These are the tools: you have to use them

Monday, April 5th 2021
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“Can I wear dark-brown shoes like these with a suit in my office? Do you think it would be appropriate?”

The answer is, I don’t know. I don’t work in your office: I don’t know what the implicit dress code is. You have to make up your own mind.

I can explain why things are more formal or less formal. I can show how things of a similar formality - or style, or tradition - go together. But you have to judge the context. You have to decide what’s appropriate. 

Essentially, websites and books can give you the tools, but you have to use them. 

Actually, more than that: only by using them yourself can you develop your own sense of style.

In recent weeks a few Indian readers (going by their names) have been asking about some of the fundamentals of dressing smartly: what shoes go with what trousers, how to dress smarter without wearing a suit. 

They are clearly learning from scratch and are admirably curious and self-aware. But there comes a point where I can’t answer their questions. When they have to take the tools they’ve been given and apply them to their culture and context. 

I think this theme - of learning from others and then from your own experience - is an interesting one, because it doesn’t just apply to guys starting from scratch. 

Even when you’ve been dressing well for a while, and consistently look both appropriate and flattered by what you wear, you might not quite have developed your own style. 

This personal style is often what makes people great dressers. But it requires both a knowledge of the basics - which may have been consciously learned or subconsciously absorbed - and then consistent play and experimentation.

Returning, first, to those readers just starting out. 

One wanted to know about trousers: why suit trousers are often too smart, sharp and smooth to wear with casual jackets. 

They might learn the answer by reading about tailoring cloths, and the difference between worsteds and woollens. Or, they might learn the principles that smooth, sharp, dark, plain materials are smarter than coarse, loose, bright, patterned ones. 

Either way, once learned these things should become intuitive. So that when they look in the mirror at an outfit, they know the trousers look wrong with the jacket, and that they need to be swapped for something more casual. Those principles they initially read about have become instinctive, involuntary. 

It’s easy to scoff at people that learn this way. Those that do scoff, however, are obeying the same principles. The only difference is how they learned them.

It might have been from their parents, who simply showed what looked good every day. Or it might have been from talking to their peers: girls do this intensively, I find, and a lot more than boys.

If you had none of this early education, you need to learn it more explicitly. And reading it in an article is a lot quicker than years of osmosis. 

When you do learn like this, it can take a little encouragement to apply the ideas yourself. 

Another of those readers, for example, asked about the social situation in bars he went to. Everyone else wore shirts and trousers or jeans. No one wore a jacket or tie. Would he stand out if he did? 

I assume so, yes. Certainly I can’t tell him from all the way over here.

But if he’d like to dress better without standing too much, I can give him some tools. For example, understanding the sliding scale from structured blazer, to soft-shouldered jacket, to completely unstructured, to overshirt. 

Each is more casual than the last, and he can pick where he wants to be on that scale. 

Another tool would be understanding which colours look smarter than others. Or why an overshirt with epaulettes, bellows pockets and a pleated back draws more attention than one without. 

Now let’s jump forward in time, to the more experienced dresser.

Last week I got talking to a reader who lives locally. He’s been a fan of the blog for years, bought clothes in most areas we’ve talked about, and built up a nice, quality wardrobe. 

He was wearing an old, belted Belstaff jacket in a size bigger than I would have worn. He was wearing a denim shirt and jeans in pretty much the same shade. He was wearing trainers in fluorescent colors. 

But he looked great. And as we chatted about the pieces, what he liked about them, it occurred to both of us how he had built on those early principles over the years. 

He understood good fit, and knew the advantages and disadvantages of the oversized jacket. It had an slouchiness to it that he liked, but he controlled it by keeping the belt cinched. 

He knew very well that double denim was more risky, more of a ‘look’. But he had chosen that to be more unusual, to be more playful. He did it quite often.

