The three wardrobes that define my week 

Wednesday, September 14th 2022
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Broadly speaking, I dress in one of three ways during the week. They are defined quite clearly (to simplify the process, as much as anything else) and represent three general levels of smartness.

I know readers will be interested in having these set out, as capsule wardrobes are always popular. 

But I’m also aware that all three could represent office wardrobes for some people - whether it’s a case of being smart but not wearing a suit, or of adding subtle touches in an environment where everyone wears T-shirts and trainers. 

So this could easily be another ‘Which office are you’ article, and just as helpful. I can expand any of the three into fuller lists of clothing (and sellers) if helpful. 

1. Jacketed

During the working week, if I go into town I nearly always wear tailoring. 

This is both because it is appropriate - it is what is expected of me, and the impression I want to give - and because I enjoy it. I love my tailoring but the most I’m going to wear it is three days a week; I don’t want to miss the opportunity. 

The tailoring is more casual than when I used to work in an office, in the City. It is mostly a jacket and trousers - rather than a suit - and rarely a tie or pocket square. But it is still smarter than 99% of people around me. 

I also wear more brown, white and black than when I was in an office, with those three plus shades of grey usually making up my jacket, shirt and trousers. The outfit above with my Pirozzi dupioni is a good example. 

However, if you work in an office this could just as easily include business colours, most obviously as navy. As set out in the five jackets article, a navy, oatmeal and grey jacket would go a long way. Combined with some of the five smart trousers and your regular shirts.

Top: Shirt, or at the most a collared knit

Bottom: Flannels, cords, high twist wools

Outer: Sports jacket

Shoe: Leather or suede, tending towards smarter styles

2. Casual chic

This is a step down in smartness. Usually worn during the working week when I’m not in town (central London). 

I mentioned during discussions about dressing during lockdown that wearing a shirt makes me feel like I’m at work, and should be working. It’s a motivational thing: I just never work the same in shorts and a sweatshirt. 

This second category is in that mould. It is smart, but it’s not tailoring. The top is collared, but the trousers are not jeans. It is the area of menswear that I’ve referred to as ‘casual chic’ and I think has the most potential for the modern man - but in many ways is the hardest to do.

Why? Because it depends so much on subtleties. It’s less about wearing a jacket or not and more about wearing smart chinos rather than workwear ones, or wearing a knitted polo shirt rather than regular piqué. 

The item I reach for most often here is my Rubato chinos. A pair of those, plus a shirt or smartish sweater (like the Cashmere Rugby) and a pair of suede or cordovan loafers, and I’m done. 

The smartest I’d go with trousers is flannels, but it’s usually chinos or cords; the most casual I’d go is ecru jeans. Outerwear could be a suede blouson or a long raglan. 

This category can also step up or down sometimes. It is, for example, what I might wear into town if I didn’t have any appointments. And it’s what I would wear to something smarter at the weekend, like a friend’s birthday party. 

Top: Casual shirt (oxford, chambray, denim) or smart polo

Bottom: Smart chino or cord, occasionally flannel or white jean

Outer: Cashmere knit, blouson, raglan coat

Shoe: Loafer or boot, suede or cordovan

3. Workwear and sportswear

This defines my weekend. There might be the occasional exception or simple laziness, but this is how I usually think when I get up on a Saturday morning.

Trousers: workwear chinos or jeans. Top: T-shirt or oxford shirt, maybe a chambray. Shoes default to tennis shoes, a canvas trainer, though with the occasional loafer too, as we’ll discuss in a moment. 

This is where my Real McCoy’s sweatshirts live, my beloved old Armoury chinos, my vintage outerwear and leather jackets. 

It’s obviously casual, but it’s also heavily influenced by the Ivy take on sportswear - by old, more considered sportswear. And by smarter takes on workwear too. 

In practice this means I’m often working slightly smarter elements into the outfit. For example if it’s a sweatshirt and chinos, I might wear cordovan loafers instead of tennis shoes. Just to keep things interesting - to avoid everything sinking to the lowest common denominator. 

Another example: an oxford under the sweatshirt rather than a T-shirt. Or with a T-shirt and jeans, perhaps a luxurious-looking suede bomber rather than a vintage varsity jacket. Both are beautiful, but in very different ways. 

