How my style has changed over 15 years

Wednesday, September 20th 2023
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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:

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Very interesting, Simon. Would you agree that “developing identity” in your case means more conformity? Because what you describe is avoiding all things that would make you stand out of the crowd (ties, hats, pocket squares, colours). And isn’t that an atypical development? Don’t people typically care less what others might think when they get older and are more at ease with themselves?
With interest in your further journey,


To emphasize Simon’s point, the younger man’s showiness is a product of his desire to draw attention from others. Whereas the older man is so comfortable with himself that he’s more eager to blend in. The older man is interesting in many other ways (family, faith, career, etc…) so isn’t compelled to shout to the world via his wardrobe.


This was certainly true for me. In my 20’s the whole point of showiness was to attract attention in a crowded bar. In my 40’s I’m more fond of a quiet pint in my local pub and all of that showiness is superfluous. I still want to dress well, but my context has changed, my style is more subtle.


Hey Simon,

Of the jeans/chinos in the, let’s say, off white to light beige range of colours (I know that’s a wide range), what single shade/colour would you deem the most versatile? And would you go chino or denim?

I only have tailored cream trousers but would like to add one pair of either denim or chino pants to my wardrobe that could go with a tailored jacket or knitwear.


JJ Katz

I had the same thought as yours, ‘Manuel’.
It’s very interesting to see how different people develop in their journey.
For some, it’s more individualistic/demonstrative, for others more low-key


Very interesting insight. But is it really the case that you wear less cream/white/ecru trousers? Looking at the more recent photos in the lookbook on your homepage, you seem to wear such trousers quite often, e.g. white/ecru jeans, Rubato’s cream officer chinos, casual white linen pants, cream Whitcomb & Shaftesbury Irish linen pants, Drake’s ecru jeans.

And indeed, why wouldn’t you. I wear cream colored pants (jeans, chinos, Irish linen, informal Italian linen) quite often. They seem so versatile to me because they go very well with almost any top color (navy, gray, brown, dark beige, green, and to a lesser extent even tonal with cream) and don’t seem very flashy to me. The only trouser colour that beats them in versatility is mid-grey.


Maybe I’m wrong but it seems to me that your change in disposition towards cream tailored trousers happened just recently. Quite abrupt for someone who was already well into their “sartorial journey” as they call it. “This feels like me” article was published only 19 months ago ( it was a great outfit! ). Cynic in me would ask if you’re undergoing an identity crisis or are just subconsciously pressured by need for fresh content. To be clear I do believe your tastes have changed naturally due to having open mind, being curious and experimenting.

I don’t want to be critical but you are in a very privileged position as style influencer and authority figure in this relatively conservative and slow changing menswear space where trust is built slowly and lost fast. Obviously that doesn’t mean you should be dishonest or be shackled to your past views. Nor does it mean you shouldn’t be able to evolve personally but I feel that in this particular case a little more thought should be put into how you affect people who you have inspired.


I can remember an article from years ago where you said something to the effect of “I wish I lived in a time where more people wore cream trousers”. So I’ve always assumed you had reservations about how showy they are and therefore not surprised that you no longer wear those at the creamier end of the spectrum.


Just to offer an alternative perspective, I own 2 pairs of cream/ecru trousers and I guess you could consider them showy or flashy but even more than that just quite situational and lifestyle dependent. Think track shorts, these will seem odd in a lot of situations but on track and while doing sporting activities they are perfect. 

For example I’d wear mine when meeting a friend for stroll in a park, having a lunch/dinner with female companion in a nice but relaxed restaurant during weekend or visiting an art gallery. I wouldn’t wear them to visit a dentist, pick up kids from school, shop groceries or when meeting new clients ( although you easily could in a right field ).

To sum it up, I wear mine on average about once a week, usually during leisure activities on dry and sunny autumn and winter days. I find they set a good mood and there are certainly people who can appreciate that, you just have to be considerate of the occasion and your lifestyle reality.


Interesting, I would never think of an ecru trouser as flashy (at least during the day). It’s all personal, of course.

Really enjoyed the article and I agree you’ve really found your stride in recent years.


What`s your thought on cream/white heavy brushed cotton “dress trousers” (sans pleats)?


I really like wearing cream/beige cord trousers. Maybe that’d be a more casual alternative to moleskins?

Lindsay McKee

This is an astonishing article Simon..just great!
Now,have I learned anything since discovering Permanent Style?


