Honing your style

Friday, August 14th 2020
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Over the years, it’s noticeable that even the most fashionable, the most clothes-obsessed of men tend to narrow their tastes. 

It takes decades, and often involves a lot of experimentation in their 20s and 30s. But by the time they reach 40 or 50, they’ve usually honed their look to something they particularly like, that suits them, and that fits with their lifestyle. 

You can see this with men we admire on this site - Yasuto Kamoshita from United Arrows perhaps, or Mats Klingberg at Trunk (above) - as well as fashion designers, like Giorgio Armani or Ralph Lauren. 

They still play with clothes every day. They still find new things that are interesting, and will work some of them into their wardrobe. But their overall look doesn’t swing as wildly. 

Ralph still wears menswear classics and mixes them in his high/low way (with admittedly, varying levels of success); Armani wears his white T-shirt and muted tailoring. 

Kamoshita-san (below) described something similar when I spoke to him at our Japanese Symposium: “I love clothes and will always find them interesting,” he said. “But what I wear for myself is actually quite restrained - usually mixing different elements related to tailoring.” 

So he might well experiment with bright-coloured polos under a suit, or bold-pattern jackets; but he won’t suddenly switch to streetwear, or full-on Issey Miyake pleats. 

I find this interesting because I think it applies to many ‘normal’ men, particularly readers. 

So many older readers have told me - usually at events - of the different phases they went through: the workwear phase, the all-black phase, the 60s tailoring phase. Before they settled on something rather particular, and personal - and that often combined many of those elements. 

It’s perfectly natural, if you’re passionate about clothes, to be excited by things that are new. But over time you learn that you need to filter those for things that work for you. 

Those readers might find it reassuring that this is a path also trodden by the fashion industry as well. Designers often experimented when young, as well, before focusing on the black-and-white, velvet-and-denim of Tom Ford, or blue-on-blue of Noboru Kakuta. 

It’s a difference I think you could also see between Tatsuya Nakamura and Tomoyoshi Takada (above) when I interviewed them last year

Takada, being younger, experiments far more with his outfits - mixing together more styles and genres. Whereas Nakamura, from what he said, clearly has a more definite sense of what suits him. 

Physical ageing is probably also a factor as we pass 50: we may not be as slim, as athletic, or as hirsute, and can perhaps get away with less.

I’ve noticed this gradually in myself in the past five years or so. 

Although I’ve never been into high fashion, and have shied away from anything too trend-driven, I have tried everything from the most formal English tailoring, to workwear denim-and-hoodies, and Ivy madras-and-seersucker. 

I find I’m settling into not one of these three, but my own personal combination.

I wear hoodies less, preferring a crewneck sweatshirt. But I also lost the passion for high-waisted trousers, waistcoats and tie-bars a while ago. 

My sweet spot involves cashmere or tweed jackets with flannels or denim, draped suits in cotton gabardine or cord, and casual shirts - whether oxford, denim, linen or piqué. Often mixing tailoring with other genres.

This theme is something Jamie Ferguson (above) touched on in his recent piece for Permanent Style (sitting alongside James Allen - who has a particularly honed wardrobe). And it’s something I discussed with Scott Schuman, The Sartorialist, during a recent interview on Instagram

Scott remarked how much he likes wearing something approaching a uniform; how many times he has tried colour over the years, and decided it just isn’t for him; and the point he realised so many designers are the same. 

Scott was wearing a black polo under a black suit on the call (he admitted getting dressed up just for us) and said he could happily wear this all the time. His wardrobe is apparently all navy, grey and black. 

And in fact I was wearing a denim shirt, T-shirt underneath, and tweed jacket. My go-to. 

Scott includes a chapter on this tendency in his upcoming book - Man - and emphasises that, just because you dress with less variation, it doesn’t mean you stop wearing new clothes. 

They’re just more likely to work within smaller circles of your existing wardrobe. 

At the most adventurous (on the edge of that circle) for me, this might be baseball caps. I hadn’t really worn these with my other clothing until recently, but I now do it more - because the contrast with tailoring fits with how I dress. 

