The issue came up when we discussed Hegel and nobody can answer it. There are papers about Hegel’s dress choices, but they are paywalled and i do not even know if they go into matters of headwear.
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The two primary relations of a hat are its practical use and its use as a signifier of social status or group. There is a contradiction here: a distinguished gentleman at a safari might want to showcase his status by wearing a fancy hat, but at the same time he wishes to protect his neck from the scorching sun. This contradiction is resolved by the most dialectical hat, a fedora with safari flaps.
the most dialectical hat, a fedora with safari flaps

Newsboy cap