1. Mute the colours…with exceptions. My knitwear didn’t match and some of my pieces are purple and bright blues.
I’m now acquiring navy,greys, cream, dark brown, black, charcoal,dark green etc, and gradually relegating some of my knitwear.
Look at Drapers Ascot for trousers.
I actually confused a very cold light brown for grey!!!

2. I wear no watch…only on occasion. I have my mobile phone.

3. I wear a tie..I’ve cleared out a load of them. At a wedding reception,I noticed a “weight” as it were hanging from my neck.I had to remove it. I like bow ties for less weight or usually wear no ties.

4. I wear a long sleeve polo shirt mostly as it is less restrictive and more comfortable…. usually Smedley or Lacoste. Short sleeve in Summer.

5.Shoes. I appreciate good shoes. Dark browns rather than black.
Probably a LAZYMAN shoe on advice from Gaziano and Girling.I do suffer from Asthma unfortunately.

6.Trouser belts. I’ve already discussed my view in a previous thread. I struggle here. I’m confident and comfortable still with belts.

7. I have a suit but prefer separate trousers and jackets and mixing and matching and enjoying them!

There may be others, but here’s a few of my options.


Now this is a fun idea, what have readers learnt from permanent style? I wonder if people self-classified as to where they thought they were on the “style” journey when they came across the blog how much consistency in answers there would be? I suspect a lot!



There’s an aspect of your style that’s always clashed with my own understanding of the often mentioned rules of menswear, that of wearing darker rather than brighter trousers than jackets. I avoid darker trousers myself and find it an easy way to achieve balance in the overall outfit. As such, I’m often fond of cream and beige trousers, although perhaps the cultural assumptions of showiness you mention are not as prevalent in Sweden, where they’re quite ubiquitous.

In any case, I recognize that with more knowledge and experience, or perhaps style, such rules can be put aside with more ease. You’ve demonstrated this repeatedly, and mention darker trousers multiple times in this article. Yet I can’t quite do away with a sensation that most of those looks would still look better with a lighter shade of trouser, to balance a darker jacket and lighter shirt.

Do you have any reflections regarding this? Perhaps they can be of help to me in finally breaking free of this mould myself. If nothing else, I imagine darker trousers would be more forgiving in our northern climate of rain and snow…

All the best.


For what it’s worth, I have long found that rule or convention to be nonsense. The only guideline I follow is that the trousers should contrast with the jacket. I find some of my most worn combinations are dark grey trousers and a mid-light coloured jacket (grey, brown, stone, oatmeal, and even burgundy). It’s different to how most people wear sport coats but not in a particularly showy way, and like Simon alludes to it looks more modern to me even though it’s nothing new (there are plenty of black and white photos and old films showing men with darker trousers and lighter jackets).

Although I’m confident wearing this, I would be interested to read a piece on this by Simon or Manish.


Thanks Simon – the two photos side by side show the development. Glad the explanation is more straightforward than one of the slightly harsh armchair psychologists came up with last week 😂

Have you always used the same photography team since starting PS?


Nice Simon, just one thing first, tight suits have stuck around way too long… is this half the problem now? Wearing a tight suit, tight everything, is just the norm? I attended a wedding a year or so ago, men of all ages, everyone’s suit too tight (probably mine included honestly), numerous funerals over the past number of years, yep you guessed it. I go outside, everyone’s jeans far too tight… when is it going to end Lord have mercy? I thought it would have died a death long ago… rant over.

I have to say, you’re looking better than you ever did. Darker colours, more black around the edges and yes without a doubt, the fuller cuts are where it’s at. You’ve included one of my favourite photo’s of you above, in the suede Himel Shinki jacket.

Eric Twardzik

Pity the pocket square: coming of age in the Mad Men era I was led to believe they would be an essential, and for a long time they were the only thing I could afford from Drake’s. I bought a pile of them in beautiful designs that sit in my dresser drawer drawing dust: now and then a white Irish linen one comes out to play.

Overall, all those “fussy” accessories I obsessed over in my youth – pocket squares, tie bars, and god help us, collar pins – have come to look like unneeded distractions.


I have a pocket square collection too. I’m going to find a place to display them one day. I will ware one of them, once, at some point—I have an outfit in mind, but it’s heavily dependent on both lighting and weather lining up in a particular way. Except for that… yeah, they’re just pretty collectibles.

Peter K

I still wear a pocket square but I only have 4 now. I find they add interest to more typical outfits (e.g. navy blazer, white shirt) that would otherwise be rather bland.


