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Has anyone done a sort of...tortured prisoner look before? I don't know the best way to approach making the costume.

I did a reference sketch but I'm not 100% set on it:


My original plan was to buy the material, get some shirt/pants patterns and make it myself, but I found this costume: Men's Convict Costume - Mens Prisoner Costumes
It might be easier to buy that, rip it to pieces and throw blood/brown colors all over. I kind of wanted it to be loose anyway, so a men's size might...look cool?
The ball and chain is a maybe; I don't want to be tripping everywhere I go. Or have my friends trip on me.
Although that would be funny.

My skin will look torn wherever the chains are and I'll have stitches all over my stomach, head and arms from experiments.
Um...I was thinking about striped stockings for my legs, but that might be a bit overboard so I'm leaning more towards black stockings with a bunch of rips and tears.

Any input is much appreciated <3
 

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You could do a leg cuff with a single damaged link hanging off it to get the effect without the trip hazard. Alternately damaged skin around the ankle with chains and damaged skin on the wrist would get the point across that you got out of a leg binding and eliminate the trip hazard. If you are using plastic chain around your wrists and neck, a bit of metal dangling from your ankle would give a nice sound effect to help create the illusion the rest of the chains are metal.

Something like this:
 
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