This is definitely not the case outside of tech, and generally not the case for firms headquartered outside the major US West Coast cities. My line of work exposes me to the senior leadership of major US and global firms across the US in a wide spread of industries (tech, energy, pharma, medicine, industrial suppliers, consumer goods, automotive), and there is an almost universal expectation that middle managers and above will be dressed in business casual attire, with one's clothing becoming increasingly formal the closer one is to the top of the management pecking order.

Labor in working overalls is salt of the earth type. Senior exec in a suit is an empty suit. When labor makes a bad decision it only affects that person. When an exec makes a bad decision they are usually the ones not affected.

The hoodie CEO is GenX/Millenials attempt to get not appear as the empty suit. To announce that they are from working class even if they are not.