http://www.paulgraham.com/bubble.html
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5. Informality
In New York, the Bubble had dramatic consequences: suits went out of fashion. They made one seem old. So in 1998 powerful New York types were suddenly wearing open-necked shirts and khakis and oval wire-rimmed glasses, just like guys in Santa Clara.
The pendulum has swung back a bit, driven in part by a panicked reaction by the clothing industry. But I'm betting on the open-necked shirts. And this is not as frivolous a question as it might seem. Clothes are important, as all nerds can sense, though they may not realize it consciously.
If you're a nerd, you can understand how important clothes are by asking yourself how you'd feel about a company that made you wear a suit and tie to work. The idea sounds horrible, doesn't it? In fact, horrible far out of proportion to the mere discomfort of wearing such clothes. A company that made programmers wear suits would have something deeply wrong with it.
And what would be wrong would be that how one presented oneself counted more than the quality of one's ideas. That's the problem with formality. Dressing up is not so much bad in itself. The problem is the receptor it binds to: dressing up is inevitably a substitute for good ideas. It is no coincidence that technically inept business types are known as "suits."
Nerds don't just happen to dress informally. They do it too consistently. Consciously or not, they dress informally as a prophylactic measure against stupidity.