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I'd argue that cool is only definable in the rearview mirror. That in the now we are all just fulfilling our own personal preferences and then 10, 15, or 20 years later we can look back and decide which of those many activities, trends, subcultures, etc., were actually the cool ones.
At the time you'd probably pick disco as the winner based on popularity but 20 years later it is cooler to have been into punk.
I do agree that popular and cool don't have much overlap. Because we all know, instinctively that being cool is reserved for an exalted few. Therefore if it had mass involvement it can't have been cool. However, being cool also requires being ahead of the curve, being a trendsetter not a trend follower. So the cool among us are doing things that few people do now but in five years everybody will either be doing or will claim to have done (the total claimed population of Woodstock: 2.6 billion; number of people who voted against Reagan in 1984: 98%).
So, since in the rear view mirror that which was cool eventually ends up looking like that which was popular, even though the cool phase preceded the popular phase, as we move to trends closer to contemporaneous periods we are tricked into confusing the currently popular with the currently cool. When in fact, what is now popular will be mocked as a bunch of sheep in 4 years when VH-1 does a nostalgic look back on 2007.
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