I only wear pocket squares with suit and tie these days. My collection is far too large.


Hi Simon, this is a great article I must say. I am noticing year by year that regardless of the shape or cut (Neapolitan) of the jacket, it makes me stand out from the crowd, especially during spring, summer and even sometimes in Mayfair. Obviously, there are still many people who wear navy suits but I feel like it’s getting rarer to spot many people wearing jackets and trousers.

On another note, may I ask what outerwear you usually wear in the current weather in London? I find it pretty tricky to choose one, and linen no longer feels quite appropriate when it gets colder in the evening, and tweed seems a bit too much in the afternoon.

Many thanks,

Peter Hall

One thing which has directly impacted on my style is the desire to use less water and limit dry cleaning .So, more casual,more work wear. Much more rugged texture.

Five years ago,I was having 6-7 shirts dry-cleaned weekly and am now reduced to two washes per week(NO KIDS). and no dry cleaning.

I definitely concentrate on the overall style. I’ve lost much of the fine detail -ties,squares,watches,expensive aftershave,stiching -I think this may be an age related desire to have less clutter(or patience ),but cost saving has certainly had an impact.


Very nice article, Simon. I’d be interested in hearing more about what you’ve learned from designing or co-designing your PS collaboration pieces. For example: has working with Private White given you more insights into what makes great outerwear and how to find a balance between practical performance and style? Has it taught you anything about what details require or deserve more attention? Has this experience helped you develop your personal style? I can only imagine that having the opportunity to experiment with all those design tweaks on jackets, coats, knitwear, etc. would have an impact. Cheers!

John K

Hi Simon,

Your comment on looking better is interesting to me. Not to blow smoke up your behind (I’m sure you get a fair bit of that already), but you do look significantly better looking these days. I’m sure that’s why you put the old photo at that fitting next to the more recent photo in the brown jacket. I think the kids call that a ‘glow up’.

I would presume your improved appearance is down to you knowing what clothes suit you, how to cut your hair/beard to suit your face, feeling settled and confident in who you are, perhaps looking after yourself physically a little more. These seem to be things that occur to men in their 30s and beyond. These are all good things and it’s nice to see this with you from afar.

My question (if there is one), is how much more important is your appearance to you these days? And are there any downsides to this? I find it interesting how the change you’ve experienced with the attention from this site and Instagram impacts someone’s mindset. I’m not sure the human brain was designed to deal with all that. Is there a fine line between taking care of and being into your clothes/appearance (positive) and being vain and taking too much enjoyment from the validation of others (negative)? How does someone in your position manage that?

Apologies for the rambling message. Just some thoughts. I believe I read on a previous post that you’ll soon be writing an article on vanity, perhaps you’ll cover some of the above there.

Hugh de Montfort

I think it inevitable that age and experience have a bearing on how one feels about dressing.
When you were starting out, writing mostly about suits, you were very dogmatic and “anal” about technical details, finishing and handwork. It was almost as if you were politely dismissive of those whose products didn’t come up to your “standards”.
Gradually, you have come round to the point where you consider things more broadly and stress less about individual details. What seems to matter more to you today is how something makes you feel when you wear it (if only to the extent that it doesn’t make you “cross” in some way), and how an outfit comes together in a pleasing way.
My sense is that you have, over time, “learnt” how to dress well, as indeed we all do. One caveat, though, is that because you are doing this for your living, you zoom around in a much larger spectrum of styles. looks and origins than the average guy, and so it is harder to understand what you really are when you are being you.
Having spent my working life in bespoke suits of one style or another, retirement gave me an opportunity to explore a whole spectrum of dressing in a more casual way and I found the opportunity to experiment and be creative an exciting one.
Vintage and the like is not my cup of tea; I’d compare my dress style as closer to Boyer than Bowie, but it’s always interesting to see what others wear.
By the way, if you haven’t seen one of the many Chanel exhibitions doing the rounds, do go and have a look. Even though her styles are now decades old, you can clearly see how they have evolved into much of women’s “fashion” today.


I looked at your “unusual tailoring,” article and spent a minute trying to understand why it was so unusual before I realized that the suit was green. And it’s everything.


Hi Simon, An interesting read. I did smile about the reference standard deviation to the mean, which shows a possible through-back to your previous career!
It’s a great description. Since I retired 6+ years ago I found the mean moved at first and then the deviation to it became smaller as my lifestyle changed (e.g more time with grandchildren and less need for formal wear plus the discovery of The Real McCoys thanks to your good self). Still with a few outliers- some more successful than others! All the best.