And an example of something less adventurous (closer to the centre of the circle) might be awning-stripe shirts, or very tonal combinations. 

This honing of your look doesn’t mean you stop being interested in fashion more generally, either. You can still appreciate it, comment on it, watch and absorb it, as an artistic pursuit. 

Designers come up with the most wildly original shapes, patterns and proportions, all while dressing conservatively themselves. 

Now, you don’t have to be quite as narrow as them, or even as elegant members of the menswear community like Klingberg or Kakuta (below). 

But I would say it’s worth considering what your style boils down to, and what you get most enjoyment out of. Particularly in these uncertain times, it might mean you end up buying less. And indeed wasting less - buying fewer things that are rarely worn. 

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Very thoughtful post, Simon. Your points on the honing of style as one ages are, I suspect, true not just for clothing but also a myriad of other interests. Information gathered, knowledge gleaned (hopefully) and an experience of how that fits into one’s own life inevitably leads to a distilled approach. The beauty however is that even as one’s framework narrows, there is the opportunity to still incorporate new items, keep things fresh and one’s own passion and curiosity kindled. A great approach for clothing and other aspects of life too!

Hope all is well with you and yours,



How interesting and something I doubt you would have written a few years ago.
Effectively you’ve come to the same conclusion as every seasoned flaneur – there is only one style, and that’s your own and it should be permanent.
Of course, you can throw a new element into the cocktail but that new ingredient should be consistent with the core recipe.
As for ‘fashion’, yes I do observe and comment. Usually in a derogatory manner!


Armani white tshirts? Isn’t his signature look a navy tight fitting one? Cheers


Another extremely insightful article. I agree about the tendency towards honing one’s own style while not loosing sight or interest across the landscape of men’s clothing. This enables your ‘ personal look’ to be achieved without multiple distracting choices every day without looking (and becoming) ‘staid’.
This really resonates with me especially as I approached and then retired.
I find your articles in a class of their own, always written in a conversational style and never patronising. Always something to look forward to reading three times a week.
Also very timely in that I have just stepped back from a potential mistaken purchase!

Valentine Hayes

Another wonderfully thoughtful article that applies to women as much as men.


A rather deep post that denotes a fair amount of pondering and growing maturity in terms of clothing, dressing and, in fine, one’s evolution.
A few years ago I noticed that my own style was starting to develop and being fine tuned; whilst going through some photos in Instagram I remember thinking to myself: “great outfit, lovely colours but I don’t see myself wearing it as it does not fit into my style…that is when I realised that my own style was subjacently present and developing.


Hi Simon,

Kamoshita-san is actually working under United Arrow.



Miles Fisher

Thoughtfully written Simon, as ever. You’re right about “most normal men.” As your buddy Bruce Boyer wrote many years ago; “The thing with obsessives is they seem to know everything about clothing except how to enjoy it.” Ah yes, the hardest piece of the puzzle…how to “enjoy’ in a perfectly “normal” fashion…


As to your baseball cap….Go Bears!

R Abbott

Individual styles evolve for a variety of reasons. Some of them are circumstantial: a young man at university will inevitably dress differently from a man in his late 20s, who in turn will dress differently from a man in his 30s who is married with children. Other obvious “circumstantial” considerations include which employer you work for, which city you live in, what social circles you spend time in. As these change, so does one’s personal style.

However, I agree that as people into fashion get older, they tend to refine their style – as they develop a better idea of what suits them personally and of how to dress appropriately for whatever occasion they encounter.

The biggest challenge for a young person who is interested in men’s fashion is how to avoid looking like he’s “trying too hard.” Some people never learn, but generally speaking, avoiding this pitfall requires a certain level of judgment and sophistication that comes with age.


Thanks, Simon, one of my favourite of your articles thus far. I’ve really felt this pull over the last five years (I am mid-forties) – often honing down to single brands and styles of certain items like t-shirts, jeans, sweaters, shirts – actually pretty much everything – and a much reduced palette. It makes life a lot easier, as everything fits and everything goes with everything, but still allows a little playing around with certain items and there are infinite more subtle variations of, for example, blue and grey.