The trainers were certainly bright, but they were fairly slim too - Nike Daybreaks, I believe, in yellow and turquoise. Their silhouette fit in very well with everything else, even if the colours stood out. 

And he’d done it all instinctively - not spelled out as it is here, but quite simply and naturally, because he simply understands clothes.

I only wish he’d allowed me to take a photograph of him. 

Clothing can be helpfully thought of as a language. Some people absorb it when they’re young; others have to learn it when they’re older. 

Whatever the method, the more you learn, the more you can express yourself. And that’s the journey most people are on with clothing. I certainly am. 

I very much look forward to those new readers growing in confidence with their clothing, and starting to wield these tools (to switch metaphors) themselves. 

I hope they continue to read, comment, and help others that are just starting out too. 

Clothes pictured:

For more on the 'rules' and how to understand them before breaking them, see the Guide here.

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Bit of a tangent but I’ve been reading about the Toyota production system / lean manufacturing lately and there’s something of a similar dynamic. One of the writers says that he is often asked a common set of narrow questions that boil down to “how exactly do I apply this system to my particular industry?” or “how can this particular tool be used in my work process?”. The real answer to these questions is that the whole point of the system is to think deeply about the work being done and through that, solve problems and find improvements. Specific items like kanban cards (or worsted trousers or dark brown shoes) might be helpful but it is really about understanding how they work and making them apply to your situation, not just blindly implementing them.


After being a long time reader I’ve recently started on a process of rebuilding my wardrobe, based at least partly on the capsule series of posts.

I created a kanban board as part of the process and have found it really helpful for considering different ideas and tracking what I’ve got to work with.

Peter Hall

One of the most important lessons I discovered was to take the time to enjoy what I was wearing. VIt’s so easy to just check list your acquisitions… As my wife mentioned, it’s not an arms race… Take your time.
I find look books very important. The more exposure to difference the better.

Dr Peter

Great article, as usual, Simon. I think the points you make are all well taken.

It doesn’t matter how you learn the general rules, you must understand them and then learn how to break some of them. In the end, achieving a style that you can call your own is the ultimate goal, no matter how you get there.

The one thing I would add is that style, which is a reflection of your personality, is much more than clothing. The critical thing is to allow your clothes to reflect and enhance your personality.


I couldn’t agree more with your last paragraph.
I like PS because it brings quality brands and services that I probably wouldn’t have noticed to my attention.
Notably the likes of ‘ Begg & Co ‘, ‘Equus Leather’, ‘ I love Cashmere ‘ and the like.
Not to mention some great PS collaborations.
I also like Simon’s forensic analysis.
That said, when it comes to ‘How To Dress’ , only the individual can decide that.

A lot of men tend to think in terms of fixed rules – like an engineer. Maybe a lot of the people who can afford clothes like the ones discussed on Permanent Style are with a background in fields like engineering, finance, law and this is how their brains are wired to think.
They want an algorithm, a recipe on what to do dress with style.
The idea, that the rules are not realy fixed and not valid for any environment is not something that people like.
Honestly – from my bespoke journey I profit the most from bespoke shoes. Because at the moment I would not always wear a jacket or even a shirt, but I always enjoy wearing nice bespoke shoes and they fit almost any setting – even very casual one.


Always enjoy your comments Hristo, but if your lawyer thinks like an engineer then you need to upgrade her or him!


When I was a newcomer to menswear ”the rules” were very important to me. I know realise that the important things with rules is to understand them. It is very easy to remember rules (no brown in town, not white after Labor day and other more or less stupid rules). It is much more important to understand them and why for example a tweed sportcoat is less formal than a navy blazer, and why they are suited for different settings. It is much easier to break rules that you understand. That is the reason why articles that you find on Permanent Style is much better than the ”Manuals” you find in GQ or Esquire.


