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Howl has an pretty interesting outfit. 
Is there like a specific background why he wears these kind of clothes?

I think it's just his uniform as Chief of Police, though maybe there's more to it, who knows ╮( ̄▽ ̄)╭

Well yeah, at first glance it looked like something out of the 1940's 

Fair enough! There could very well be something behind it, but I think it may just be an aesthetic choice that can be waived off due to the whole "parallel universe" thing. I'll be curious to see if it does have any deeper meaning/implication tho, cuz that could be interesting 😊👍