Dean: crumpled photo of family, recently taken photo of a woman he's never met, wallet holding a perfectly legal driver's license, car keys, cellphone with cracked screen, small flask. His clothes wouldn't be there because in his "real" life, he got into a severe car accident, and I imagine they would have been taken away/disposed of by his "real" family.

Gumshoe: cellphone with a dent running down the middle of the keypad, all of his normal detective clothes except The Coat, and a wallet so empty it could make you cry (they supposedly revoked his driver's license).