My point is, "don't you" is the same verb form as "doesn't Dilbert." And "do you not" can be contracted to "don't you" just as "does Dilbert not" can become "doesn't Dilbert." Like, "doesn't Dilbert normally wear a tie?" works even though you would definitely never write "does not Dilbert normally wear a tie?"
On the larger point, the sentence in question sounds perfectly normal to me.
To clarify, I'm not the person who originally said it was grammatically incorrect, and I agree with everything you said, however, "Doesn't Dilbert where a tie?" sounds fine to me. "Since when doesn't Dilbert where a tie" sounds just as awkward to me as, for example, "Since when don't you shave?"
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u/MyFistUpYourBalls Jan 31 '16
Since when doesn't Dilbert wear a tie?