I think a wearsthis site, similar to usesthis.com, would be quite popular. I'd like to know what shoes Spolsky is wearing, what t-shirts pg prefers, what brand of underwear Drew Houston uses, and, of course, where does Zuck gets his hoodies (they are custom made: http://www.quora.com/Mark-Zuckerberg-1/What-brand-of-hoodie-...).
While coding (and especially when I'm hung up on a problem) every little distraction, even miniscule, distracts me, so I hate wearing shirts, I have to wear t-shirt. I've yet to see t-shirts that are marketed predominantly for coders, say, with a nice quote on them (e.g. ""Metaprogramming is the language feature that helps you write code that you won't be able to understand once the cocaine (or Ritalin) wears off."") and the ASCII table on the back.