Well it's no surprise when you have one of the most popular smartphones, that some people regard it as not "cool". This very sentiment was expressed on the Buzz Out Loud podcast last week (Buzz Out Loud 1333: Introducing the Ginsu Air). Is BOL still "Cool" - I don't care, I listen occasionally anyway.
As for the iPhone, when I decided to get an iPhone, just after the iPhone 3G was released, I didn't do it because I was "cool", I thought it would be a nice gadget. Now I still like the iPhone, despite its flaws, and use it more as a information portal and secondary gaming device than anything else.