Great article Simon. Love that suede jacket! One note – a woman sued Tyler recently, alleging that he sexually assaulted and battered her when she was a minor in the 1970s. Might be wise to take down his photo here given these allegations.


Quite correct.


The challenge, as I see it, is the ability to express yourself in an increasingly casual world. I’m in finance and work in California. My co-workers wear jeans and a casual shirt.
The risk is sticking out too much. Indulging in my passion for dressing well without being a unicorn.
This article very much resonates with me.


Thank you for this post, Simon. I discovered PS just a few months ago, and I was detecting some of these differences between older posts and newer ones, but it’s so helpful as a new reader to have your own retrospective on your progression.

You are indeed looking better these days, and your development a great inspiration to those of us just starting out.


William B. Schwartz III

I would be grateful if you would let us know where the mid-brown leather is from that is in the photo
Of you wearing cream trousers.

With thanks,

Bill Schwartz


In my (very personal) view you are still too cautious and moderate on colours. Some red, purple, green or burgundy on an occasional basis would give a moderate twist without being flashy.


Thanks for a great and insightful text. Personally, for my self and when I look at the changeling in style that’s happen the last years. It’s the shoes, bespoke shoes or expensive ones (not EG) very often looks like beautiful sculptures with fantastic craftsmanship and patina or unfortunately well made kitsch. I often find the shoe nerds and bespoke shoe enthusiast a bit odd, they are often just giving the shoes all the attention.. and the rest of the outfit is just on vacation. Of course there is exceptions, age, personality and so on. Not meant to say it in a rude way to any reader. For myself and I think for many others it’s mostly, loafers, dessert boots, sneakers, that’s are in use. I haven’t use a laced shoe, oxford or derby in three years…I saved my last pair of black Oxford for funerals.
The strange thing is that black oxford, derbys, brogues, looks great on my wife and other women…they look just elegant not overdressed or too formal. Maybe its just work better with chunky knits, big skirts, slouchy trousers.. more fashion less anachronistic.
I made a couple of heavy, navy chalk-stripe suits when I was living in London 12 years ago, luckily I made two pair of the pants, always (not sure if that’s common now) and waist coats..never used them just to much cosplay, huh. Anyway the pants is fantastic and in use!


You seem to wear casual clothing (e.g. M65 jackets, jeans, t-shirts, baseball caps etc) from Japanese and fashion brands more now than you have ever done. It also appears that you don’t often wear your British bespoke tailoring (e.g. Huntsman, Gieves & Hawkes, Chittleborough & Morgan, Michael Brown) now. That’s disappointing because I much prefer those suits, jackets and coats to those from Italian tailors. Perhaps you could comment on my perceptions.


I would love a article about English v Neapolitan (Italian, thinking about Florence, Rome and Milan) tailoring!

Peter Bodach-Söderström

Very interesting reflections. But isn’t it also a question of changing sides? You were in the corporate world and now you’re one of the culture elite (sort of), two groups with different codes altogether.

Peter Bodach-Söderström

That actually makes sense. Thank you for taking the time to answer.


I have started limiting purchasing men’s clothing. Not just because of less formality, but I started thinking about what I will do with it all as I age. I can’t take it with me. Also, what do you do with all this clothing you bought over the years and don’t use? Sell?

Peter Z

Permanent style has really opened me up and developed my style the past few years and somehow I developed breadth of style.

The other day I had a really really long flight (when traveling in Europe I usually do so in loafers, blazer and trousers) so it was a Real McCoys hoodie and sweatpants with tracksmith sneakers. And then I had my Michael Browne suit, D’avino shirts and Nicholas Templeman black cap toe oxfords for the MET and the night events, and my Ironheart jeans and Real McCoys’ tees for the days.

This is what I love about PS that it showed me quality in such a variety of styles but also opened me up as I used to only wear jeans and crewnecks casually and blue suits for work. Today I absolutely love the Real McCoys, Merz B Schwanen. These are probably my most favorite brands even when compared to SR tailoring.

So thank you Simon

Panagiotis Papakanellos

Great article Simon, most inspiring and interesting! Pls correct me if I’m wrong, but I can recall that you favoured off-white/cream triusers. This has been changed a little, right? Why? Is it for practical reasons or you have found out that are not that versatile?


I particularly liked this outfit from Pitti one year ago with the cream linen trousers. I guess at an event like Pitti this is not showy at all. But also outside of Pitti I think this would still make a very nice and not loud summer evening outfit.


