Earlier quoted context omitted.
What I'm hearing from many posters in these comments is my level of fashion-conciousness indicates how innovative I am. I think it's a big mistake to judge a candidate's aptitude for the work by how hip they look. This is the last industry I thought we'd have to face this kind of thing in.
Well, wait. I've always said this too: it shouldn't matter how I dress. But the truth is that dress is very frequently an indicator of how aware one is. It's a social consciousness that is sometimes reflected in other things (like being able to adapt to a new technology). Look at this comic: http://xkcd.com/1139/ - the playground jerks call the guy a loser because he isn't playing the social game. They are right that…
At the CEO level, I'd argue that you must look for people who understand the value of understanding their target audience ("customer") and taking the low cost / low friction action required.
Or, put simply, spend a couple of hours and $200 on cloths to look the part.
What, exactly, do you think would happen to a 24 year old hotshot banker who goes to an interview at, say, Goldman Sachs wearing Bermuda shorts and a t-shirt?