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Why Dean’s Heaven Outfit is so Cursed

You may have seen my previous post about why Dean’s outfit in heaven is so cursed, but since then I have spotted even more.

According to Jared at the Virtual Con after 15x20 aired when asked ‘Were any lines added or ad libbed by you two [Jared and Jensen]?’ (starts at 29:28 timestamp)

… So, when we’re on that bridge and uh, and Dean says, “Heya Sammy” and then it cuts to Sam, and I’m dressed like, as best I could, like uh like the pilot with Dean, y’know. …

So from this, we know that Sam on the bridge in 15x20 was supposed to be dressed like the pilot. I infer that Dean was also supposed to be dressed like the pilot but based on the wording it’s possible that’s not what he meant. As soon as we got BTS pics from the last day on set however, we all pointed out that they were dressed like the pilot but there is a difference.

So what did Dean wear in the pilot? He had on 2 different outfits. First a dark jacket and a red shirt.

After Dean gets covered in mud, he changes into a denim shirt and John’s leather jacket.

Another thing to note is that both Sam and Dean wear sneakers in the pilot. No boots for Dean.

So it looks like for Dean in 15x20, the heaven outfit is based on outfit 1 with the dark jacket, plain red shirt and jeans.

Dean consistently has plain red shirts through the seasons and continues to wear the dark jacket until 9x03 so I would bet that the very jacket was sitting in storage until s15.

Something to note is that while Sam is in a virtually identical outfit in 15x20 and the pilot, Dean is not. They must have had to source Sam’s outfit specifically for this. Sam does wear a hoodie and a beige jacket in later seasons so they could have built it out of Sam’s wardrobe but they chose not to. He does not wear these exact clothes at any other point in the series apart from in Heaven. Dean’s Heaven outfit is just made out of his clothing from later in the series. They both wore sneakers in the pilot but in Heaven Dean still has his boots while Sam is wearing sneakers.

Compare:

If I was building Dean’s heaven outfit out of later seasons outfits, I would have chosen his plain red shirt (note: this is not the Demon!Dean/MoC!Dean shirt, it is a different one).

By the later seasons, Dean doesn’t actually wear dark dark jackets much. His only black jacket in s15 was this denim one which he has had since 10x04:

But the wardrobe department decided not to go for these and instead decided on cursed items instead.

So what was Dean wearing in Heaven?

The Shirt

Now this shirt is just plain cursed. This is only seen at 2 other points in the whole series, and it was a new one for s15.

We first see it in 15x04 Atomic Monsters for the Chuck AU where Lucifer!Sam kills Dean. Directed by Mr Jensen Ackles himself.

Thanks to him, we also get a good look at the shirt

So this is the first time we ever see this shirt and its for a Chuck AU where Sam kills Dean.

The second time we see it, its in 15x13 and this is another cursed appearance. It is worn by Huntercorp!Dean while pretending to be our Dean in the bunker.

And why was Huntercorp!Dean there at all? Because Chuck was destroying worlds.

When AU!Dean leaves the bunker, there is an exchange that is a bit cursed.

Huntercorp!DEAN: Oh, uh, you think we could keep the flannel shirts?

DEAN: No.

So the shirt actually gets a mention by Huntercorp!Dean.

What we see here is that this shirt is NEVER worn by our Dean. It is worn by a Chuck AU Dean and Huntercorp!Dean fleeing a world Chuck had destroyed while pretending to be our Dean.

We never see our Dean wear this shit until Heaven which seems like an odd choice.

Dean also doesn’t normally wear red and black plaid shirt. In fact, the previous one he had has an interesting history as pointed out by @wigglebox when we were discussing it.

It is first seen in 12x21 and he continues to wear it into 12x23 when Dean has to go into Mary’s mind.

We then see it again and for the last time in 13x16 Scoobynatural.

Both of these episodes are sort of AU episodes where he’s venturing into another character’s mind or heading into Scooby-Doo world.

So both Dean’s black and red plaid shirts have a cursed history relating things not being real and for this specific shirt, AUs. They could have chosen a plain red shirt almost identical to the pilot but they chose not to.

The Jacket

Dean has this jacket for a long time. He has a blue one and a black one. This black jacket has been around since s9 and gets worn a fair bit. On the whole, it doesn’t have a very happy history, its first worn for Kevin’s funeral in 9x10 and is worn after Claire is bitten by a Werewolf in 12x16.

However, the most notable thing about this jacket is what should have been it’s demise.

Dean is wearing it in 13x23 when he fights Lucifer and AU!Michael takes over his body.

At the end of the episode, we see that Michael has changed dean’s clothes and presumably ditched them somewhere.

Dean comes back at the end of 14x02 wearing Michael’s clothes. He arrives back at the bunker in 14x03 and changes into Dean clothes but is missing his watch for the whole episode, presumably because Michael ditched it. The denim shirt Dean wears in 13x23 is never seen again (yes, I have watched s14 and s15 just to check and have spreadsheets for Dean’s outfits!). His boots are back in 14x03 but I suppose you could argue he had multiple pairs.

We are left to assume that the jacket is also gone (and it really should be gone) but it makes a miraculous reappearance in 14x13 Lebanon.

Now this episode is an odd episode. They get their Dad back by messing up time, Cas doesn’t know them until they reset it back again. The shirt in this episode is also notable and I will write a post on it soon. So again, we have part of Dean’s heaven outfit connecting to alternative timelines where it really shouldn’t be at all.

BUT IT GETS WORSE EVERYONE!

This jacket appears at just one other point in s15. Now if you had to pick the most cursed of cursed times to put it where would you put it on Dean?

The Vamp Chuck future in 15x09 where Sam and Dean die as vampires.

So this jacket should have disappeared in 13x23 but reappears for an episode where time is altered in 14x13 and when Chuck is showing Sam the future in 15x09 if they ‘win’ and they die as vampires. Dean is then killed on a vampire hunt in 15x20 and ends up wearing this jacket in Heaven. Cool, cool.

This jacket becomes connected to our Dean but in altered timelines and worlds while the shirt is connected to alternative Deans. Both the shirt and the jacket have direct connections to Chuck.

So we seen Dean in Heaven wearing this cursed outfit drinking cursed El Sol beer with the same cursed monkey from 14x13 Lebanon (see above, it was in the roadhouse too).

This is not an outfit that screams happy. This is not an outfit that screams Sam and Dean won. This is an outfit that seems to scream Chuck won.

I guess we’ll just have to wait until Jackles manages to get a continuation…

One final odd thing to note. We all remember Jensen’s video posted before the finale when he was dressing up as Dean for the last time “at least for now”. Well he wasn’t actually wearing the outfit Dean wore in Heaven although all the Heaven scenes were shot on the last day of filming, the 10th of September.

He was wearing the Heaven plaid shirt, but not the Heaven Jacket. It was Dean’s black denim jacket I pointed out earlier. If you look it has seams that the Heaven Jacket doesn’t and the pocket flaps are a different shape.

I have gone through all the Heaven scenes and he is wearing the Heaven jacket in all of them. But I can’t think of a reason why on a hot day in September when Jensen is getting changed into costume he would have a different one of Dean’s jackets on over the shirt he needs to wear for the scenes.

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