There is an interesting dynamic that happens as you ramble along your menswear journey, one I don’t think we’ve talked about before. That is, as you build up a wardrobe of good clothes, you gradually get to a point where you buy less – or should do. 

At the beginning, there’s a blank canvas. Whether you’re putting together a whole new style or just levelling up the quality level, there’s quite a lot of shopping (budget dependent) and a one-in-one-out system is realistic, as each new piece has replaces another.

But at some point, this highly effective wardrobe of quality clothing begins to feel a little full. You have most of the bases covered, and while there will still be things on the wish list, realistically these are unusual, exceptional, and there aren’t many of them. 

It’s hard to recognise this and react responsibly. If we like clothes we normally like shopping, or at least the deep-dive research, analysing and agonising, discussing and comparing and even spreadsheeting, which can pass for shopping these days. 

It’s at this point that it’s tempting to follow trends – because each represents the excitement of something new, a new idea and a new purchase. What we should probably be doing is honing this way of dressing that we’ve now found suits us, our taste and our place in the world. 

It is one of the ironies of dressing well that the better you do it, the less (over time) that you often buy. 

I was reflecting on this earlier this year as I was considering the purchase of a leather jacket. 

Now, this can be one of the worst menswear decisions to agonise over, as the comedian Mary Beth Barone puts very well. For guys it’s such a question of identity, of who they are – are you the kind of guy who wears a Perfecto, an A-2, a Highwayman or (most likely) nothing more dangerous than a suede Valstarino.

Fortunately for me, I’ve already owned and worn most of those, and I have a decent idea of what works. I was looking for a new one not because I wanted a new style, but because my old ones were just too small. As we’ve discussed in detail in regards to shirts, the combination of changing tastes and changing body shape has forced me to size up in many things.

I considered a lot of options for my new jacket. Like everyone else, I love the idea of horsehide but I know I won’t wear it in for a long time (I wear too much tailoring day to day). I love the idea of a vintage leather jacket, but something in my size and a simple, wearable style is very rare. Pre-owned is usually best, and at one point I had 43 leather jackets on my eBay watchlist. Plus 17 on Vinted and 5 on Vestiaire Collective. 

But after about four months of (admittedly very enjoyable) saving and analysing, I realised that what I wanted I actually already had – a USAAF jacket from Chapal. 

The problem was that my existing one was way too small. It might have actually been small when I first commissioned it, back in 2015 (pictured above). The fact that that’s 10 years ago does make me feel slightly better about this. 

Back then I was skinnier and I didn’t feel any clothes were slim enough for me, so when I had the option to pick the skinniness, I often went too far. The made-to-measure process at Chapal gave me that choice, and I that’s what I did. 

It’s no coincidence that when I wrote about how the jacket had aged – after a few years – I was pictured only wearing a knitted T-shirt underneath. A chunky sweater would have been too tight. 

In those pictures the shoulders and back don’t look too bad, mostly because of the style of the jacket with its big back pleats. But the waist is tight and it’s short – too short to wear with anything but real highest-waisted trousers. 

As I reflected on in that article, however, I absolutely loved wearing it (more so without the mouton collar) and over the years it had really proved its value. It had also proved to be easier to wear the more beaten-up it was, and the more casual things it was worn with. 

So I went to see Chapal again, and I ordered the same thing. Last time, I had ordered a made-to-measure product with the chest of a medium size, and the waist of a small. This time, I just bought a large. 

It was very expensive. The first time I bought the jacket, 10 years ago, it was £2700. When I covered it again, it was £4000. Today it costs £5250. This is partially the kind of inflation we’ve seen everywhere in recent years with luxury goods, and I know from personal experience how much of that is raw materials, labour and related costs. (In fact it occurs to me that an article running through all that might be enlightening.) 

But the cost of the Chapal was still a lot, and I would have probably thought again were it not for the fact that I had had so many years of enjoying the jacket, and know what I was getting.  

That decision was probably one of the most boring bits of shopping I’ve ever done. But as we ramble along this menswear journey, perhaps clothes shopping should get less exciting – replaced with the satisfaction of wearing those good clothes instead, and making less frequent, better informed decisions like this one.

(By the way, I also sold my old jacket, and so found a good home for a beautifully worn-in piece that I only wish I could have had access to, 10 years ago.)

There’s a lot not included here on the jacket and the maker. For more on Chapal, see original article here. For more on why I like the jacket so much, see the ageing article here.