I’m sure he gives half a flying **** what a load of tedious middle-aged IT managers think of him
I actually think he cares a great deal what everyone thinks of him.
Exactly.
If he didn’t care what people thought of him, he’d be wearing jeans and a teeshirt, or any other stuff you can buy in every clothes shop or supermarket in the world.
The only reason to wear that stuff is because you care what people think.
You probably want some of them to hate it, but that not the same as “not caring”
It’s done for attention, either negative or positive, makes no difference.