It just shows how culture always trickles down from the top. Gates, Ballmer, etc are all tremendous dorks, and their dorkiness pervades the Microsoft brand. I suppose Steve Jobs' smartest move was recognising the importance of style, and having faith in his own good taste.
What's wrong with that? So he looks/dresses like one of those people who thought there was a spaceship hiding in the tail of a comet. If a certain type of clothes makes you feel comfortable, then wear them.
