juliawise 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.