Cool isn't just a style. It's a state of mind.
Here's a theory...
The clothes I wear are a small glimpse into me, into anyone. What is key is how the person in the clothes not only carries themselves, but how they see themselves. I can wear whatever I choose, from a well-cut suit to a Canadian hockey jersey to sweater, or a daishiki. It's how I carry myself in them that counts.
This comes from a story about Barack Obama's style. What he wears on the campaign trail isn't vastly different from everyone else. What is different is that he carries himself much differently than Mike Huckabee or John McCain.
Hastreiter still sees a kind of cool embodied by the likes of Miles Davis, Mick Jagger or the beat poets. It is a 1960s version based not on attire but on confidence, self-satisfaction and life philosophy. The cool cats seemed to be living to the rhythms of a personal soundtrack. That notion meant something; it had longevity. Who would declare Jagger uncool even today?
So, do clothes make the man, or does the man make the clothes? In Obama's case, I'd argue for the latter. The clothes are the outward embodiment of the inner confidence of the wearer.
Cool lasts longer than 15 minutes, not because of the staying power of the clothes, but the staying power of the person in them.
If I'm wrong, tell me. Correct me.