I am looking in a shop window in Oxford Street when I hear someone call my name. I turn around and there are Minnie and Maisie, two of my 13-year-old daughter’s school friends. They are trendy young things off for some light consumption at Topshop; I am a middle-aged man dressed in a little Whistles skirt/Monsoon jacket combo and look a bit like an off-duty Duchess of Cornwall. I don’t get many opportunities for leisure trannying these days so I used the occasion of shopping for my wife’s birthday present to don a housewife-up-from-the-’burbs number.

Now as a rule I would say that if there is one group of people that transvestites need to avoid, it is early-teenage girls. They study women and will notice any aberration — and they are not scared of yelling their findings across the street. But my daughter goes to a lovely school and her two friends seem unfazed, there is no tittering (well, not to my face anyway) and we have a delightfully civil exchange. In their eyes I thought I could see a three-way struggle between wanting to laugh (which would have been OK, as I’m the first to admit that it was a funny situation), being polite (as they are nicely brought-up girls) and being cool (should they act as if meeting a classmate’s dad en femme hardly warrants a ten-character text?). The encounter lifted my spirits, and their acceptance of my foibles was a positive outcome of them being hip metropolitan children.

Kids are incredibly learned in the laws of cool at a very young age these days and that’s fine, because cool is a code that helps them to navigate through the embarrassing pupation of adolescence. It’s when coolness infects adult discourse that I hear myself sighing.

Cool is a word that often crops up when describing art or artists. It’s always been a term that has bugged me. The minute something is described as cool, my instincts tell me that it is on the wane. For me, being creative is being prepared to make a fool of myself — in a nutshell, the opposite of cool. In my experience embarrassment is not fatal. Coolness somehow implies that there is a right thing to do, whereas creativity is mistakes. I recall in sixth-form art lessons that the coolest boy just churned out copies of his favourite album covers. Maybe he could not allow any of his messy, wistful, unformed self to spill out through a chink in his carapace of cool.

Few groups can be more conservative than teenagers who take coolness seriously: they pounce on difference; goodness is boiled down to the lowest common denominator of “correct” brands, bands and overwrought hair. What makes cool an immature value system is its simple hip/square, in/out, mingin’/blingin’ binary, while being adult is dealing with shades of grey and with compromise. With luck, as we mature we can trust our judgment about what feels good or bad. We can cast aside the crutches of cool.

My generation has grown up steeped in the argot of cool. There are many people of my age who still seem to think that the value system of a teenage boy applies to grown-up life. Perhaps it’s time to chuck the Pete Doherty trilby and take the surf-shack sticker off the back of your car, for cool is the new straight.

It used to be in the 1950s that a small coterie of bohemians in Soho or SoHo would exude coolness while the squares just got on with earning money to buy stuff. Now a large proportion of consumers hope in their heart of hearts that their choices make them seem cool. Whether we are pulling up at the traffic lights, strutting down the street or nodding meaningfully in a club, to aspire to be cool is to aspire to be an average consumer. While riding my motorbike, I sometimes catch myself looking at my reflection in shop windows, hoping to see a fleeting vision of Dennis Hopper, when in fact I know that I look like Peter Stringfellow propping up his virility.

To be seen trying to look cool is inevitably, to look the opposite. In years to come we will look back at our obsession with appearing cool as we look at the medieval chivalric code. I think the time has come for adulthood and wisdom to be seen as things worth aspiring to.

For hipsters of my daughter’s age though, cool is cool. She was recently named in an article in The Independent as one of the 50 coolest kids in Britain for her work co-designing the Old Vic Panto. Being genetically sub-zero, she couldn’t be bothered to read it.