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We use the phrase to refer to men who might, at that moment, be wearing something entirely different than a suit. But I've never heard someone say "he's an empty pair of khaki pants and a work shirt." And that's because the phrase doesn't actually refer to what they are literally wearing at all. It means: "an ineffectual executive" or a phony who's pretending to know what they are doing.
But we keep (and by we, I mean Jim) drawing attention to her GENDER every time we alter that turn of speech, in a way that puts that front and center. We're not altering it because we are so concerned that we will misrepresent what she wore at a particular event - the details of what she wore at a specific event is a nonissue, just as it's a nonissue for men.
What Jim's drawing attention to is that she's not just an ineffectual executive, but that she's OMG an ineffectual FEMALE executive.
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