While no one bats an eyelash at women wearing "men's style" flats, eyebrows are still raised when men wear heels. –Especially if they are not onstage or in drag. Despite the public's general discomfort with men who wear clothes or shoes considered feminine I've observed more men out & about in heels –and not just at the gay venues. I personally love this as a trend because I think fashion should be fun and exploratory and not limited by gender. And I happen to like this guy's whole outfit.
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