Simon, your guidance has been invaluable in laying out the clothing that ranges from informal to formal. Rather than formality, I was wondering whether you could tell me what you think of as the most academic suit. I am a professor in the US, and while I wear brown tweed and grey flannel on non-teaching days, I prefer to wear a two-piece and tie when I teach. I currently wear soft worsted navy suits, but they still feel too “business” to me. At the same time, what I want is not something just more casual than a navy worsted, but rather something more academic which I think is a different criterion. Could you tell me your thoughts on this topic? Are dark brown gabardine and brown cotton-linen glen check good fabrics? Assuming shoulders should be soft/natural, should I be looking for an extended or narrow shoulder? How does a double-breasted compare to a single? What do you think of as a the paradigm of an academic suit? Your help would be much appreciated!


Thank you for your replies, Simon and others. I should clarify that I already know the most popular suit among my colleagues when teaching is the navy/grey worsted. Thus, my question is not about what my colleagues wear. Insofar as clothing is a language, I am wondering what kind of two-piece communicates that the wearer is an academic rather than a businessman (which is what the navy/grey worsteds communicate, at least in my mind).

I am surprised to read that you seem to think that those around me would not notice the details that greatly affect the look of a suit such as the jacket’s shoulder. That seems to go against much of what you’ve written about on the blog. Could you explain what you mean when you say others will not notice the difference between an extended shoulder and a narrow shoulder?


Maybe you’ve come to the point where you must decide who YOU want to be, regardless of any thoughts of appropriateness or preconceptions. What is YOUR style? What feels most comfortable to wear? Try different outfits and see where they take you. As a part-time teacher myself I take every opportunity to enter the ”stage” in a new outfit/combo. If you stay within the realm of classic menswear you can never be truly wrong.


As a professor myself I am happy to explain that the quintessential US academic suit and consists of baggy khakis, ca. 2008 New Balance Sneakers, and a slightly too large mid blue shirt with a white t-shirt underneath. For conferences, round this off with a mismatched charcoal suit jacket. Glad I could be of service here!

Serious answer: Nobody cares as long as you’re smart and don’t smell.


When it comes to reading your articles, I find the comment section just as helpful a tool as the article itself. For that reason, may I suggest adding sorting features to the comment section? It would be helpful to readers if we could sort comments in different orders (latest comment first /oldest comment first) especially when revisiting popular or older articles such as “The Bespoke Tailors I have known” which has 270 comments , some of which going as far back as 2014. Sorting comments in different levels of engagement so the comments that have generated more responses appear higher in the section might also be helpful. Some comments may become outdated over time; some are not as relevant to the discussion. Being able to sort comments in several ways would keep discussions engaging regardless of how long ago an article was published.


Really nice article .
“ If you had none of this early education, you need to learn it more explicitly”…. … someone who was a little sheltered and learnt later in life about a lot of social things I can confess that late learning can be embarrassingly painful.
Men can be lacking in empathy.

I’d certainly like to see other articles like this with real examples of how individuals get things wrong and how they can be improved .
Very often it’s only little changes that are required.

Men particularly have no understanding of colour and so often revert to a safe grey or navy.

R Abbott

Ultimately, dressing well isn’t just about looking sharp – it’s about projecting an image, perhaps even a set of values. Although we live in a culture that purportedly prizes “non-judgmental-ism,” the reality is that all human beings instinctively make certain initial assessments about other people based on what they wear, and the less you know someone personally, the more important those instinctive assessments become.

Simon: you mentioned that women are often more aware about fashion trends because they talk about it more as girls. There’s an obvious reason for that – for whatever reason, people tend to judge women by the clothes they choose to wear to a greater extent than they judge men, and so, it’s not surprising they talk about it more when they’re growing up.


Great article, Simon. I’ve spoken to lots of friends and peers who swear that their workplace (backs and law firms) insist on particular colours for suits, ties, shirts and shoes.

When you dig deeper those strict rules aren’t written anywhere but more about how your peers react to what you’re wearing – usually, what will potentially give rise to teasing and other negative behaviour.

