We’re used to saying on Permanent Style that clothes are a matter of self-expression. That you have no choice but to say something by the clothes you wear – but that’s also an opportunity to express yourself, to make active, enjoyable choices. 

This line of argument works for those who are more expressive, perhaps more artistic, and enjoy that creative exercise. But I’m not sure it appeals so much to the average reader that wants to be simply well dressed. 

So here’s a different way to look at it. 

One of the richest aspects of clothing, I’ve come to realise, is that it shows, it illustrates, how you change as a person. You wear different things at different stages in life – dating, parenthood, retirement; various jobs; activities and passions; your developing taste; caring more or less about the trends around you, which are of course themselves a factor – and this history of clothing is a history of yourself, of your personality. 

I used to say that clothing was a lot like cooking. You have to eat something just as you have to wear something, so you might as well understand and enjoy it. 

But clothing is actually much richer than that, because it changes more with your journey through life. What food you like and what you cook will evolve as well, but it’s less expressive and less personal. 

When I was 23 years old, and first getting into suits (because everyone around me wore one) I wanted things that were obviously different, that stood out. My first designer purchase was a grey Prince-of-Wales suit from Etro, and I thought it was beautiful. But it was completely inappropriate for my job. 

When I had my first suits made on Savile Row, they weren’t as lairy as that, but they were still loud. The worst was probably a rich-blue double-breasted flannel suit. I got it because Karl, the salesman, had one and looked amazing. But then he worked in a menswear shop. 

It’s easy to see this history as simply a litany of mistakes, but I think at every stage the choices revealed something about who I was at that age. It’s not that I’d buy better suits that stand out at my age now; it’s that I don’t want to stand out in that way at all. Those suits were just as personal and expressive as the Wildhearts or Pearl Jam T-shirts I wore when I was 15 years old. 

My taste has sobered – and I think improved – over time. Much of my favourite tailoring from the intervening years illustrates this, such as my grey herringbone jacket from The Anthology (below). 

But interestingly, I’ve now also found that I can dress a little more unusually than those office days, because I work in menswear. For me, that is usually nothing more than a double-breasted jacket or a western shirt, but it’s a point between the Etro and the grey herringbone, and I think it says something different about who I am.

I did another episode of Jeremy’s podcast Blamo! earlier this year, when the two of us were in Florence, and he brought up this point. 

When he started working at The Armoury in New York, many years ago now, it was at an exciting time for menswear. It felt like there was a new freedom in how ordinary men dressed, in how the average guy was permitted to think about clothes. 

“But over time that seems to have morphed into sites that obsess over stitch count on shoes, or the best value knitwear,” he said. “The point for all of us at the start was that dressing well was about enabling you to do other things in life – understanding what clothing said about you, how to use that to express who you were. It was purposeful and personal.”

For Jeremy, clothes have definitely reflected who he has been over time, and they became very invested emotionally. My favourite example is an old oxford shirt he wears with frayed collars and cuffs – plus a hole in elbow that was patched by his mum. 

There are a few other interesting things in that podcast, including how AI affects sites like PS. It makes such a difference when chatting to someone like that you know really well. 

Returning to life’s journey, I don’t think it’s as simple as saying you just wear different things at different ages because you have to, or because fashions change. There’s always a bit of agency in there (albeit far more the more you’re into clothing). 

Perhaps the clothes I wear today are kind of a reflection of two interdependent things: the fact that I understand clothes now more than I used to, so I can express myself better; and the fact that I want to appear a certain way, which has varied over the years.

So, for example, I am more comfortable today than I ever have been at appearing a little sexy – at leaving one more shirt button undone in the summer, perhaps. (I’m an Englishman remember, these are baby steps.) I wanted to appear good in the past, stylish and I guess attractive, but not really sexy in that way. 

Just as importantly, I know enough about clothing today to know the best ways to  achieve that effect, in a personal and subtle way, rather than brash and cocky. I know it’s sexier to be relaxed and comfortable in whatever the clothes are, rather than clearly trying very hard. That’s the problem with all those super-tight suits. 

Clothes are a way in which, over the past 20 years, I’ve got to know myself. And at the same time, they are a key way in which I’ve been able to express it. 

I’m sure many readers have felt the same. I’d love to hear some of them.