How Jared Kushner — Kushner is Ivanka Trump's husband — drove his Range Rover around the Harvard campus when he was a student, according to "one classmate" quoted in "IVANKA AND JARED’S POWER PLAY/How the patrician couple came to have an outsized influence on a populist Presidential campaign" by Lizzie Widdicombe in The New Yorker.
I'm assuming "He didn’t do it with a sense of humor... He did it, like, ‘I’m fucking rich'" refers only to the way he drove his Range Rover, but it might also relate to the previous sentence: "On a campus full of T-shirts and cargo shorts, he wore dress shirts and jeans from the then trendy label 7 for All Mankind."
I'm trying to think about what it might mean to wear a button-up shirt rather than a T-shirt and jeans rather than cargo shorts in a way that could be thought of as speaking to onlookers and possibly being funny but also possibly being assholian. I'm thinking the perception would be in the mind of the beholder, the unnamed classmate.
The same goes for driving an expensive car. What possesses you that you would decide that a person driving a car is doing it not with a sense of humor but as a way to say I'm fucking rich? And by you, I mean the you that got into Harvard, so you must be pretty smart, eh?
But I can understand letting your jealousy show when some fellow student has an expensive car. It's quite something else to take a guy to task for wearing blue jeans when other guys are wearing cargo shorts. Ooh, he he thinks he so great... cargo shorts not good enough for him.... he's wearing jeans! And what's a "dress shirt" — just something that buttons up the front and has a collar and cuffs? It's not as if he went to class dressed like the Monopoly Man.