Zuckerberg and Steve Jobs wear their trademark basic tee and jeans as a sign of status. It shows that they can break away from convention without getting penalised by society. Wall Street can’t affors to ignore them even though they are not in their fancy suits.

Their dresscode isn’t a sign that they don’t care about how they’re perceived. In fact, I think it’s the opposite. It’s still a show of status because it proves they are above social conventions.

I’d also wager that their basic clothes costs a lot more than what the average person can afford.