This Dean Winchester screencap contains
pak, fedora, vilten hoed, homburg, cowboyhoed, trilby, fedora met vilten hoed, and stetson.
There might also be
vierdeukenhoed, campagne hoed, schipper, leghorn, panama, hoed, zeeman, skimmer, strooien hoed, livorno, panama hoed, matroos, stro hoed, jurk hoed, hoge hoed, opera hoed, zijde hoed, kachelpijp, topper, bever, silk hat, and beaver.
Sam died and Dean could bring him back. In a dream he learned that Sam change into demon and looks for a way to help Sam so he strikes a bargain with demon(Ruby) that he will go to hell and find Sam.