Noboru Kakuta looks great all the time! He never looks repetitive or boring to me in any way. He is all about tone, texture and proportion, not to mention his confidence and ease. I think a lot can be learned from him if you look closely.


Love that cardigan that Kakuta has on! May I ask who makes that?


Most of the ones I’ve seen, including Drake’s and Colhays have welt pockets. Kakuta’s pocketless version is actually, to my eye, a nice and subtle variation that maybe looks cleaner without the horizontal line of the welt. I can’t recall seeing any 4-ply shawl cardigans that are pocketless like this one. @Simon do you know of any? I’m wondering if it was a custom order or maybe was only sold in Japan.


Thanks for the tip, Simon. The Begg cardigan looks nice


‘Honing Your Style’ in terms of refining and refreshing is, in addition to pure good taste, undoubtedly the trait that separates the gold standard flaneur from the amateur fashionista.
With this in mind, have you thought of following this up with a series of observational articles analysing the evolution of some distinguished flaneurs . Particularly those with a unique style ?


One interesting idea might be a series of capsule wardrobes by those with a unique style, in terms of what they actually wear themselves (rather than what generically might be worn most widely by a large net of people).

I remember an article where Michael Hill summarised his capsule wardrobe and included purple socks – which you could see really fits into what he wears, but I’ve never seen them in a standard capsule list. Others examples might be Jake Grantham’s babour jackets, or even Edward Sexton’s role necks.


Hi Simon….an interesting article which evoked some memories. Personally, looking back, I’ve seen a mixing of the styles that I wore when I was much younger (mid teens) but in a more refined and subtle way. This wasn’t a conscious decision, just a natural evolution of something I felt comfortable in, even at that young age. For example in the 80’s I would have worn a LaCoste polo shirt, Lois cords and a crew or v neck Lyle&Scott or Pringle sweater, with Nike or Adidas trainers (the terrace casual look, although I wasn’t a big football fan more interested in the fashion side) Now, in my late 40’s, after flirtation with various styles and fashions in the interim, that original look has been refined to I guess a relative ‘uniform’ of button down mtm shirt, a pair of Blackhorse lane jeans or tailored/mtm chinos/flannels, a crewneck sweater from a good mill or Sunspel sweatshirt, CP sneakers or quality benchmade suede oxfords and the obligatory Private White outwear. These are all generally muted colours, with the focus on quality and fit.

Dan James

Hello Colin,
Your comments struck a chord with me in my early 50s. The football casual look was one of the looks that started my interest in clothes. And now I tend to choose from navy, white, black and grey (dabbling in shades of brown for the summer) and stay with Sunspel, Kamakura shirts, trousers and chinos bought unfinished and then altered to fit. Found my style but not bound by it.


Gauthier Borsarello said something in his Handcut Radio episode that stuck: that stylish men were those who had spent time searching for style, and then stopped. His point was that the elegance arrived when the search was terminated. (If I remember correctly, this was followed by “But Aleks, you and me are fucked, we’ll never stop searching.” The eternal Catch-22!)


Well said Sam – I think I am fucked as well. A consumerism disease.

Simon – Don’t you think the style evolution you mention is based on trends? You mentioned tie bars and waistcoats which are pretty much out of trend and corduroy, baseball caps, t-shirt/shirt combination which are all the current trends.


Very elegant vocabulary.


My choices have narrowed considerably in the last 10 years or so. Several of favourite brands have been ruined or changed (for the worse IMHO) under new owners or management. Chester Barrie, Gieves & Hawkes, New & Lingwood, Thomas Pink, Hilditch & Key, Bates hatters, Hackett, Hawes & Curtis and TM Lewin (a recent disaster) are just a few examples. In the 80s and 90s, I would visit them regularly but not now. It is very sad to see Savile Row and Jermyn. Street icons being destroyed by hedge fund spivs and greedy conglomerates in pursuit of the fast buck.


