In other industries you'd be mocked for wearing a hoodie to work. In this industry we mock you for wearing a suit to work. Hell, show up at most software shops in a pressed shirt and slacks and see what happens. Wear a tie non-ironically and we start assigning labels to you - "MBA", "suit", etc etc.
We've traded one superficial signal for another superficial signal, have no illusions about it. We've spent so long trying to be the anti-mainstream-business that it's no longer about letting people do what they want, and about conforming to the "cool software shop" cultural meme.
A very rich guy persists in wearing the hoodie he wore while doing the work that made him rich? Where do you see hypocrisy there?
Some people just rebel against the "norm" of using clothing to represent their socioeconomic status - money or no money.