I’ve rarely ever come across a workplace where you can’t find people dressed in all manner of shades of suit, shirts, ties and shoes. Ultimately it comes down to how you feel and whether you want to fit in or stand out or be somewhere in between.

Humans are social animals. The exact same considerations apply to how you dress when you’re at a bar.

For me? One of the best things about younger generations is people are less likely to judge others simply because they look or dress or act differently to the “norm”.


Loved the encouraging post.

Personally, I think the problem when starting out is the lack of perspective, vocabulary and landmarks to allow you to identify elements. A lot of the time it can be grasping at straws. (The menswear world can be especially challenging which can inhibit accessibility for those just dipping their toes.)

Without developing the necessary tools, (via hard graft or some guidance) why you might like a particular aesthetic or outfit remains illusive and prevents you from drawing a roadmap to get to your desired destination. The inability to understand why/how your favourites have put items together to produce the aesthetic you like makes it a lot harder to then move on to develop your own point of view.

I think resources such as Ethan Wong’s recent discussions, Mark Cho’s ‘what am I wearing and why’ and your more personal posts are very helpful to empower others to develop the tools to create their own point of view without being overly prescriptive.


I found this blog by accident a year and a half ago and have now built a fairly good starters’ wardrobe, but more importantly, with the help of information provided on this blog, I have found my own style and taste with classic menswear. And an important lesson is that others’ style, and even “rules”, are no more than sources of inspiration, you have to make it your own to look natural and make yourself comfortable.
I was quite against the idea of tailored suits and jackets for non-formal occasions before I moved to London five years ago, mainly because many of these classic menswear enthusiasts in Asia are trying too hard. In Shanghai, in the eyes of locals, especially elder generations, these people were always mimicking lower-ranked gang members of the 1920s and look really stupid in their nicely made suits (just imagine going to the row and order an outfit based on Peaky Blinders, not as a costume but daily wear).
But in recent years I’ve realized that I’m almost at a stage in life where I need clothes that can be worn for at least the next decade, and classic is the only way to go. To me, two elements of Permanent Style made it became almost the only source for learning and inspiration when building my starter’s wardrobe: 1. its focus on quality; 2. Simon really looks comfortable in (most of) his clothes. Simon and this blog have provided us his knowledge, his experiences, and his perspective, we readers shouldn’t expect these, or anyone other than ourselves can change or improve our taste. My taste and my preference for most things certainly haven’t changed with changes in my wardrobe. I’m still don’t and don’t want to own any jeans, to me they can be substituted with either tailored trousers or tracksuit bottom depending on the outfit; I still won’t dress like these “enthusiasts” in Asia I mentioned earlier and I still think they look silly; I still won’t own an SUV unless I move to North America; and I still don’t like Roman numerals on dials.
Thank you, Simon, not for being an “authority”, but for sharing.

Patrick Bateman

Another great piece. Do you change your approach to what you wear depending not only on the social circumstances but also the people you will be meeting? For example, my local when it reopens, is a real melting pot of people who have made an effort for a Friday night out, people who have stepped in from the building site and people who don’t seem to care. It makes deciding what to wear quite challenging!


A pub is, at its heart, meant to be an egalitarian setting – as you’ve pointed out, there’s often a pretty diverse mix of people, and broadly speaking those people (unless they know you personally) wouldn’t give you or your attire a moment’s thought unless you give them a reason to. Why not wear what makes you comfortable – it will put your mind at ease that you’re not standing out for the wrong reasons.


Hi Simon, another thought provoking article – thank you.
For my part and at my more mature years, I tend to think more in terms of ‘guidelines’ rather than ‘rules’. I agree with the comment that look-books are helpful. Similarly, the combinations you put together. They suggest ideas we may not have previously considered and can be adapted (not slavishly followed), into ones own style. The above I think thereby engenders the evolution of a personal style.