I would say that there are two stages that happen during the process of refining one’s style. Maybe they are the early ones, maybe late – I truly can’t tell, I’m not there yet. The first is understanding that capsule wardrobes, lists of basics and so on are good until certain point. Some of the items there are useful to you, some are not. And wardrobe size is not really an issue. The assumption in capsule wardrobe lists is that everybody has too much clothes and only wears 1/10 of them because there is only so much days each year. It’s only partially true. The other reason is, most people have a lot of clothes they don’t like wearing – so they don’t. You could have 20 pieces in your wardrobe, or 33, or 10, and still not wear half of them. Hell, if all my wardrobe was made of Hawaii print shirts and joggers, I would just walk around naked. My point is, no need to bother about wardrobe size, up to a cerain point at least. Don’t buy what the internet list says – buy what you like and need. It even applies to posts like Simon’s capsule wardrobes, even though these are very good lists. I know that I won’t need any worsted suits, plain shirts, printed silk ties or even black oxfords. Or even from the most recent one, I’d rather have two brown jackets than brown and navy. Or maybe brown and olive. Or brown and charcoal. It’s just what I like – navy doesn’t seem to be my color. It’s not that Simon’s advice is bad – it’s great. But it just doesn’t apply to me in this case.
The second stage for me would be figuring out the clothes you really like, but are not going to wear. It overlaps a bit with the first point – I like 30’s style outfits, like the ones Ethan Wong used to wear. But there’s no way I’m going to wear them – they are very unusual and formal, much more than I would like my clothes to be. The other category are clothes that are too flashy for me, such as pop-of-colour cardigans, bright sweaters or rugby shirts. Those aren’t the clothes I hate – quite the opposite, I like them a lot. Whenever I see them in, say, Drake’s lookbook, my first thought is “I need one of those. Right now.” A few hours later, I haggle it down to having just one, for the times I feel like wearing something bold. Another few hours later, I realize that I never feel like this. The proces repeats every few months. So this is for all the clothes that we love to look at, but never actually wear. Maybe they are too bold. Maybe they are too formal. Or maybe they are the red/navy stribe rugby shirt, and you live in a neighbourhood where any fans of a football club which happens to have same colors were mugged at best and butchered with shivs and pitchforks at worst. Either way, you like them, but won’t wear them. Identyfing them will save you a lot of money and wardrobe space.


It appears that there is another, third stage. That stage seems to be realizing that if you keep circling around some things that aren’t practical to you, it’s maybe because you are attracted to them this much. And in this case, perhaps it is worth to give them a shot and see what is stronger – your fear or wearing them or their appeal. Maybe you need versions of them that are toned down – for me this is crimson sweater rathen than bright red, or knitted blue and navy stripe rugby rathen that the brighter colours RL Polo tends to use. Maybe it will work, maybe it won’t. It did for me, even though I am still looking for that perfect cardigan. In short, don’t cross out things you like because they are too intimidating to you.


Really enjoyed this write-up Simon.

Your conversation had me wonder – it is easily for us within the classic menswear realm so to speak, or people in fashion to hone their style, since we spend so much time thinking and experimenting with it.

The question, then, is how do you convince, or at least influence, people outside this circle to do the same? Most of the time they don’t even care the importance of having a personal style.


What makes you think more men are interested than were twenty years ago ?
I doubt that – visually I see no change .
The menswear market has grown significantly over that period, as have many other markets, simply because the one percent have got significantly richer and dump more money on ‘stuff’.
That doesn’t denote a change in those interested in style because you can’t buy it !
I think it’s important to understand this because businesses like yours will only survive and thrive if they market to the core flaneurs who are truly interested in aesthetics and quality.
You do a pretty good job at that but dilution and fads are the enemy and I for one want your success to continue.


At the end of the day, it’s really not that important. Sure, people write about it and try to make a living out of it (see food blogs, wine blogs etc) and that’s all fair enough but sometimes it’s also rather mind-boggling how people totally forget that they’re part of the 1% lucky enough to even care about those things. People writing in around here and asking Simon whether they should do this or that – people, seriously, if you’re that easily flummoxed, stick to the basics (as the late great Monsieur Tang once said, if you have to ask, you’re probably too insecure and unfit to wear it).
Enjoy it but don’t take yourself too seriously. Dress for the occasion and brace yourself for the ridicule if you do not.

