atucker comments on A Rational Approach to Fashion - Less Wrong
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It's very rare to get feedback on fashion - I could probably count on two hands the number of times in my life that someone has said something about my clothing - so how do you improve?
I ask people who I trust will actually criticize me.
My sister pretty vocally and specifically hates particular things that I wear, and will say so when asked. My girlfriend is incentivized to try and make wear nicer clothes, and knows that if I'm asking her for fashion advice I'm not going to be offended by whatever answer I get.