I'd wear chucks so I could be cool, but they hurt my feet, and I wore them enough when I was a little kid and they weren't cool

I even have flat feet, so it's not the arch support that's the problem, more the fact that the soles are like walking on steel and have no cushioning.
For work, jeans, shirt, hoodie, depends. In summer, whatever i can wear under my gear and not overheat, and in the winter, whatever I can wear to keep from freezing. I keep hoodies & such at work in the summer because I am closest to the A/C and furthest from the thermostat so it gets ludicrously cold in my office.