I think the reason it's so interesting/weird to look at is that, on the one hand, the hair looks too poofy, and, on the other, it looks too short. That is to say, the poofiness doesn't fit the stark geometry (which is usually only seen with very closely cropped hairstyles), and you end up with some sort of…

Well, because he's doing more important things than picking seating arrangements.

You could prove the first ten axioms of Euclid's Elements with that haircut of his. What was going through his rapey little brain? —"Hey, I'm going to sit next to the First Lady of the Nation. Give me a haircut that makes me look like I have the gardens of Versailles on my head." Fascinating.