Kev F

Anonymous, I very much disagree with your view of “if you have to ask, then don’t” stance. Does that apply to everything so if you are unsure, for example of which laptop etc to invest in you shouldn’t ask advice? One of the values and pleasures of this site is being able to read views and ask for advice if necessary. I assume with bespoke and MTM then you have to communicate with the tailor, cutter etc but it’s great to also get that service and advice in places often mentioned here – Trunk, Drakes, Anglo and the like. Apart from their clothes often being better you can’t get that service in the vast majority of shops.


Oh baseball caps, have we reached peak #menswear yet again?


I think a lot of it just comes down to what is wearable in our everyday lives. Workwear, overly structured suits, avant garde clothing, pocket squares (other than very subtle ones), vintage clothing, etc. just won’t be very wearable for most people in many situations: the workplace, dinner parties, medical appointments, going to the grocery store, or taking the dog for a walk.

I think there is a tendency for many men to want to dabble in each genre, rather than to confine oneself to one genre in particular. I think it is one of the strengths of this site Simon that you show off so many different things (this site wouldn’t be very good if you just showed the same 5 or so outfits over and over again); however, I think the range of dressing you show on this site probably doesn’t make sense for most people from a style-perspective. I also think that over time, this urge to dabble in all sorts of things goes away.

As for my personal style, I think a lot of it comes down to my aesthetic tastes, wearibility and versatility: OCBDs, shetland sweaters, suede Alden shoes (more versatile than many sleeker options), tweed jackets, and other Ivy-ish items. I can wear the OCBDs in 95+% of situation–even with a suit (which might be too American for many). Shetland sweaters look great in so many situations. In sober colors, they are wearable in many offices, but they don’t look too corporate at all so you can also wear them outside the office, even on a walk through the woods, or at a festive meal, perhaps under a jacket. They also come in many wonderful colors. I could go on.

I tend to experiment most with color and cloth, rather than with cut or style.

Stewart Bone

Great photo with the coat and cap. You really nailed it. The cap needs to be just right. It is so.


Anonymous referenced a quote stating that, ” if you have to ask, you’re probably too insecure and unfit to wear it”. Well, I think this is exactly the type of stance that has put off so many men that may be interested in classic clothing or, more broadly, clothing in general. If people felt confident in asking for help then the climate would be totally different when it comes to purchasing clothing. My favorite retailer in the US is Sid Mashburn. His entire business is built on making people comfortable and secure during the shopping experience. The staff is open, accepting and very willing to help in any way possible. And I feel that this type of experience is helpful in honing one’s personal style because it allows for open discussion and communication. I think, in some ways, this is very similar to this site and the comments section.


Dear Simon,

Thank you for coming up with such an interesting topic.

May I add that it does not only apply to mature men. Here is my 27 years old menswear geek perspective:

For the past two years, I went through all I could read, watch and learn from you and others about British and Italian tailoring, workwear, vintage military, Ivy stuff and so on. I started to buy many things and tried out various styles, sharpening my eyes and taste through Instagram at the same time. I made mistakes like everyone else but it made me realize what really suits me, and what doesn’t.

Thanks to lockdown, facing my wardrobe for two months made me go over it to find out what were the core elements, things I would genuinely enjoy wearing everyday according to my work environment, daily life and personal preferences. From there, I sorted out my bolder pieces, keeping what was the most coherent with the overall and got rid of more superfluous items I thought looked great on influencers but not on myself.

It was painful to let a whole range of different style options behind but It’s also relieving and exhilarating to have nailed what truly resonates with my own taste and personality. I have a clearer vision of what I want to dig and invest in and realized that I needed to reduce my palette and make room for more specific items, colors or textures to truly develop my own style.

In other words:

Less is more
To choose is to renounce

Cheers !


Men should feel completely comfortable asking questions on PS about any matter of clothing, style, appropriate dress for venue etc. After all, isn’t that why we’re readers? Personally, I’ve learned a tremendous amount from Simon, and other readers, that has been very helpful in my sartorial choices. So, gentlemen please don’t be shy and ask away. Your questions, and the answers, help all of us in some form.

Matthew V

Another great article.

My own style has definitely been honed over time.

