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John's shirt is actually completely different from the boys shared shirt. His plaid is straight up and down, theirs has a separate shoulder panel that has the plaid forming an X. John's pockets also don't have the button-closed top flap. The pockets are just old school open.
16 things you didn't know-Supernatural: Eric Kripke's first version of the Supernatural pilot script ended with the Winchester brothers finding their Dad. He was dead on the ceiling! - The role of Ruby was written specifically for Kristen Bell. But she turned it down, so Katie Cassidy was cast instead.