That's a Northern Californian look, not Southern. Generally speaking, you don't see Tech Geek Chic happening anywhere south of the Bay Area. If you live in SoCal, and the people with whom you associate are dressed as described above, you're doing it wrong. Find a better part of SoCal in which to live. For instance, I live in a very swanky and upscale part of LA because I am pretty awesome. He's right. In Southern California, you have to substitute flip-flops for the boat shoes.