>> "He wore that famous black mock turtleneck, Levi’s, and New Balances not to make a fashion statement, but almost for the complete opposite reason: so he didn’t have to think about what to wear"

If I recall correctly that's not true. He actually asked a Japanese designer to create a uniform for Apple employees. The employees didn't like the idea so Jobs decided if they wouldn't have one he would anyway and got the turtleneck designed.