taw comments on A Rational Approach to Fashion - Less Wrong
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Companies that sell clothes would like you to believe otherwise, but for almost everyone the value you get going from "clean, comfortable, and well fitting" to much fancier levels is really negligible, and cost is pretty high. You are also quite likely to screw it up and hurt impression you make - people are bad judges of that as a rule, so it makes sense to go the safe way.