> Everything about his clothes screams “down to earth,” “humble,” “stoic,” “thoughtful,” etc.

It's a jean and a hoodie. I think you are reading bit much into it

Maybe the dude knows he can get away with a pretty comfy sweater t-shirt jeans combo, so he does.

What would the appropriate attire be?

Reading too much into it: public figures have rationalization for what they wear, and a lot more insignificant things. But yes, I’m not saying this guy in particular. I’m not reading into him. It’s about the wide-spread trend. He’s just following the trend.

He’s just being comfortable: a $4000 bespoke silk suit is a lot more comfortable. And trust me this guy probably owns a few garments in that category.

What should he wear: I’m not saying this guy is horrible for choosing to wear this exact garment. He’s following a negative trend, and my comment is about the trend. “God do I hate the fashion of SV,” please read stuff before replying.