Among other reasons, he won't wear a hat because he overheats in 70 degree "heatwaves" or any time direct sunlight hits his window. He has refused to wear various hats and costume headgear due to his intolerance of even the merest possibility of warmer temperatures.I wonder why wearing a hat all the time apparently isn't an option? I assume it's because Phil doesn't merely want to hide the fact that he's bald, he wants to live in denial of it. Total Biscuit had an even worse balding problem than him, and so wore a hat most of the time, but he wasn't acting like it was getting ruined by headphones or some other bullshit. He wasn't lying by wearing a hat, he just didn't like how he looked without it.
It says a lot about Phil the fact that in his attempts to turn his rep around, he relies on Twitter's ignorance rather than look at the e-celebs who are or will be remembered better than him. He doesn't want redemption, he wants people to memory-hole everything bad about him just like he does.