Wearing shirt collars turned up: cool looking, or goofy?
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Depends. On a guy, goofy. On a woman, sexy.
I don't think the look is one size fits all. One could look cool or even sexy. On me, goofy.
Depends on if you have traveled back to the 80's and are a yuppie. Otherwise, decidedly cringe-inducing and always mock-worthy.
Ever since I saw this picture, I've decided that popped collars are not cool. At all.