This third category is something I’d suggest to a reader whose office is a sea of big T-shirts and Air Jordans. Try just tweaking one thing: old trainers, but with a blue oxford shirt; a T-shirt, but with Alden penny loafers; or a shetland rather than a sweatshirt.  

One step of elevation, but no more. Otherwise it looks like you’re looking down on everyone.

Top: T-shirt, oxford, denim

Bottom: Jeans, fatigues, workwear chinos

Outer: Sweatshirt, shetland, vintage military

Shoe: Canvas trainer, suede or cordovan loafer/boot

With all three capsules, there will of course be exceptions. I still wear a suit; I still wear a tie. Sometimes I wear jeans with jacket, or workwear into town. But they are specific exceptions with specific reasons - these three are the starting point, default.  

Here are some more images by way of illustration. But please, please read the text as well - otherwise like the piece on My Ivy, half the comments will be misunderstandings. These are merely intended to illustrate what is set out above.


Casual chic:

Sportswear and workwear:

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Dear Simon,

What a great article! This comes just at the time that the often repeated New Normal is coming into play. My Office habits have changed completely and thus, I believe, the “casual chic” will be what I will be aiming for. Even though I love my suits, opportunities to wear them are getting more scarcer.


Tommy Mack

Lovely stuff, Simon. I tend to fall into a similar pattern: Casual chic if I have a lot of in person tutoring, workwear but with an Oxford or knitted polo if it’s mostly online and generally some little twist to lift my look above the absolute basic even if I’m not working.

Sadly, I rarely get to wear tailoring these days, a trip to the theatre or a decent restaurant maybe (not just Pizza Express with the kids!)

I’m definitely on the lookout for casual blazers/sports coats (linen, hopsack, flannel, canvas etc. Tweed even) I guess a sort of inversion of casual chic: giving my appearance the boost that comes from a tailored jacket but something I can wear out with the kids and not look overdressed/worry about it getting ruined!

Tommy Mack

Yes, definitely. Relaxed Ivy casual feel!


Cord jackets? Took the plunge this year got one in brown. I have found it really flexible – works well with jeans, most chinos and workwear but also with flannels.


I’m very tempted to dig out my old cord jacket from the dark recesses of my wardrobe. It’s just a pity it is quite a pale shade.
I still have patches on my tweed jackets.


Yes, I am a history teacher so perhaps I lean into that a little. That being said, I think the cut can help. Soft shoulders, 3 roll 2 and a slightly higher gorge can help avoid that fuddy feel to some extent. Elbow pads are obviously out!!

Tommy Mack

Yes, I think with a jacket and chinos, I’d stick to knits or very casual shirts like chambray, never something even as formal as an Oxford. (Unless I find myself teaching in the classroom again!)
Also, I figure never blue blazers or mid-beige/grey chinos to avoid the preppy business-casual look. Brown, olive or (dark) grey up top, olive, brown, stone or even black chinos below: those ever-wearable cold colours once again!
Thanks for all the pointers everyone, I’ll bear them in mind!


For a reason I don’t know, I struggle to pair chinos with jackets. I always feel the result is awkward. I love pairing Harris Tweed with jeans, but I don’t feel it work with chinos, for instance. The only exception might be with Hopsack jackets. I manage to decently pair a navy blue one with olive or stone chinos, or an oatmeal Hopsack with navy or dark brown chinos. Other than that, I prefer to combine chinos with denim shirts with or without knitwear (ideally with a chunky shawl collar cardigan). 


Such a good point. I find exactly the same. This seems to be something to do with the garment washed nature of the cotton, since ecru chinos look so much less satisfying with my wool jackets than ecru denim or ecru wool options. I recently tried some denim-style cottons and basketweave cottons that had none of these issues, so I think it is a particular thing about the subtype of cotton (and maybe it’s flat, washed-out relaxed sense) rather than “all cotton”


Casual chic, and entirely because of PS, is now my usual wear – elevated from my lockdown work and sportswear. Again, I’m finding it successful to incorporate both black knitwear and my (over) large collection of shirts. As you say, the step up or down makes it so flexible.
Smart chinos are rapidly becoming the Swiss Army knife of mens’ clothing.


In the first casual chic article, you quoted the importance of seeing each item separately and moving them around as needed.
Could you do more on this, Simon? I think it’s one of the key ideas and I still struggle with this.


Hi Simon,
Agree – great article.
That blue suede jacket is fantastic. May I ask where it’s from?


