I don't think he's trying to be something he's not at all. I think he's trying to be the person he wants to be, and fuck everyone else's opinions on what that should or shouldn't be. At the end of the day, he's the richest guy in America, possibly the world(?), and largely he did that through his own efforts. So who is anyone to tell him what he can and can't do? If he wants to wear a hoodie, he will, if he doesn't, he won't. No amount of gossip and rumour about whose nose he bent out of shape by doing so, or people trying to tell him what he should and shouldn't waear, is going to change that. People like Zuckerberg largely don't give a shit about gossip polls or rumours; and much as I may like or dislike what has been reported on his opinion or policies at Facebook, I can relate to his disdain for being told what to do... and I think truth be told, if everyone in the I.T. industry searched their soul for the truth, they can on some level relate to that. Most people that think for a living tend to have some level of a problem with authority... certainly given Silicon Valley's disdain for suits, I interpret this is more about defiance of societal social rules than trying to be something he's not.
No. I just think it's posturing on his part. He's pretending to be something he's not, so that people see the friendly brogrammer instead of the ambitious "They trust me — dumb fucks" CEO who disregards privacy.
Call me crazy, but maybe he wears hoodies _because they're comfortable_. That's why I do it, and I don't see how making a bunch of money would have any effect on that.