Oftentimes, our past style transgressions materialise painfully, as Facebook Memories that we don’t much care to be reminded of. But unless you popped out of the womb on-point, then at some stage you’ll have had some skeletons in your closet. Even if you subsequently destroyed all the photographic evidence and gave the skeletons to the charity shop.

Disclaimer: this is an entirely subjective recounting of one man’s odyssey through the choppy seas of wearing clothes. The hope is that you’ll recognise some of these checkpoints from your own personal journey, learn from these mistakes and avoid going off course.

Stage 1: The Awakening

I can pinpoint the precise moment when I realised that clothes could say more about me than my fondness for Arsenal Football Club or Thundercats.

I’d just started at a new secondary school – not the local one to which all my primary school mates went, but a fancy one a few miles up the road where the pupils were from very well-off families. (I’d landed an academic scholarship which pretty much covered my fees.) Bookish and bespectacled, I looked like Harry Potter before it was cool. I yearned to fit in, to be cool and popular. I did not, and I was not.

In my class was a cool, popular boy who also possessed a stripy jumper. Now, I may have been confusing correlation and causation – understandable, at the age of 11. But I remember clearly thinking that if I had a similar stripy jumper, then I too might be cool and popular. This seemed like a reasonable hypothesis.

I asked him where he bought the stripy jumper from and he named a not particularly cool or expensive store in my local town. I think it might even have been Officer’s Club. I went there, and bought a similar jumper – in a different colour, lest I be labelled a copycat. But to my disappointment, it didn’t have the same effect. So I turned my keen young mind to the question of why. After all, its constituent parts were the same. But perhaps the ratios were somehow out of whack? Or was it the other items I wore with it? It was a mystery wrapped in an enigma wrapped in stripy polyester.

It was around this time that I started becoming aware of brands. There was another cool, popular boy who had a sweatshirt bearing the Calvin Klein logo (an original nineties one at that). He also wore eau de toilette – Acqua di Gio, by Giorgio Armani – which struck me as the height of sophistication. The Nicks trainers that my mum wanted to buy me looked, to all intents and purposes, like the considerably more expensive Nike ones, and would doubtless fulfil many of the same functions. But I grasped instinctively that they would not have the same effect. I argued vehemently that I needed the latter.

To a nineties kid, Acqua di Gio was the height of sophistication

Looking back, it’s ironic how much great stuff I actually owned that I didn’t appreciate at the time, especially sportswear. In the social pecking order, I was very much a member of the geek squad, so I was acutely sensitive of anything that could be construed as an ‘anorak’.

Concerned by the image it perpetuated, I got rid of my red and blue Nike windbreaker – a hand-me-down from someone my dad worked with – at the first opportunity. I now have an expensive reissue of the exact same model.

Stage 2: Growing Pains

Puberty brought a maturing awareness of the power of clothing to express one’s personality.

Unfortunately, like most teens, I was simultaneously in the process of trying to work out what that personality was. Or rather, what I wanted it to be. This resulted in some wildly inconsistent purchases which ultimately had all the significance of a Che Guevara poster on a student bedsit wall.

Indeed, I bought a Che Guevara T-shirt, not because I sympathised with his revolutionary politics but because I thought it looked cool. I mean, dude had facial hair.

Other teenage purchases still stand out. I bought a raglan-sleeved baseball top bearing the number ‘69’, not because I was some sort of sexual pioneer (quite the opposite) but because I thought it looked cool. I wore it for a school photograph to celebrate our A-level results. When I later received a copy of the newsletter in which the picture appeared, the offending article of clothing had been photoshopped to look like ‘00’.

I bought some heavily distressed Levi’s jeans with a cinch back, partly because I thought they looked cool but mainly because the attractive female sales assistant flirted with me and my brain practically exploded with excitement.

The noughties teen starter pack: Che Guevara T-shirt, Levi’s cinch back jeans and sweatbands

This irrational self-fashioning culminated in a crisis the week before going up to uni: I lacked clothes, but was equally bereft of an identity for them to convey. In my desperation, I stumbled upon a vintage shop which sold second-hand Americana, especially college sportswear. I’d discovered a code that was authentic – and affordable.

For most of uni, this remained my bag, until I had more disposable income, and realised that trawling eBay for pit-stained ‘Trinity Trojans’ T-shirts and wearing sweatbands was preposterous (on my wrist, not my head, but still).

Stage 3: An Education

After a few years of costly trial and error, I was still no more enlightened as to what I should and shouldn’t be buying. But I had learnt at least one valuable lesson: like Samwell Tarly in the Citadel, I needed to study.

I’d always been an avid reader of magazines, and they had already begun to exercise a hold over my tastes – to the extent that I could even call them ‘my’ tastes, when they were adopted wholesale from someone else. As a teen, I’d bought L’Eau d’Issey by Issey Miyake not because of the way it smelled, but because it had won a Grooming Award in FHM (RIP).