Matthew McIver

Thank you, Simon. I’ve been a fan of the blog for a while, and found your clear, structured thinking on formality and what goes together immensely useful, even though I get my clothes from vastly different sources than you do. But the underlying thought process has helped me as I’ve developed my own approach, and investigated the makes/looks that appeal to me and fit my budget. The deeper understanding of the codes and interplay of formality and occasion has helped me develop a sense of my own clothing as a wardrobe, fitted to cover various purposes, rather than a haphazard collection of stuff I once liked. And as I’ve explored contemporary off-the-rack makers whose style appeals (I own more pairs of Spier & Mackay pants than probably items from any other maker, except possibly for deeply discounted Jos. A. Bank vests) and pre-owned quality items, I have an intellectual framework to pull them together into something that hopefully resembles a coherent style. I attribute a lot of that understanding to you thoughtful work–thank you.


Jason, I’ve spent a fair bit of time around academics both side of the pond and I find suits the exception really – but depends on discipline.

The chino/sports coat combo seems more common. I use a mix soft shoulder jackets, like the cashmere one here (but not as nice obvs) and chinos, flannels and other mixed trousers, with a few non-silk ties. I find the sprezzatura fits academia more than the classic suit (business schools being the exception)
Something like this jacket is a solid foundation.


Hi Simon…I’m glad you wrote about this and your meeting with a local reader. Too many people think that one can just dress well by ‘following the rules’ or dressing like people they have seen on IG (in ridiculous overdressed outfits, worn at home or on a photoshoot) Most well dressed people (rather than those playing at it for effect) develop their own style, don’t think too hard about it and subsequently may get it ‘wrong’ sometimes! Good that you showed an image if the brightly coloured Nike Daybreaks, rather than the de-facto CP’s, that many seem to think are always needed!


All very true but I keep thinking that the most stylish people I know did not necessarily have any education in this field and wouldn’t consider for a minute reading a website like Permanent Style – capable of dressing themselves in natural and well-executed mixes of qualities, colours, materials and styles without studying individual pieces or ensembles to death. People like myself, the other readers/commentators of this website and Mr Simon C himself clearly lack some of the raw talent to pull this off and have to resort to researching, analysing, considering and discussing every single element – online or offline – to learn the rules and then play with them. Nothing wrong with that of course – and I L.O.V.E. the website – but I always think about this when I hear or read the phrase “Permanent Style”


“…girls do this intensively, I find, and a lot more than boys”. This is a broad sweeping generalization, but one that I subscribe to too. I have learned most about style fairly subliminally from my wife and her sister. Not that I’ve ever asked or they’ve ever offered guidance, but they are each extremely good at wearing what works well for them. All it took was observation, and taking note whenever either of them complemented what I’d worn.
In general, women are great at knowing what works best for them.


The occasions that traditionally requires a suit and tie (weddings, funerals etc) will likely and hopefully not change. But it sounds like in many places, the few offices that still had a more elaborate dress code than “no shorts or sandals, look neat and tidy” might have loosened up too.
This means a lot of guys won’t have to learn to dress for the office, but rather they can teach themselves with a bit of the pressure off. They can take their time to read and learn, to go through a bit of trial and error and make their own occasions.

Having been in jobs with almost zero dress code, or even official uniform, I wore a tie for my commute for my own enjoyment. Vice versa, having worked in corporate offices where suit and tie were mandatory, it effectively killed the pleasure of dressing for me.

If anything, I’m a firm believer that Covid will solidify our opportunity to wear what we what when we want purely for our own enjoyment.
Guys should take that as an opportunity to try more things out and enjoy the process.

It’s just clothes after all.


The one thing I’ve always known about myself (and Steve Jobs and Henry Ford knew this well)…

“Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!'” People don’t know what they want until you show it to them.”

