How to be cool
And the pursuit of timelessness
Why are we often so fascinated with what is cool? Perhaps because nobody, at any age, wants to be uncool. Unless, of course, we are purposeful in our “uncool,” which ironically makes us cool anyway.
One way to explain it comes from consumer decision-making professors Caleb Warren and Margaret C. Campbell at Texas A&M University. “Coolness is a subjective, positive trait perceived in people, brands, products and trends that are autonomous in an appropriate way.” (Appropriate, roughly meaning rule breaking without going too far.)
In other words, we consider people, brands and products cool when they realize and showcase their goals or attributes in their very own creative way. (1)
Let’s just say we wanted to be cool according to this definition, then how would we go about it?
We would need to both know ourselves and have an idea of how we relate to the current wider world, then stand in with self-expression. Be (or become) brave, about actions which make our view visible.
Then happily, again change it
It is said that fashion repurposes previous style trends in cycles of about 20 years. (The wide leg jeans of my teens, reinvented as today’s chic. Thankfully so far without plaid.)
Now I know that some people will call coolness, with its trends and cycles superficial. Yet I find it intriguing. What is “cool” changes as each generation responds to the world – provides insight when we dig deeper. Like the trend to capsule wardrobes in response to closets full of fast fashion.
Just look at the shift to gray glamour in the media, driven by demographics, such as the fun and beautiful advertisement gallery on Henry Barton’s Brand Builders Blueprint Substack. Where consumer spending power increases, there go the brands.
And Beth Bentley, in her Pattern Recognition Substack, describes how actually reading a book has come back into trend.
Where cool goes next
Feels to me that when coolness is authentically grounded in the individual, timelessness may follow. Audrey Hepburn, Coco Channel, James Dean. All cool in their moments and timeless over the decades.
As a young girl, I was for while on a local fashion board. (Let’s get a clear small town picture here: I also handed out trophies to cows and pigs as a fair queen.) There, we discussed that matching the cut and fit of our clothing to our body type was equally as important as grabbing the latest trend.
I ask myself more and more these days, why not apply a timeless-cool philosophy to other activities and goals. Repurpose ourselves every so often. An expected cycle over decades. Keep what we view as iconic and choose which coolness in the current culture also attracts us.
Be conscious about it. Enjoy it. A repurposing cycle would require us to stay curious about how the world is evolving. To use whatever are our favorite resources to do it: conversation, reading, listening, traveling, etc. To say “I want to explore that, try it” instead of “I don’t get how the other generation thinks.”
To be open, explore and then choose. Timelessness as a basis, with a nod to the cool that is you.
Footnotes
(1) As described in The Atlantic (2014, Derek Thompson) and directly published in the Journal of Consumer Research (1014 Warren, Campbell, Texas A&M University)


