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The issue is it has to fit the overall outfit. A fedora can still look really good if you have a well tailored suit to match it, while most of the things that look good with a cloak are, frankly, uncomfortable to wear everyday compared to modern clothing. This is why it's essentially only done for cosplay and larping nowadays, looking like that is fun every now and then but not so fun that you'd want to go about daily life dressed that way.