I wanted a specific kind of white jacket at age 6 after seeing a Toto video (the entire band is wearing some variation of a jacket I could never find when I was a child, but I kept pushing my mother to find it for me) –

I wanted another kind of white jacket at age 23 after seeing a Notorious BIG video (minute 1:43) –

At 37, my sartorial world opened up when I found this Pitti Uomo video of Aaron Levine and his remarkable ready-to-wear collection from Hickey:

At 43, I came across this amazing windowpane cashmere blazer by d’Avenza (28 seconds in) –

Until I saw it – I didn’t know what I wanted…

Indo European

Not sure why you had to call out “Indian readers” specifically. Wouldn’t it have been enough to just refer to “readers” rather than “Indian readers?” Adding the qualifier “judging by their names” doesn’t help much either – it still leaves the implication that naivety in dressing is somehow a general characteristic of Indian readers, which I’m sure was not your intention.


I too noticed that passing statement.

How do you know they were Indian? Did you ask for their passports? By your own admission, you made a judgement “going by their names.” When you write that you’d be losing something if you were to omit “any such nice detail,” you’ve made an assumption that you could have verified but did not, thus these details just your own impressions, not facts.

Don’t judge a book by its cover. Don’t judge a person’s history and heritage by his/her name.


I thought you were taking a risk in identifying the race/nationality of people asking questions. But I’m sensitive, having been falsely accused of ‘making a racial comment’ by someone of a different race to mine. There is heightened sensitivity since the BLM protests earlier this year.However, the point about not knowing the context and norms for those enquirers is valid, but I’d be inclined to be more diffuse by writing ‘enquiries from people living/working in the tropics’ or similar.


Simon –
I thought that detail (about Indian readers) was included to make a point about the “distance” from where you sit in London, and that another culture (despite the horrors of Colonialism, of course) may have (or may not have) a different set of social conditions, cues, and manners of dress. I read that your point was: I’m not living in your neighborhood, nor drinking at your pub, so, “No, I can’t speak to how you’ll be received, sartorially.” We are living in a world that is quick to “call someone out” (and subsequently cancel their POV and even their very job), instead of “calling someone in”). To me, the distinction is one worth making. I can’t think of anyone who takes greater care to be inclusive (in the world of style, fashion, retail, and dress) than Simon. He’s also utterly egalitarian: there’s no requirement that you “understand anything” to be a part of his blog, or to enter his world. There’s no payment requirement for readership. There’s no condescension. I just knew that someone would be “pissed off” by reading Simon’s assumption (they’re Indian, perhaps, because of their names), but it’s no different than my wife thinking I’d be black when she first met me, because my name is Wesley. That Simon is seriously considering the circumstances and social conditions of other cultures is the very antithesis of racism or xenophobia. I’d rather “call Simon in,” as someone who makes everyone a part of the conversation, instead of working really hard to police language that is (allegedly) creating some kind of divide. What Simon did here is not the same as saying to a friend, “I was in line behind an Indian guy at the ATM,” — drawing some needless racial distinction between “that guy” and the other white guys in the line. What he did (in this post) was to say, “One’s specific set of circumstances dictates what he should feel comfortable wearing…” But even then, I got the message that, “Even if you’re a bit out of step with your surroundings, your style – is ultimately – your style.”


A very thoughtful and considered response to the discussion. That said, your point, as effectively argued as it is, is based on assumptions as to the context of Simon’s passing line; those who are questioning the use of the line and suggesting its implications may be offensive to them are also basing their arguments on certain assumptions that they have read in to the line. With all due respect to Simon, his thought process behind including the point and intentions for doing so are absent from the page, which will ultimately leave people to question and draw their own conclusions based on their experiences/biases. I suppose one of the benefits of having an online presence and comments section is that these ambiguities can be reasoned out and re-contextualised by the writer in a way that wouldn’t have been possible in print.


I think it’s understandable given the overriding message of the piece that you would want to include that point of specificity; I didn’t see it as a generalisation or propagating a stereotype. That said, I’m not Indian and am therefore not coming at that line from an experience of cultural stereotyping that might give rise to that assumption.


