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Jack comments on A Rational Approach to Fashion - Less Wrong
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I never said there were people who didn't look good in a fedora. But it is a really good illustration of an accessory that people try to wear because some people make them work but fail again and again. There are certain people and certain contexts where it works-- but a beginner to fashion should not look and Bogart or Timberlake, see their hats and try to add the hats to their wardrobe.
Ditto cloaks, unless you already look like Glorfindel or similar.
Contrasting this with
How do we know what's too difficult for a beginner? Must we observe lots of people who strike a very good impression, and only seek items which are similar across the majority of the training set?
This may work, but not (I think) as well as looking for failure modes of an item you wish to adopt. Who looks bad in it? Who looks good in it? Can you find why? Which is more likely to be you?