The question of whether it's cool or unbearably dorky really has way less to do with any objective quality about it and more to do with uptake. If Apple mostly establishes themselves in the existing VR market (i.e. mostly a niche gaming device, with very scant general purpose use by an extremely small group of nerdy folks) it will be unbearably dorky regardless of how it looks objectively. If it's somewhat popular, even if (maybe even especially if) it's only popular among well-off people, then it will be considered cool.
Good points! Though I have to wonder... does "dorky" even really exist anymore in (my PoV) American culture? Maybe it does and I just don't run into people who think like that since graduating high school.
I'd personally describe the failure case, culture wise, as closer to "creepy" or "dystopian" or "out of touch/rich". I haven't looked into their materials too much, but hopefully it's super obvious if one of the many cameras on this thing is recording. Deep down I have a strong need to think Google Glass served some purpose, did some good, was not just a shudder in the cosmos to bring false hope to the few... I still want to believe.