Not to resurrect this discussion, but I too read that a little uncomfortably at first, and then went over it again with a grain of salt to make sure I wasn’t reading anything into it. Not being part of the named group may change things a little. I definitely see the point you were making with it about cultural differences, a very important one at that, but I think as with everything these days it’s worth being mindful of how our language leaves room for discomfort and uncertainty about those things. I see how someone of a certain identity could read a sentence where their identity is explicitly named and feel a little taken aback at first, regardless of good intent behind it. I hope said readers can express those feelings and still take away the good advice within, and maybe for the rest of us who write anything about anything, it’s just something worth keeping in mind for the future.

Cashmere Boy

Sorry to add on to an uncomfortable subject, but I would agree with the above poster’s comments, however I have to admit I did assume it was your intention to bring that presumption about a specific group of readers.

Also, lots of people with Indian names living in places like the UK, so it seemed bizarre to make the leap you did.

I’m happy to see that you clarified your intention, but in my opinion, your defensive response undermines it a little. My suggestion is that feel free to “lose something” going forward and leave out these “nice details”.

Be well.


I am progressive that normally reacts quite strongly to ethnic stereotypes. But I can’t see anything wrong in Simons writing here. He just gave an example of the difficulties of giving detailed advice on how to dress in another cultural or professional setting. I think it is very important to react to racism and prejudices. But that becomes harder to do when nothing is intended. Maybe Simon could have used some other wording but I think the meaning here is quite clear.

Simon Chambers

Thanks for this article, Simon! I’m new to your blog, living on the wrong side of the Atlantic to have come across you before the last month or so as I have delved into some British style podcasts.

Your article here reminds me a lot of the principles I use in teaching photography. You need to learn and understand the rules in order to be able to break them well, rather than randomly. I think it’s the same with style. You need to learn the basic lessons and have that understanding of them before you will be able to start to experiment with changing them for your own style. And then, over time, you will find what works best for you and continue to refine and experiment with that.

It’s how truly great photographers build their style, and I think it’s how sartorially minded men do it too!


Simon, on this leg of my clothing journey, my style is reflected in the pivot I am making in my professional life and augments my engagement with those who know me best. No better way to reinvent oneself than through fashion choices.

I have been dressing well for many years and conducted numerous audits of my closet. Admittedly, the pandemic has shifted my perspective on how I put myself together. But it has also freed me up from convention, giving me certain liberties, which I am enjoying. Nowadays, I find myself more forgiving of previous buying errors and am expunging pieces that “just aren’t me” anymore. I am also veering away (a trifle) from classic menswear and into more experimental areas of dress (at least, for me), introducing a ska vibe or a Neapolitan tailoring preference into the mix. This is what the style masters are showing, and I’m on board.

Post-COVID, I will be interested to gauge the response of clients, colleagues, and friends as I take these new looks out of the lab and into the physical world.


I don’t have anything of value to add regarding this article but I am curious about the shoes? They’re gorgeous, is there a post/can we expect a post about them?


I realise I should clarify, the two eyelet derbies.

R Abbott

Certain preferences are purely personal or idiosyncratic (e.g., favorite color), and others are highly contextual (e.g., what is “office appropriate” will vary dramatically depending on industry and location), so as you mention, absent a live in person conversation, people have to ultimately decide such questions for themselves. However, I still think it’s possible to do an even better job in presenting readers with information.

For instance, it might be useful and interesting to have an article about what sort of considerations people should take into account when choosing what to wear. My own theory is that it ultimately comes down to three factors: (1) whether the design or fit is flattering, (2) whether it is appropriate for the situation, and (3) whether it is consistent with the image you want to project.

