This week Intersection, the New York Times' style video series, covered Oakland's fashion, specifically in the area around Lake Merritt. They interviewed a diverse group of Oaklanders, including a dandy barber/blogger, a designer, and a software developer. All seem to agree that the style in Oakland is diverse, and that it can be whatever you want it to be, which I think is pretty accurate. 

http://graphics8.nytimes.com/bcvideo/1.0/iframe/embed.html?videoId=100000002838328&playerType=embed