The Zen of Cool

Chris Reads
6 min readMar 5, 2021


This past week, I started reading Island, another one of Huxley’s utopian political parables, but more overtly dogmatic than Brave New World. Or perhaps I’ve just become more aware of veiled politics in writing as I’ve aged. I haven’t finished it because I’m book clubbing it, but near the beginning of the novel there was a passage that I thought tied together these thoughts on coolness that I’ve had for a while:

“Knowing who in fact we are results in Good Being, and Good Being results in the most appropriate kind of good doing. But good doing does not of itself result in Good Being. We can be virtuous without knowing who in fact we are.”

This passage was taken out of context and heavily wrapped up in some exotic spiritualism as I understood it. However, replace “Good” and “good” with “Cool” and “cool”, and I think it accurately conveys my ideas on being cool: the ultimate state of Cool, with a capital C, is complete knowledge of oneself, and all derivative cool, with a lowercase C, is only so because it signals this knowledge. More on this later.

I conducted two searches on Google as I wrote this piece, since DuckDuckGo doesn’t show number of search results. There are 1.4 billion results for “what does it mean to be cool”, and even more tellingly, 11.5 billion results for “how to be cool”. I understand search engines are finicky and this data is circumstantial at best, but the same search for sexy, smart, and rich return 3.1, 3.2, and 1.5 billion results respectively. At a minimum, “coolness” can be understood to be a elusive and unknowable, yet highly desirable and obtainable trait. Though Cool can’t be pinned down, examples of cool are readily found everyday. Identification as cool is broadly positive and attributable to virtually everything. Physical things and intangible ideas, activities and persons, or movements and aesthetics, everything can be considered cool.

Before “cool” became an enviable quality, it was the antonym of “warm”: a little more heated than cold, but still closer to cold than hot. Etymonline attributes its figurative use in English to as early as the fourteenth-century, in reference to more detached personalities. Its modern usage has been traced back to Jazz saxophonist Lester Young by cool historian, Joel Dinerstein, who has his own interesting ideas on Cool.

Unsurprisingly like much of American popular culture, the original Cool had its roots in African-American culture, which in turn has its roots in slavery and rebellion. As cool philosopher Botz-Bornstein writes, black slaves developed a cool attitude as a defensive mechanism, balancing a provocative resistance to authority with a necessary appearance of submission, where even today the “angry black man/woman” stereotype costs lives.

It’s simple to dissect Cool through analyzing how this original Cool was co-opted. The survival strategy gives way to a copping method for black people who were otherwise blocked from traditional white paths and definitions of success, providing an aspirational identity that doesn’t attract negative attention. Cool is then seen as a counter-cultural trait, picked up by rebellious teenagers who lent it youth and a whitewashed veneer. Cool is still imbued with the self-control and composure present in the defense mechanism, but subversion is often traded for difference and exclusivity, in the American Classical Cool.

The Classical Cool is embodied by the tough-guy acts of Humphrey Bogart, James Dean, Alain Delon, and Sean Connery. Emotionally distant and self-confident leading men defined what it meant to be cool for a generation: a softer defiance that was angsty enough appeal to the mainstream while remaining something parents wouldn’t like. The Classical Cool was also reserved exclusively for men: Georgia O’Keeffe and Simone de Beauvoir were admired for their work, but ahead of their time. The preferred personalities were those of Grace Kelly, Audrey Hepburn, and Marilyn Monroe, neatly fitting into preconceived gender roles.

The Classical Cool hangover persists to this day: Cool has been long separated from its roots of oppression and persecution to a marketable essence, characterized by aloofness and confidence, the cool that the older generation believe in, yet ironically despise in youth. Yet the younger generation has its own ideas of cool, which have overlap, but are incongruent with Classical Cool.

Dogs and cats are both cool. Drinking unique craft beers and Pabst Blue Ribbon are also both cool. Talent at chess and excelling at fencing are both equally cool. Being a reserve for the city orchestra and opening at the local dive on Friday nights are also both equally cool. Emma Watson and Billie Eilish are cool like Fonzie. Being able to cook and knowing how to change a tire are, weirdly enough, cool as well.

A 2012 study asked 508 adults with an average age of 21 to list words that they identified with Cool, and the top trait categories were surprisingly pro-social and positive, such as friendly, personally competent and trendy; the Classical Cool traits of unconventional, confident, and emotionally controlled made fewer appearances, but continue to linger, especially when participants were then asked to rank these traits on a spectrum ranging from social desirability to coolness.

Many consider this evidence of the degradation of the English language, particularly schoolteachers fearing an Orwellian descent where everything is either Cool or not Cool. What nuanced meaning does Cool retain when it seems to denote every positive trait? It is difficult to identify Cool when there are so many cool things, actions, ideas, and people, that it starts becoming a synonym for good.

This is where I’d like to paraphrase Huxley:

“Knowing who in fact we are results in Cool Being, and Cool Being results in the most appropriate kind of cool doing. But cool doing does not of itself result in Cool Being. We can be cool without knowing who in fact we are.”

I posit that everything that can be considered cool is only so because it suggests that the subject to whom they belong is Cool, whether this is true or not. This Cool lies in self-awareness and self-possession, and ultimately in understanding of oneself, as well as the situation one is in.

Black people in America were the progenitors of the original Cool when they came to understand the uncompromising realities of their situation, and how to survive in spite of it. Classically Cool Rick Blaine, Phillip Marlow, and James Bond act confident and uninterested because they understand what they’re capable of and what they need to do, acting with a single minded determination towards their goals. The posturing and posing, deftness and difference can be emulated to appear cool, but will never capture their Cool.

Variation in taste has grown with the explosion of the internet, lending itself to different subcultures even within a generation in the same country. Despite the number of new norms, people can perceive Cool within different affiliations more than ever. But this is easy to emulate, especially to an outsider without an understanding of that culture. If skateboarders or coders all like certain graphic t-shirts or stickers, having those items suggests membership to that group to the uninitiated. Likewise, a studied indifference to an activity or idea implies sufficient knowledge in the area to develop an opinion, whereas its often just an unwillingness to participate.

This has caused friendliness and humility to become cool traits in a world of poseurs, because they demonstrate both an understanding of oneself, as well as an indifference to the masquerade. This is similar to how dressing down was Cool because it showed that the wearer had enough clout that clothes didn’t have to contribute. Of course, subsequent emulators who dressed correspondingly in to signal an association with the celebrity style missed the point entirely. They were chasing a cool look instead of Cool.

So when people peruse the 11.5 billion results for “how to be cool”, they’re missing the forest for the trees; Cool people do cool things because they understand themselves. To emulate cool actions without being Cool is to pursue a red herring, and wave it for everyone to follow as well: but cool doing does not of itself result in Cool Being. Some simply crave the esteem and respect of others, or have perhaps decided that this sort of mimicry serves their ends. But Cool Being results from knowing who one is, and Cool Being results in the most appropriate kind of cool doing.