To the extent you can touch on all three points, so much the better. So in regard to the first factor, I think it’s worth pointing out when a certain design or cut looks especially good on certain body types / complexions or conversely not as good on others. As for fit, you already have separate articles addressing how a sports coat or suit or other garment should fit. In regard to the second factor, you generally provide some coverage of this by describing things in terms of formality/informality. Given the diversity of cultures among your readers, that is probably the best approach. But it would be useful if you could do more in terms of the third factor – i.e., explaining what type of look or image a particular article of clothing or accessory helps conjure up, and to the extent that there are any negative associations, how to minimize those. However, it’s still worth doing, even if you have to be careful here (discussions about whether or not something is “appropriate” nor not can inadvertently trigger cultural flash-points).

I think you did this especially well in this regard in the article about white denim. You did a great job of explaining the pros (the color is versatile and elegant), the cons (they get dirty easily, the negative associations with “Mediterranean flash,” etc.) and how to minimize those (off white rather than pure white, not too skinny, denim more versatile than other fabrics, etc.). And you addressed this sensitively (e.g., by not writing in such a way that might be insulting). I’m not particularly sensitive myself and don’t like censorship (it’s impossible to avoid offending everyone and some people, who apparently have too much time on their hands, are almost looking to be offended), but believe that as a matter of politeness, people should avoid gratuitously offending other people. Just because you can doesn’t mean you should… But based on my experience reading PS, you’re very good at adroitly navigating these issues, so there’s no need to hold back.


Hi Simon,

I’m looking to build the formality of my outfits outside of wearing structured suits through the jacket and pants formality. With this, this leads me to two questions:
First, I was wondering what shoe styles and leather type combination would work with black as the leather colour as a nice middle ground in formality, as in it can be dressed up and down with ease?
Second, I was wondering if an OCBD, in blue or a small striped pattern, or a denim shirt without pockets and a knit silk tie is considered a nice middle ground in formality like the shoes? If not, what would be a middle ground in formality for shirting be?

Thank you in advance.


Thank you for your response Simon.
I was also wondering about the formality of the split toe derby as well as derbies in general, the double monk strap, jodhpur boots and chelsea boots since I like these styles as well and would like to understand where they can stand in terms of formality.
Also, would grained calf leather bring down the formality of the different styles of shoes and boots above as well as the loafer?


How does the formality of brown calf compare to black hatch grain leather?


Hi Simon,
I was wondering what parts of the PS lighter everyday denim shirt smarter than other denim shirts you can find shopping elsewhere?


Hi Simon

Bit of a tangent here, but I find the comment that readers might be Indian “going by their name” quite offensive, and I think you should consider removing it.

A few thoughts
1. India is a huge and varied country of over 1 billion people. Even if the post origin was relevant for things like familiarity of tailoring, cultural context, or climate, the generic “India” simply isn’t that useful.
2. The Indian diaspora is vast. Many of those with Indian names have been born in Europe, the US, Africa, or South America – and feel just as British/French/American/whatever as anyone whose name is not originated from elsewhere. For those in that situation, the everyday racism of assumed “otherness” is very wearying. At best, it’s lazy. At worst it has concrete effects on well-being, social integration and mobility, and even employment.

You are a gent and very obviously a nice person – I’d be grateful if you would consider changing this stereotyping sentence, as it will make the article more inclusive and welcoming.

Thanks for considering.


Hey Simon
Love the example of the daybreak trainers here, and also saw you recently checking out some nice vintage nikes in Sheffield. Any styling tips on what to go for here? I’m imagining something like these nike waffles might be slim enough to work well witgh chinos/oxfords/knitwear, or chinos/polo.

Is it best to go for something obviously birght/garish? this kind of thing?


this is super helpful thank you simon.

any principles for what works with what? I can vaguely imagine that a palette of muddy olive chinos and a navy jumper might not work with a flouro pale green, but would (for some reason i can’t fathom) work ok with either navy/white or bright red/white. Can’t quite pin down why. Is it an “opposite coour wheel” thing