The funny thing is, casual clothes often take more thought. With a suit you can blend in, with casual clothes, even if they're not great, they're /yours/; no hiding from your choices. Sure you can screw up a suit too, but it takes a lot more trying. As long as it fits well and it's not weird, it's a suit. There's not a lot to think about. It's basically like the classical Jobs' uniform of jeans+turtle neck, but way better looking. Unfortunately it now has the stigma of being "stuffy".