Well, I am genuinely sorry for writing like everyone would know my pet favourite headcanon which coincidentally is also about wardrobe choices in 9×09. I typed out a massive post once and gave up because I was tired and grouchy and then I guess never went back to it but continued projecting an aura like everyone knew it now. 😛
(disclaimer that this is literally just an amusing headcanon of mine, and while I love it and will defend it to the death, I don’t think this was intentional, rather an oversight on continuity from whoever is in charge of dressing them like walking Ken dolls between scenes)
Basically, they unexpectedly bump into Cas at that crime scene with zero warning they’re going to see him and Dean’s hair is all flat and soft and bed-head and asking you to run your fingers slowly through it and… *blinks*
By the time they get to the bar in the evening none of them have changed into more casual clothes or anything, and given there’s a pretty regular standard set on the show of Sam and Dean changing out of their suits at the first available opportunity, they probably didn’t stop by a motel or anything or they’d have definitely changed, so it’s reasonable to assume they’ve not stopped anywhere comfortable long enough to do anything about their more obvious wardrobe choices.
Anyway at the bar Dean has a ton of product in his hair and it’s combed alarmingly upwards.
Since there’s only one factor different between these two scenes aside from the hair and that is Cas’s presence, I like to think of Dean seeing Cas unexpectedly at the crime scene, freaking out about his lazy style that morning where he didn’t bother with his appearance because it was just him and Sam on some boring case where they wouldn’t see anyone important.
Hence the hilarious mental image of him panicking and diving into some grimy bathroom somewhere along the way with a comb and hair gel and frantically trying to make himself look presentable, explaining the change in hair between scenes.
(grabbed the screenshots from Home of the Nutty because I don’t own season 9 on DVD yet)
I also find it amusing that, at some point, he retied his tie, because the stripes aren’t aligned on the knot in the same way. This wouldn’t be accounted for by him simply loosening the knot (if anyone doesn’t know how a tie loosens, the knot remains in place but slides down the “tail” portion of the tie). The group of stripes in the first photo is over toward the right-hand side of the knot, and in the second photo is all the way over at the left. Which means Dean probably removed his tie while he was working on his hair. And he didn’t just loosen it and slip it over his head, as if he intended to put it back on. Nope.
I like to think he considered leaving it off altogether, but then panicked and thought it might look like he was trying too hard to be casual, especially since he already changed up his whole hairdo. It makes me happy to picture him standing in some grungy gas station bathroom having an existential crisis over how many buttons to undo and whether to leave the jacket off and roll up his sleeves, or whatever. Especially after he’d already shared his whole “how to dress for a date handbook” with Cas in 9.06.
Dean, staring at himself in the mirror: “I’m probably safe to undo the top button, yeah, because Cas thinks undoing more than that means it’s a date now… but what does he know about ties? Probably nothing. Then again, looks like he finally learned how to tie one properly… oh god, does that mean someone’s been teaching him about fashion? If so, WHAT CAN I REASONABLY GET AWAY WITH HERE WITHOUT BEING OBVIOUS?!” cue dean’s panic attack now.
OMG YOU MADE IT EVEN BETTER.
This probably explain’s Sam face in the bar scene too. He knows Dean took a stop somewhere and came back suspiciously spruced up yet anxious.
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