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OrphanWilde comments on Tell me what hat to buy - Less Wrong Discussion
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Experience-altering chemicals suggest -very- strongly to me that hats change your perspective and make you feel more sheltered and protected, as well as less personally involved in the situation at hand (reducing social emotions, such as empathy). I'd guess hats are worn by people who lack social skills as a kind of self-medication to help alleviate their anxiety, rather than because they don't understand normal people don't wear hats.
Traditionally, that's the role of dark sunglasses.
I am not sure you feelings about hats generalize well.
Both share the quality of decreasing the level of light entering your eyes (hats, by reducing your field of vision).
I was a huge fan of hats until I noticed the effect, which is limited to brimmed hats.
(Also consider social conventions about hats and their similarities to conventions about sunglasses. And consider the conventions themselves and how they would tie into these effects.)
Actually, no, that's not the important thing. Dark sunglasses hide your eyes, in particular their expression and direction. It's harder for other people to gauge you -- that's what provides the "sheltered and protected" feeling.
As to social conventions, I believe the ones about hats go back to showing trust (or submission) by making yourself vulnerable to attack.