Is it some form of "rebellion"? Or is it to show they have so much of a certain kind of intelligence and that they "rule the world". They can do whatever they want with the iron fist of "whimsy".
This isn't the same as some teenager who used to dress up as a "punk". That style was to show a separation from society.
The new "geeky corporate style" is to show they ARE society. They rule society and use their *certain kind of intelligence* to rule. They're not turning the olden corporate symbols on their heads. They're saying they ARE the new corporate style.
They own the secret knowledge. You cannot join the "club".