Why dressing well only gets harder as we get older

I live across the road from a popular fast-fashion menswear chain, the sort that sells affordable but on-trend items. Every time I leave the house I pass the mannequins that line the window, and every day their outfits have changed ever so slightly; the dark winter coats making way for light spring jackets, which in turn make way for summery pastel shirts.

It's a lovely – and perhaps the only – way to mark the passing seasons in Melbourne, where the weather has two moods: "Soviet Drizzle" or "On Fire".

This year, as summer finally turned up muggy and grumpy, the mannequins starting sporting jaunty chinos, and, curiosity piqued, I entered the store for the first time.  

What do men even wear?

A confession: for say … oh, the first three decades of my life, I had no idea what grown men were supposed to wear. There were the tracksuit pants one wears as a child, then the scratchy, uncomfortable slacks of high school and stacking supermarket shelves, and after that … cargo pants?

I knew about suits. I've seen them in the wild, and I've even worn them – to weddings or just everywhere for a week after a James Bond film comes out – but I'm not in a line of work that requires formal attire. In fact, I only have one suit, a slate-grey three-piece; hand-made for me by a tailor in Bangkok who kept trying to gently up-sell me on a matching cravat and a pound of weed.

At a certain stage of life, when you undress in front of your doctor, they start to make that same distressed noise a mechanic does when they pop the hood on an un-serviced Corolla.

Those awkward (older) years

When you are young and in fine shape you can get away with a lot more. On your 29th birthday it's fine to be down the pub in a Bintang singlet and jeans, but the second the clock ticks midnight, you had better be in a neatly ironed button-down and sneering into a glass of uninspired merlot, or you quickly start to look like a sex tourist.

A man starts paying more attention to the way he dresses as his body betrays him. As youthful fitness fades, clothes become an immaculate cover for the eldritch horror that lurks underneath. At a certain stage of life, when you undress in front of your doctor, they start to make that same distressed noise a mechanic does when they pop the hood on an un-serviced Corolla. A little while after that, your partner starts doing the same thing.

Clothes are linked to identity. We use them to signal to the world who we are and where we are in life. A such, they have an expiration date.  

The things that once worked for me no longer do. The other day when I put on an outfit to go to a hip-hop show, I looked like I'd dressed as a cartoon burglar for Halloween. I own a classic black leather jacket that, should be, theoretically, the gateway to a certain normcore chic, but I couple it with boots and a scarf and suddenly I'm cosplaying as Marvel's Jessica Jones.


The mannequin challenge

I stood on the pavement outside, staring at the mannequin, admiring how carefree he looked in his smart casuals. He seemed to embody the precise degree of rugged, relaxed, sophisticated manhood I hope to grow into. This plastic man with a yacht-sweater thrown over his shoulders. He was living my best life.

I buy the chinos, two pairs. They begin to fall apart immediately. If they aren't washed, dried, and ironed in extremely precise ways, the seams explode like the narrative arc in a Michael Bay film. They soon become the highest-maintenance relationship in my life. I come to realise my mistake. Fast fashion is an unethical investment at best. My shiny pants were sewn in airless factories by tiny fingers and are designed to fall apart after three months, when the next season's trend has come in.  

It serves me right for buying fast-fashion chinos. Hemingway would not have shopped at a chain store. He would have taken his from the body of a man he'd killed in an arm wrestle. It was daft to try and emulate him, but, isn't that what fashion is? We buy an outfit to try on an illusion, be someone else for a minute.

Now that I think about it, I've probably over-thought the chinos, but I've got a lot of time to think, because now I have to spend half my life ironing pants, which is, I suppose, something grown men do, after all.

Is it harder to dress your age as you get older? Let us know in the Comments section.