How a hat became my guide to aging well

Why I wear a dad cap

I've never been much of a hat person.

But lately, I've found myself reaching for what the culture calls a "dad cap".

You know them: those soft cotton, unstructured baseball caps with a curved brim with usually - through age or intention - a slightly faded look that evokes an early-to-mid nineties vibe.

Their history is interesting. Apparently in the late 80s, cool kids began modifying traditional baseball caps by removing the buckram (the white stiffening material) from the front seam to achieve a more relaxed fit that moulded to the head, with the brim curved into a perfect parabola. They would put their caps through the washing machine to wear them down faster.

By the 2000s they became ubiquitous. Cheap and easily branded, stocked in goodie bags at every corporate event. The dad cap became, well, fashion for dads. Out it went!

That is, until it cycled back into fashion with celebrities and influencers in the mid-2010s, where it has stuck in the mainstream culture since.

In the summer months - as the husband to an Italian - I wear them to protect my face from the battering Italian sun, and over time, I've accumulated a small collection.

Among them, one cap stands apart – an olive green Apple Computer cap from the heyday of their nineties merchandising. It features an embroidered version of the Apple logotype from that era, in that slightly condensed Garamond font they used back then.

This cap wasn't originally mine.

It belonged to my best friend. It was given to me, by his father along with a few other mementos, after he died.

Ian - the dad - was one of the early sales directors for Apple in the UK during the early/mid 90s – a position that came with its share of company swag. It imbued my friend with some serious nerd credentials. He had Apple keyring, rare Apple posters, and an encyclopaedic knowledge of the product line. It was the thing we first bonded over: our love of those rebellious, counter-cultural computers.

When he died, Ian decided to share his son’s possessions to his friends, and he knew how much I loved and adored these bits of nerd swag. I’ve held onto this cap for 23 years.

The funny thing is that I only started wearing it last year.

For all that time before, I kept it purely for sentimental reasons. It has followed me from Edinburgh to Glasgow, then to London, packed away with my clothes and collections of things.

For nearly two decades, it didn't seem like a very cool thing to wear, until I became a dad myself.

Although its the fashion to wear ‘dad caps’ even if you’re not a dad - much like the boyfriend tee or the lesser known girlfriend jean - to me, it signifies something a bit deeper than fashion.

This cap is an artifact. A signifier.

It represents an essential component of an aesthetic of one of my favourite types of men: elder hippy dads.

These are the men I aspire to be.

They embody a spirit, values, and sensibilities that don't come naturally to me, but which I try to cultivate as I age.

Think Zen Buddhist and founder of the Zen Hospice, Frank Ostaseski in his Be Here Now cap.

In fact, think of his friend and progenitor of the phrase ‘Be here now’, Ram Dass.

Think mycologist Paul Stamets.

Think Steve Jobs actually looking relaxed with his family.

The cap represents a relaxed attitude toward life, a letting go. Being outdoors in the sun, feeling comfortable in your own skin, not trying to be cool but being cool precisely because you're not trying.

When I put on a dad cap, I do so with an intention to relax into a mindset of easiness, a way of being that feels authentic and unforced. It’s the kind of dad I want to be.

It sounds like this humble cap is doing a lot of heavy lifting, but there’s another thing I realise with it.

I don't expect to achieve their level of awareness or attitude of my spiritual north stars like Ram Dass, or Frank Ostaseski, but they are my template for growing older.

And therein lies the poignant, bittersweet realisation – my friend, who died at 17, left me a cap that he wore as a kid, which I now wear at 40.

Wearing this cap at 40 has become a symbol to me of how I want to grow old: with grace, good humour, and joy.

So this humble, faded Apple cap is an object carrying memories of youth now becoming a talisman for aging well. The cap that once sat in boxes, following me through the chapters of my life, now sits on my head as I write the next ones.

It reminds me daily that the best way to honour those we've lost is to live fully into who we want to become.