Similar to Colin further above, having been through the Casual phase, but with a constant interest in elements 60s / Modernist style, and happily settling on button downs, good quality chinos, selvage jeans, John Smedley and similar knitwear, Common Projects, C&J shoes, Neapolitan influenced tailoring (mainly Anglo Italian) and Drakes ties, with T shirts and sweatshirts from Sunspel and the odd curve ball thrown in (sometimes purchased out of curiosity but ultimately not worn much).

I have to say I enjoyed the freedom and new ideas for men’s fashion during my more experimental days in late 1980s / early 90s clubland.

As I am post 50 (in body if not in mind!) my wardrobe is now mainly shades of navy and denim blue, with an increasing about of olive green creeping in.

One thing is for certain. I will always be interested in clothes. I just don’t understand people who have no interest in what they wear, but each to their own.


Hello Simon,
I really appreciate reading you articles every week. Perhaps I’m being overly pedantic, but I think the word hirsute, at least how we use it in medicine as in hirsutism, refers more to excess hair growth on face and body, and little to the scalp. Men therefore tend to grow more hirsute the older they get, despite male alopecia, because of testosterone induced increase in facial and body hair. Oppositely a male teenager with a full head of hair, but no hair on the chest or arms, would never be called hirsute. Keep in mind that I’m not a mother tongue user of the English language and there is an obvious risk that I’m not aware of the current usage of the word.
Regards Morten

Initials CG

Probably long term adverse affects from reading too much Tolkien in one’s youth…. combating hobbit ears as you pass forty becomes another part of the morning routine


I think most of us geeks go through the same rough stages.
1. You get into clothes, read up on and adhear to all the rules, get all the basics.

2. You consider yourself a lot more knowledgeable than the average joe, and start wearing a lot of bright and fun combinations, mixing colors and patterns like never before. Why? Because you know the rules so you can break them, damnit. (A mental picture of myself in my mid-twenties comes to mind; purple checked shirt, yellow v-neck, rust red cords and chestnut shoes, and a big purple scarf on top of it all, since it was winter.)

3. You get over the crazy phase and hone in on the stuff you come back to, most likely a variety of blues, greys and neutrals/browns.

Tommaso Capozzoli recently posted a slide show which I re-visited after reading this post. One of the shots is from 1992. He’s in a denim button down and tweed jacket, looking just as good as he ever did. Looking that timeless is what I will always aspire to.

PS. As it happens, shortly after seeing that post I was sent a picture of myself from 12 years ago. Pushing a friends baby on the swing, wearing khaki just above the knee shorts and an old blue OCBD, just as I was when opening the email containing the picture. I guess that counts for something, ha.


But but but those are from the color wheel article! So that’s not how stylish people dress?! /turns off sarcasm font
I’d also say who “told me” to dress like that but I guess Simon won’t appreciate taking shots at other menswear bloggers :c


Lovely piece, Simon, and it speaks to so many things I’d been thinking about my own style but hadn’t been able to articulate. In an episode of the Unbuttoned podcast series with G. Bruce Boyer, Pedro Mendes says his love for tailoring and elegant/smart clothes really took off after he had his first child. Though of course there are many, many more important things you hope to impart, having recently become a father myself, at 39 I feel like I understand what he means and that it’s played a huge part. There’s something in there about the man/person you want to be, both for yourself and for those you love the most. Clothes are a small part but they’re still a part, if they’re something you care about.

I’d also say that one of the benefits of honing your style is finding a new lease of life for items you bought years ago that suddenly work better and with renewed purpose in your wardrobe; it can almost feel like you subconsciously bought them with an eye to your future self. But it’s a double-edged sword. I had three pairs of Japanese 501s, bought fifteen or so years ago. One I always found slightly high-waisted; the other two were worn all the time, much-loved, but developed holes that – idiotically, naively – I didn’t have the imagination at the time to conceive of fixing. A few years ago, during a clear-out, I gave them all to a charity shop. Of course now I see the high-waist was a boon and could easily get the holes in the others fixed. I still think about them, with unhealthy amounts of regret. Hopefully they found a good home.


