i think "cool" is relevant to your social group / age group.....
so, i wouldnt consider the CEO of my company "cool", but he is well respected by his peers, and i'm sure he is considered "cool" to them..
the same as i look at some of the kids at school these days, i look at what they are wearing, how they are acting, and i wouldnt consider them "Cool"... but i'm sure to their peers they are....
and a perfect example of "cool" can come from university (for those that have been)... there are so many different circles of people studying.... you have the sportspeople (well, we did at my uni..) the students who were into student politics etc, the party animals... i can go on with stereotypes... BUT if you talk to a girl who is into student politics, the guy with the dreadlocks who leads the protests is cool.... but the football player doesnt consider him cool, he considers him a feral... the footballer sees his teammates as cool... but the party animal wont see the footballers as cool, he will see them as jocks....... and so the circle continues...
i wouldnt know if i am cool or not.. if i go out, i dont care what others think of me, i just care if my mates think i am a great person to have around and i make them feel good.... that makes me feel "cool"....