Eyeless Jack outfit headcanons
The first one would be his casual, the sort of thing he wears indoors when doing whatever. I feel like he'd definitely be a comfort over fashion type of man, but would love an ocassional band t-shirt or hoodie.
Due to the tar pouring out of his eye sockets, he would prefer to wear all black so that it isn't as noticable and would prefer shirts with designs on the back instead of the front, so as to not risk them getting ruined.
This is also the reason he would have exclusively black bedsheets. The tar is impossible to wash out.
I headcannon he would gravitate towards looser, baggier clothing made to last and enjoy wearing things that feel heavy and sturdy. In any case, it would always be quality over appearance for him.
The second outfit would be his work uniform, almost. A very simple outfit in which he can sneak easier, with all his necessities in a bag attached to his thigh. This would make his stuff easy to reach without the clutter and noise of a larger bag. It's simple, covers everything on him that looks inhuman and functions in a way he needs it to.
The third outfit is a cold weather iteration of his work outfit with a larger bag. He would rarely use a bag like this, but if the situation ever called for it he'd go for something over the shoulder, where he can still easily reach into it. He would detest backpacks because he'd have to take them off to use them and would constantly worry if they'll snag on something while he's moving about. The bag also has a belt attaced around his waist in hopes of making it move less.
As for the jacket, I feel like he'd have a loose leather jacket under which he can be in whatever sweater he wants at the moment, especially because of he'd prefer layering under it. I also hc that he runs pretty warm and doesn't feel bothered by the cold for the most part, so he can go through a harsh winter only in that jacket. The jacket is also the type that has a double zipper situation and is unzipped at the bottom so that he can crouch easier, without the jacket restricting his movement in any way.
He would never use scarves or anything decorative that could get tugged easily. His hair would always be in a bun while working as well, tucked away in a hood and unreachable.
Under the baggy jeans he wears boots or sneakers, whatever fits the terrain he's dealing with better.
In order to not risk being found out for being inhuman, especially if someone manages to take a photo of him, he covers his skin totally. He always wears long sleeves and gloves.
But another thing he would do is roll up a very high turtleneck completely, covering the lower part of his face. He puts his mask on after doing so, this way the skin isn't visible on his neck either.
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