At university, this process intensified. Putting my academic propensity to more productive use, I pored over glossy mags every month with no less fervour than the tomes I was supposed to be reading for my literature degree. If pieces were recommended by a publication, I figured, then they were beyond reproach. They’d been sanctified by an editor who was Mage-level in menswear, a taste-Maester. They were anointed, legit. I couldn’t go wrong.

And I wasn’t wrong – well, not totally. The recommendations were all valid, in isolation. But by weaving together the verdicts of different titles and editors I created some patchwork quilt of a wardrobe that would never become a coherent whole. Much less one that made sense for me.

“If pieces were recommended by a publication, I figured, then they were beyond reproach”

Which was ironic, given that I did my dissertation on the novel American Psycho – specifically, how the upshot of consumer culture is to erode individuality. Patrick Bateman is not a suave arbiter of style: he’s a composite of Giorgio Armani, Ralph Lauren and Allen Edmonds, a cipher who recycles the opinions he is fed in magazines. Even more ironically, I went on to work in those magazines. Clearly, I only learnt so much.

Along the way, I oscillated wildly from trend to trend: I was swept along on the nu-rave wave, buoyed by a purple American Apparel hoody and a Cassette Playa x Uniqlo T-shirt; then I discovered Mad Men and the joys of suits, pocket squares and tie bars; before reverse-ferreting again and investing heavily in sweatpants as athleisure limbered up.

Stage 4: Consolidation

Each new year I become more circumspect in my purchasing. I still feel the pull of a seasonal hero piece – a Palace drop or a H&M designer collaboration – but like an Ikea instruction book, I’m much more about building a wardrobe. Perhaps because I’m also at the stage of life where I build a lot more Ikea wardrobes.

Either way, I’m more concerned with plugging gaps than trying to play trend Whack-A-Mole. I try to address ‘needs’ rather than ‘wants’. And to prevent me from buying things that don’t work with other things that I own, I’ve instituted a few rules.

One: I only buy things in navy, grey, olive, burgundy, camel and, occasionally, black. (It washes me out a bit – one benefit of experience is learning not to fight what nature has given you.)

Two: all my accessories – bags, belts, most of my trainers – are black, not brown (too many shades).

Three: all my metals – watch, zips, buckles, wedding ring – are silver.

Four: I only buy grey and navy socks because trying to coordinate them with my outfit on a daily basis was consuming way too much mental bandwidth. I also own 14 pairs of identical grey underwear because I don’t want to think about that ever.

Yes, I am a fun guy.

It’s important to formulate your own style rules – such as only buying grey or navy socks

I’d like to think that I’ve formulated my own tastes. OK, so they’re probably someone else’s tastes that have been imposed upon me somewhere along the line, by some sumptuary intermediary who has subconsciously incepted me. But the point stands: I’ve established a formula for what I like and what I don’t, and I’m not going to be deviated from that. Even though I still devour magazines, and now websites, I’ve learnt to appreciate a piece for itself – yet know that it would never work on me.

It helps that I’m slightly more self-assured, and slightly less desperate to impress. At the most recent London Collections: Men, I wore plain Uniqlo supima cotton T-shirts three days out of four. A few years ago I would have gone on a panic-buying shopping spree for some ‘statement’ items. Basic? Maybe. And I did change my jacket every day. But I no longer need clothes to express my personality. Or replace it.

Stage 5: The Long Game

I’m now entering the last stage, the final boss of wardrobe-building: Father Time.

Part of the reason that I’m able to resist joining the queue outside Supreme is that I ask myself whether I’m really going to want to wear it 10 years from now. It’s possible that in a decade or so, there’ll be a generation of forty- or fifty-something guys wearing streetwear and not looking like overgrown fuccbois. (There are some around now.) But I may not be one of them. And I can’t afford to bet on something that isn’t going to pay off.

The reason: although my income has risen, my purchasing power is about to be curtailed, possibly permanently, by the arrival of my first child. So there’s no more margin for error. If I commit to buying something, it needs to work. And it needs to last.

Are we going to see a generation of fifty-something guys wearing streetwear?

I’ve moved away from visible logos towards plain clothes and brands that don’t openly advertise themselves (unless you know, in which case you know). I also gravitate towards archetypal garments – the biker, the bomber – and authentic expressions of them in lieu of marked-up designer takes. Why mortgage myself to the hilt for a Balmain biker or Fear of God bomber when I can buy Schott or Alpha Industries? There’s nothing wrong with the former, but I don’t have money to burn.

A buddy of mine used to use this expression for pieces he was grailing: ‘the one true’, as in ‘the one true pair of raw jeans’, the Platonic ideal of that particular piece, the one you saw in your mind but all too rarely when you went hunting. Back then, as aspiring swag lords, it was a source of near-constant frustration, but now I employ it as a shit-test.

If it’s the ‘one true’ version – a just-right piece that I totally love, is going to slot seamlessly into my wardrobe, bolster it and remain there for the foreseeable – then I’ll snap it up. But if not, then I’ll leave it, thanks. No more impulse buys. I’d rather wait – until the next drop, season, year, whenever. After all, I’ve got time.