khafra comments on What do bad clothes signal about you? - Less Wrong
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Michael Vassar has advocated wearing a fashionable, well-fitting suit with Vibram Fivefingers to properly countersignal--since without showing the capability of properly signaling, the "counter" part is lost.
If I saw that, I would assume the person was trying to make a statement, but I would not be very receptive to it since those things look ridiculous. It's like applying an Uncanny Valley skin to your feet.
But their looking ridiculous is part of the point!
Vibram Fivefingers look hideous to be, but sometimes I wear fashionable clothes and then put on a ridiculous rainbow fedora hat with paillettes.