Would you instead wear the more oatmeal colored trousers you linked above with your Dege & Skinner jacket today, or do you find yourself pairing that jacket with another shade of trousers? I’m curious whether “showy” is just about the amount of yellow or also refers to the amount of contrast between jacket and trousers in this example.


Would you still endorse the Zegna “denim” twill from Pommella?


I am sorry to be annoying about this cream-color-theme. But I am confused. You say less creamy is easier for you to wear now, but in the article I linked above with the cream W&S trousers you said that “I also find linen that’s a little creamier is easier to wear, like the Holland & Sherry one I used for my Jean-Manuel Moreau suit.”. Could you please try to clarify? Thank you!


Great article.
Reading it reminded me of my own evolution albeit mine occurred at a younger age.
My interest in the sartorial started when I was about twelve and was driven by an interest in cinema and music. It was the ‘60s so the days were halcyon. That said, my evolution was the same insomuch that my early years I was preoccupied by an interest in some elements rather than the totality and it wasn’t until ‘69 when I saw McQueen in ‘Bullitt’ that the penny really dropped.
Here was I guy who eschewed all the trivia of the time : No flared trousers or loons. No clunky ID bracelet or platform shoes. No blow dried bouffant hair. No Tommy Nutter tailoring. All of the trappings of the era were studiously ignored but yet here was a guy that just looked completely right in every circumstance. He was understated but was achingly cool and would be equally at home in a rock concert or a politicians office.
Of course when you deconstructed the look you saw it wasn’t as easy as all that. He had a killer haircut. His wardrobe was seamlessly matched and the choices made for each environment were pitch perfect. Nonetheless it was the totality of the look that grabbed me and I left the cinema knowing that this was going to be the actioned standard and I went on to plough that furrow and I certainly can’t see me deviating from it now.
It seams to me that you’ve learnt that it’s the totality that really matters. If so your ‘Bullitt’ moment has truly arrived. You won’t change much going forward.

Hendy Drake

Really lovely article Simon. I certainly agree that you look better now. More relaxed and “causal chic”. I do wonder, though, if evolution is just a byword for cyclical and we’ll all look back in ten years and comment on how ridiculous we all looked now! I hope not and feel like we may have landed on a more timeless approach when compared to the slightly costumy approach to dressing we all adopted in the noughties. I guess only time will tell and may as well enjoy our clobber in the meantime!



I started investing heavily in quality menswear around 2012 (bought my first EG Dover that year, and started bespoke with Huntsman around 2016). I’ve held admiration for styles depicted in Ralph Lauren ads before that as well.

Just recently, I’ve started to realize the reason why many of my items amassed over the years haven’t gotten as much wear as I anticipated. They are stylish of course (Florentine and Savile Row suits, overcoats and tweed jackets, West End bespoke oxfords, etc.), but the garments and accessories I’ve bought RTW and bespoke were heavily influenced by what I wanted to look in my head, and almost as frequently, how rakish acquaintances defined ‘style’. The items were purchased individually, and certainly they had character, but I never really considered how I would wear them with my existing wardrobe, let alone if they were appropriate to my lifestyle and geography. I’m trying to rectify that situation now, buying less and thinking specifically how I would eventually wear new clothes if I were to purchase them.

This article was timely, at least for me. Instead of attending trunk shows without much thought and hastily forcing myself to order an expensive garment that might not get much wear, I’m more selective because I think I have a much better understanding of what I like and what’s worth the investment. Your site has been extremely helpful in the education process.



I am long retired and used now to wearing a variety of relaxed, casual outfits.
However, I recently had to attend a commercial tribunal in Geneva as an expert witness.
Dress code for such an event is very strict, and I was obliged to wear a suit, shirt and tie.
My goodness it felt good!


I’ve not really enjoyed the trend towards increasingly casual wear on PS. There is something special about putting on a suit and a tie that cannot be matched by any casual wear. Having said that, I am of course also privy to the fact that dress codes and dress expectations are being casualized, perhaps inexorably so (who knows how far this can go!). Certainly, from an aesthetics point of view this is a great loss, just as for example expectations of the aesthetics of architecture are far less than they used to be. But, alas, we do live in a society and unless one is particularily ignorant to what others think of them we do have to conform within reason.


Very well put dear Simon! Your writing and analysis are what always has put you apart. The willingness to experiment for all of us makes for a treasure trove of “sartorial” knowledge.

