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shminux comments on Call for Anonymous Narratives by LW Women and Question Proposals (AMA) - Less Wrong Discussion
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Comfortable is easy, comfortable but flattering is harder, comfortable, flattering but not sexy is harder still. Also, I suspect that when women say "comfortable", they often mean something other than what straight guys mean by the same term. For example, many women would say that wearing basic sweats and a hoodie in public is uncomfortable.
Um, high heels?
Sorry, I meant "clothes that I feel uncomfortable in," not "clothes that are physically uncomfortable." I would feel uncomfortable/less confident in sweats and a hoodie. I appreciate it was the wrong choice of words.