Mayor Jean Quan of Oakland recented compared Oakland to Brooklyn.
Peter Lawrence Kane of The Bold Italic sees if this comparison holds up:

How cool is Oakland? Well, Manhattan is the global capital of all media. Brooklyn has Girls and writers named Jonathan. San Francisco has Looking, the newest Real World, and Blue Jasmine, as well as Twitter, Yelp, Reddit and all the rest. Oakland has Pandora and a growing number of high-profile tech companies, but not nearly as many ­- and there lays part of its charm, at least for now. Oakland is considered cooler by not being quite as marketable, because Manhattan and San Francisco – and, rapidly, Brooklyn – are taking coolness down with them as they ascend up out of reach. The human body is exquisitely attentive to a certain calculus wherein it feels its movement relative to everything going on around it, not just from geographical center to periphery but in the vertiginous up-is-really-down movement of the city and desire.
I lived in Manhattan for 12 years, 5 of which were in the the East Village—still one of the best neighborhoods in NYC. My brother moved to Cobble Hill in Brooklyn a few years ago and I will admit, if my wife and I ever move back to NYC, Brooklyn is one of the top places I’d consider moving to.
From what I’ve heard from natives here in San Francisco, Oakland doesn’t have BKLN Cool Status yet.