Jeppe holst

Wow Simon
This is one of the best articles you have ever written. In my opnion your personal journey to find your style has been the most interesting part of Permanent Style.
All the best
Jeppe Holst


Very comforting to hear your burned all that money once too. I’m at the beginning of the journey and just bought my most expensive trousers. Hopefully they’re worth it


Hi Simon,
At the begeining of PS, I got the impression that you didn’t like tassel loafers. And then later on you started wearing them quite consistently. From my perspective, this has been a dramatic change.
Srangely enough, it’s actually hard to pin down your personal style solely from your posts on PS. For sure, from time to time, one would say “oh, yes, I could incorporate this or that outfit into my wardrobe”. As a whole, however, it would be hard to do so.
Over the same years, which items in their wardrobes readers have sought to improve, to upgrade? and why? which ones have they ditched, and why? Are these behaviors anyhow related to the lifestyles within their respective countries, regions and cultural settings?
Are there depictable patterns in those behaviors that would make certain changes quite predictable according to those environments?
Which roles play cultural events, whether local or national, in those apparently individual processes?
Isn’t the so-called trend toward casual limited to Europe & the US?


A very self-aware article Simon. Although my style is a bit different to yours, I have found it has gone through a similar evolution, so I can relate to most of this. I used to wear mostly vintage clothes from the 1930s-50s, whereas now with the exception of a few pieces I mostly wear modern classically styled clothes. Like you I try to avoid looking flashy. The bit I relate to the most is dressing “more me”. I used to want to dress like the black and white era actors that first got me interested in clothes, whereas now I just want to dress as myself, someone who has their own sense of style but one that’s subtle enough that it would not stand out in a crowd.

Aaron L

I love the little notes about using two credit cards, etc, to pay for shoes. It makes me think of one of your earlier articles about building a wardrobe in a budget and the flak some people gave you about how much you suggested shoes each year. I used to rent out all the rooms in my house and sleep under the table to afford shoes, etc – so I thought your recommendations seemed reasonable. It made me smile to read that you were making similar trade offs in your youth. I don’t think I’ve expressed myself well here, but hopefully it makes some sense.


Good afternoon..we all change 2 a certain from memory u were in Harrods talking about various wore braces/ u do not..what year was that?? My guess 2011 or 2013..peace

David Lilienfeld

How old were you before you were open to wearing a Donegal tweed jacket?

Tommy Mack

Great article. I think my own style, ahem, evolution aligns with all the main points you’ve made. Maybe part of that is growing older (I think we’re about the same age) and having kids but probably the influence that Permanent Style has had on my own wardrobe!

Henrik Hjerl

Very interesting indeed!

Henrik Hjerl

Very interesting reflection indeed


Hi Simon, 
I had a more specific question. It’s about the way suits fit me and I can’t put my finger on it. If I look at your pictures, your suits fit very well around the shoulders. From the side of your neck to your shoulder, there’s always that downwards line. Not very steep, but a subtle downwards line which looks very elegant and masculine.
With most of my suits, it’s a horizontal line which in my opinion doesn’t look as good. Most people have this as I look around at formally dressed people. However; I have one jacket (not a very expensive one) which also gives me this downwards angle from neck to shoulder. I look fantastic in it. I dont understand why only this jacket fits me this way and the others don’t.
I’ve enclosed two pictures (second one in next comment). One has the downwards line like all your jackets have. The other one lies horizontal on my clavicle-shoulder, like most of my jackets. I’m 5’9 and about 158 lbs (72kg) and fit.
Do you have an opinion on this? Thanks in advance. Btw I just ordered the blue Oxford shirt from the PS site!
Best regards,


Here’s the second one;


Simon makes the tan leather bag shown above?


Simon whose traveling bag is shown in the photo in the above article?


Hello Simon,
As you mention, there is a general decrease in formality, which is even more marked on the continent and in some industries.
As such, how do you feel about worsted suit for people not working in banks / insurances and living outside UK / Scandinavia ? Would you say having one in grey or navy worsted wool is still making sense for those persons, or would they be better served with more casual fabrics / colors, such as a navy donegal with specks of other colors or alternatively a much lighter blue, as the simple fact of wearing a suit or even just a jacket risk making them stand out?


Hello Simon,

You wrote that navy trousers would look more subtle than the cream trousers, which I agree with. However, doesn’t that make it difficult to pair the charcoal donegal jacket with other odd trouser colors? Are there options besides navy?

And what navy material would go with this jacket?