Do you know why looking like Cory Doctorow works for Cory Doctorow? It's because of his full-on geeky enthusiasm. No, really. It is. If you get his haircut and his glasses but not his gadgets and passions and knowledge about both, it will not work for you. Get a different haircut and glasses. Seriously. They're not very universal. Something else will likely stand you in better stead. I would advise you to also get things like passionate interest in nerdly topics, but the haircut and glasses are bound to be an easier thing to start with.
The sad thing is, I doubt that those particular guys were attempting to look like Cory Doctorow specifically, and yet I can't see any other good reason why those sartorial choices should get made.
There are things I love about retro fashion (bell! sleeves!), but one thing I really miss is the attempt to look futuristic and not just look like what people used to think futuristic would look like.