Pretty sure that this is everyone's favorite iteration of Dean Winchester. Demon Dean only lasted about two episodes but even in that amount of time there was a change in his style of dress that lasted throughout his darker Season 9 arc. Like Will Graham, Dean Winchester is mostly seen in jeans, flannel and hiking boots, reflecting his Midwestern roots. During the darker season however, his shirks all of the above for slimmer, black jeans, leather and darker toned t-shirts. Since he is very firmly not a demon for most of Season 9, this change in costume style seems more so to reflect his darker mood as he deal with the curse on the Mark of Cain. We have to say though, leather jackets definitely look good on this character.
Bobby: Let me get this right. The ice caps are melting, a movie where a girl goes all the way with a fish wins best picture, and that damn food idjit from The Apprentice is the President. Sam: Yeah. Bobby: And you call where we come from the apocalypse world? Sam: Good point.