A few readers have asked recently how my style has changed in the time of writing PS. Here’s an attempt to summarise how I see it today, with a good many links to other articles to flesh out the points. 

First, there are a few different causes, which I think it’s worth setting out at the start as they often get confused. 

1. Just learning to dress better. In the sense of more flattering, being more appropriate, and liking what I wear more. Also, perhaps inevitably, and interestingly, objectively dressing better. Defined as: other people think so (friends, readers, strangers) 
2. The world changing. A steady reduction in formality, exacerbated by Covid. Then shorter cycles, lasting perhaps 10-20 years, which affect things like suit fits (bigger), more/less streetwear (now peaked, hopefully), colour palettes (black, tonal). 
3. My circumstances changing. Getting older, having kids, kids growing up, changing jobs, and having more or less disposable income (goes up and down more than you think – peaks before you have kids, perhaps, and then again 20 years later).

Now, below, five ways in which I think my style has changed (it always seems to come out as five).

Less fussy; or, less about the object

When I think back to how I used to dress, the first thing that strikes me is how fussy or showy individual items were. 

I used to get obsessed with shiny shoes – as a friend puts it ‘spicy’ designs. I spent nearly all of my year-end £1000 bonus on a pair of Berluti lace-ups; I used two credit cards to buy my first pair of Corthay. It wasn’t just shoes – as I related in my piece on my history with Anderson & Sheppard, my first commissions were a Prince-of-Wales suit (largely unwearable in the office), a royal-blue flannel DB (worse) and some cream gabardine trousers (impossible smart). 

The biggest change I’ve gone through in the past 15 years is understanding that style is about the whole, not the individual item. It’s about how you put it together, and how you wear it. 

Less showy in some ways, more experimental in others

Now, a more subtle point is whether I’ve become more or less ‘showy’ – wearing things that stand out more. 

Given I no longer wear those spicier shoes, and hardly any cream trousers (I don’t think I would ever say a cream-linen suit is a ‘menswear staple’ as a reader put it – at least not in this age) surely I’m dressing in a less showy manner? 

Perhaps. When I look back at outfits like the one above, I immediately want to simplify it (remove pocket square, remove cardigan) or pick subtler colours (navy trousers, dark-brown shoes). It’s just too much. 

And yet, this all-black jacket/jeans outfit is hardly an everyday look, and I feel increasingly interested in mixing things up by, for example, wearing chalkstripes as separate trousers, perhaps even a jacket. 

The difference, I think, is that this recent experimentation is done with subtler colours and textures; it’s dark browns and blacks, focused on materials and proportions. Perhaps it’s unusual but it’s not showy. And in fact the reason it probably feels experimental is that it’s pushing against classic-menswear conventions. 

Broader interests, more open-minded

This change has definitely been influenced by causes numbers 2 and 3. 

Because I no longer work in a corporate environment every day, I’m less likely to wear more business-like tailoring – fewer worsted suits, fewer navy blazers and grey trousers. I still love this simple, clean look, and still write about it. But I’m more likely to give it my own spin – eg still a white shirt and black shoes, but a brown dupioni jacket and darker brown trousers. Formal but not corporate.

As I’m also in town less often (usually three days out of five) I wear less tailoring overall, and more workwear and denim. I always wore this type of clothing but only at the weekend, and as a result I thought about it less, spent on it less. Readers will all be aware that I’ve written more about such clothing in recent years, and that’s because I’m interested in what I wear more. 

That’s also meant tailoring is more for events, often for the evening, and it can stretch its wings in that direction. More cocktail attire, more unusual tailoring that plays with making a statement.  

Bigger fits; belts not ties

Some changes are more specific, concrete and get more attention – perhaps because, as with point one, there is a natural tendency to focus on objects. 

Few pocket handkerchiefs, for example. This was always a trend anyway, one of those 10-20 year things. My father never wore a pocket square to the office, and my grandfather only ever wore a white one. Same with braces. 

Fewer ties. This is the opposite, a long-term trend, a slow death that has come with the decline in formality that’s been going on for over a century. My father grew up wearing a tie to work, wore them less as he got older, and now they’re an unfortunate rarity. 

Bigger fits. A trend like the handkerchief: suits were tight when they came back into fashion in the 2000s, and that look has stuck around too long (blame the fragmentation of the media). But more comfortable fits and drapier styles are everywhere. 

As I’ve commented before, having ‘permanent style’ is about the combination of dressing for the world around you and for yourself. It’s about changing, just not too fast or too far, and retaining your own identity along the way. Which brings us onto the last point…

Developing my identity

Everyone starts off by dressing like everyone else. It’s what inspires you. But over time, as you make little choices here and there, you start to develop a personal, deeper-rooted style. A good dresser always keeps an open mind, but their average becomes more consistent (picture a graph) and the standard deviation reduces. They settle around a mean. 

When I wrote about cold-colour clothing a few years ago, it was because I recognised this trend in myself and wanted to define it. Same with the way I keep banging on about ‘casual chic’ (also in Summer). These are ways of dressing I have honed in on, that I feel myself in and as a result am more comfortable in. 

I once attempted a definition of style as including consistency, knowledge, personality and ease. I think I’m developing more personality, and becoming more consistent and easy as a result. 

Nothing affirms this more than the informed opinions of others. When I went to see Nicoletta Caraceni in Milan this summer, for the first time in about five years, she looked me up and down in that way she has. The way that suggests she doesn’t just not suffer fools gladly, but physically beats them and throws them from the balcony. 

“Mmm, yes,” she said, before I’d even said hello. “You are looking better these days Simon.” I couldn’t resist fishing for another compliment, and asked her what she meant. “Physically better, and when I see you online, you look more like you.”

I know I’ll carry on making mistakes in the way I dress, and I’m sure I’ll look back in another five years and want to change things. But I also feel I’m getting better, more comfortable, more knowledgeable, and definitely more me. It’s been a tremendously enjoyable journey, and as Steve Tyler will tell you, life’s a journey, not a destination.

Further reading: