> It's almost as if, once you get to a certain level of power, you no longer need to try.

Correct. I think it's also a bit of a shibboleth now, like not wearing a suit. In former days the lower ranked employees wore jeans, t-shirts, hoodies, etc. and the bosses all wore suits and ties. Now it's the opposite at least in tech. If you see someone in "business" attire, you know they're middle management or sales and have no power, where if someone is in a tshirt and jeans they're probably a founder or executive. It's a flex to dress casual.