The great thing about this forum is that it is peopled with intelligent (and for the most part polite) readers and hosted by an insightful, erudite blogger. You can therefore generally depend on the views being pertinent and that the recommendations are ones worth following. That in turn has led me (and I’m undoubtedly not the only one) to look more carefully before I spend money on an item and to perhaps buy more expensively, but with more thought and with longevity of the item even saving me money in the long run. I, like many guys who hang on to ‘stuff’ when they shouldn’t, still need to comb carefully through my wardrobe and ditch what I no longer feel good wearing.

To be comprehensive, this piece, Simon, should consider what happens to the divorcee. There are so many if us these days. The new partner comes in and immediately has a rummage through the man’s wardrobe, The new partner tells the guy what the partner likes and doesn’t like and what would will look good on him. His carefully honed opinion is immediately warped! And if the new partner has not got good taste, that opinion can have a deleterious effect. Nothing looks worse than the middle-aged guy one so often sees around town who looks a complete berk in clothes that really do not suit him, and which would sit better on a man 20 or 30 years younger. I’ve been pleased that your articles on the more casual look that you have adopted since working at home, and which will be forced on so many more of us post-Covid, have remained true to what looks good, rather than the inappropriate down-dressing or down-ageing that one sees.


If it takes decades, I’m ahead of the game I suppose. In my early 20s I woke up to style and went through the requisite “dressy = good” thing. Since then I’ve bounced around the spectrum before settling into a considered style combining cues of workwear, skate/rocker and “smart casual”.

Peter Zottolo

Enjoyable to hear varying viewpoints of those in the industry as well as everyone’s comments. I like keeping tabs on what trends are, not to slavishly follow them, but rather because clothing can be re-contextualized in ways I’ve never seen before. Granted, it’s not always to my taste, but sometimes it is, and gives me a new, modern way to wear something I may already have in my closet. That way experimenting can feel familiar instead of stepping too far outside of one’s comfort zone.


A little late to the party, but a really interesting read. I think we hone our style subconsciously as we grow older. As I approach the big 4-O my wife and I have an in-joke whenever a package arrives in the mail. “Another blue shirt?” she always asks, and half of the time she is right 🙂

One thing you didn’t really mention in the article is how seasons might affect your ‘dress code’. I have generally narrowed myself down a palette of blues, greys and olive greens, but in summer I don’t mind adding a pair of brightly coloured shorts or chinos. Having said that, I wouldn’t wear anything too colourful on my upper half as I’m aware of the colours that work for my skin and hair tones.


Thanks, Simon. Another great idea for an article, followed by great execution.

I have always found the idea of being able to learn how other people’s style has evolved to be interesting and potentially helpful. Not to date myself too much, but I remember that in the late 70’s GQ had a regular column called “Why I Wear What I Wear” that was informative and interesting. I think there is a rich potential for you to explore with that theme.

The mention of Armani made me think his quote when he was explaining that he dresses himself very simply: “I don’t have what you might call a designer’s wardrobe.”


Hi Simon, thanks so much for your site!
I would like to ask you a simple question: any advised to begin to wear like Naburo Kakuta? I did not know him until I read this article, and I was surprised he wears the same colours I usually do. I am quite younger than him -I’m a 33 years old spanish guy- but it seems to me he wears stylish and simple.
Many thanks for everything and specially for your site, I am really enjoying it a lot!


Thank you very much Simon!
You’re absolutely right, so much blue is too extreme for everyday. Normally in winter I wear grey trousers to work (I’m a tax lawyer, although now with the pandemic there are almost no client meetings, so the outfit is more relaxed) and beige chinos (sometimes navy blue) for the weekend, and navy blue blazers, jackets and sweaters (depending on the moment) with light blue or striped shirts. As you can see, I’m not very original hahaha.
Thanks again!

Carbon Esque

Very thoughtful post, Simon. Your points on the honing of style as one ages are, I suspect, true not just for clothing but also a myriad of other interests. I also have a website. Its niche realted to winter clothes. If anybody want to purchase online then contact us.


Very pensive post, i think it all boils down to how much dressing sense you have , like the more you dress the better you’ll become at customizing and honing your style