The leather jacket once belonged to John Winchester. After John disappeared, he left the leather jacket in his motel room. Dean took a shower and picked it up from a pile of clothing. He then went to pick up Sam from Stanford. Dean wore this jacket for about five years, and was important to him as much as his amulet was. Dean never showed signs of wanting to discard it, but one year after the Apocalypse was stopped, Dean no longer wore the jacket. In 1997, Dean briefly wore this jacket while attending Truman High.