean.

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