johnlawrenceaspden comments on Why Real Men Wear Pink - Less Wrong
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I agree with everything except your first paragraph. I've never had trouble finding perfectly normal clothing that allows me to sidestep fashion and merely look good. Neither have I noticed any particular social opprobrium for doing so, though I'm hardly at a maximal status (and my social circle is likely atypical), so who knows.
My impression is that it's always been possible (for men at least) to take the low-risk option and dress "conservatively".
A data point: My father bought me a beautiful and very conservative black suit for my Grandfather's funeral around 1994 when I was still a student. I liked it very much and wore it a lot.
The other day, looking for something to wear to a wedding, I dug it out and tried it on. It makes me look like a character from an 80's rock video, or possibly an episode of "Miami Vice", and I wouldn't be seen dead in it.
From which I conclude not only that there is fashion even in the most sober of men's clothing, but that I am aware of it in some way.
Both these conclusions surprised me.