As soon as someone refers to something as being "cool," in the minds of those who do not care for coolness, it immediately becomes "kitsch." This is but one example of how modern aesthetic categories are used to indicate political hierarchies. Everything that classical texts like Zur Genealogie de Moral refer to is applicable here - you generally swap out the analysis of how religious language evolved, with an analysis of how the language of aesthetic critiques evolves. Coolness, in this sense, is political in the same way that religious language is political.
The longer I listen to people talk about what is cool, and what is not, the more I grasp the concept that coolness is a currency of the aspiration yet skill-less aesthete. The economically unencumbered individual has less incentive to avoid kitsch, as the word "kitsch," simply functions as a mark made by the unencumbered upon the encumbered individuals who aspire to disencumberment. Indeed anything that the masses refer to as kitsch, which is then publicly endorsed by a celebrity, stands a decent chance of gaining reference among the masses, as cool.
At some point in the 1940s it was a minority subculture to be hep, or hip, meaning that you had a good sense of jazz music at a time before most people knew what jazz music was. Since the 1990s, of course, those who identify with hipsterism have all but regurgitated everything that is old, bringing nothing new from any decade, in fact, seeming to function purely as a niche term for "yet another subculture," or "post-boho-boho."
What is cool, is not a question, but a choice. And the easier it is to predict someone's choices, the easier it is to anticipate their sense of cool. And that is what players do.