The reality is, as the show and Dean himself have made explicit at various times during its run, that John Winchester forced Dean to be a surrogate mother/spouse/feminized (in his view) caretaker role while simultaneously forcing him into as many hypermasculine tropes as he could think of and rewarding him only for being as much like him as possible. This would do a serious number on anyone’s head and I think the writers and the actor who plays Dean all realize this. Watching Dean face and resolve that harmful, abusive dichotomy over the years has been a unique experience for me as a viewer. The show has really benefited from having Jensen Ackles in the role, who has given him a level of nuance - and allowed the writers to plumb depths - that probably wouldn’t otherwise be there."
Dean looks at him, curious; tips his head to one side much like Castiel usually does. He’s considering him, as he has often these past few weeks. He looks him up and down. “Nah. More like… a tourist.” He flips through the racks of clothes in front of them one last time, then shrugs as if giving them up for lost. “C’mon. We’ll get you some ray bans. Maybe a Hawaiian shirt.”
But they go for neither of these items, and instead Castiel finds himself awash in a deluge of fabrics and colours, hands tripping over the rails of things so pretty he could almost eat them; the world a swirl of colours, of shapes, and of Dean, its muddy-coloured accent, mocking in bluejeans and his old, battered leather jacket. He’s a leather-strip bracelet, something old and sentimental, nothing like the things he wants Castiel to choose – but Castiel has been old, has been used, and has been useful.
Privately, he thinks, he is somewhat ready to be treated as new.