Thanks Simon – sadly not in their current collection. I thought it might be your new PWVC reversible suede blouson…


Really enjoyable read. I wonder how you’d conceive of your approach to dressing for the evening, and whether variations on categories 1 and 2 would be the ballpark? I personally find it easiest to wear tailoring and suits at night these days – something to do with the clear ‘pleasure’ rather than ‘business’ context, and maybe even a social expectation now that it’s more expected to dress up a bit for a restaurant or party than for work.

Phil McAvity

Dear Simon
Would it be acceptable to wear a bottle green cardigan with a blue oxford and cream chinos? If so, what footwear would you recommend? Thanks


This seems quite close to what I find myself wearing (no doubt influenced by years of reading PS), though more jacketed looks and fewer non-ecru jeans even for the casual outfits. Not having a house, nor children, reduces the need for durable workwear quite a bit.
I’d say the “cold color capsule” might be the best article on PS, simply because the color schemes there makes for so many outfits that are clearly stylish but do not feel corporate or stuffy. While soft tweed jackets in brown, cream flannel trousers and brown suede shoes will most likely be smarter than most people around you, it’s hard to accuse it of being “dressed up”, and as long as the cut and silhouette is flattering it probably won’t look overly stuffy.


“One step of elevation, but no more. Otherwise it looks like you’re looking down on everyone.”

Are you sure about that sentence? I doubt anyone would think that. Wearing a suit to a barbecue is one thing, but a shirt and loafers? It really doesn’t feel like too much.
Otherwise, great article!


its interesting how everyone gets to dress as (badly as) they like, but if you dress as you like with a suit you are the one committing the crime


hi Simon, very helpful article: like the 3 outfits in the reader profiles, but with the categories more defined. My wardrobes are (a) suit in wool gabardine, cotton, linen or flannel usually in non-businessy colors for days when I have meetings (b) similar to your jacketed for workdays when I don’t have importants meetings and when I go into the city at the weekend, and (c) sliding scale of your casual chic to sportswear for the weekend when I’m not in the city.

Workwear is the one area that I haven’t been able to successfully incorporate into my wardrobe, apart from jeans which I suppose one can’t really call workwear anymore. I’ve tried a number of times but workwear chinos, sweatshirts, work boots are all part of an aesthetic that doesn’t feel like me and I’ve decided to drop it for now.


I found the latest article on Die Workwear very useful for helping me to think about and explain why I like some of the looks I like, and why I don’t like others.
I am sure most readers have seen it but if not it’s worth a read:
The tip at the end of the article on starting with an aesthetic I found particularly helpful: workwear really isn’t an aesthetic that I am drawn to or relate to. I think for that reason it always felt quite forced whenever I tried to wear it, and after enough experiments that didn’t work I decided to leave it to other people who do it much better.

Joe P

Really good piece, Simon, and I think you’re spot on about the interplay between the three. I work in book publishing and my own office/industry is an interesting mix of all three of these paradigms.
Tailoring – as in a top-to-toe smart outfit – seems to be reserved mainly for events; for a meeting most men just throw a jacket on over their Oxford and casual chinos. If you wear a sports jacket “just” to the office it tends to draw comments; not negative ones but it’s noticed. In fact, just wearing tailored trousers stands out!
I like dressing smart/making an effort – especially since such a prolonged period of working from home – but don’t want to look too incongruous (I also simply don’t have enough jackets to wear them each time I’m in!). So it’s about finding a balance: I’ll wear tailoring if I have an event or external meeting, but I think you’re absolutely right about casual chic offering so much potential, and it’s roughly the look I’ll tend to aim for most days. Though I’m still “learning” it and maybe often end up somewhere between the two more casual looks – which is probably the worst of both worlds!
On the Rubato chinos: I’ve been considering a pair ever since you first reviewed them, as I’m lacking a versatile smart chino. But of course you had them slimmed, something I’m unlikely to do. Do you still recommend them to people who would keep them as they come?

Joe P

Yes, I think those tweaks are where some of the interest can lie. For instance this evening I’m going to the leaving drinks of a much-liked and senior former colleague: I plan to wear a Drake’s jacket that’s mainly earth tones, with small navy and dark green checks; a brown Anglo polo; Drake’s ecru jeans; and brown suede Alden chukkas. The jeans are probably what will stand out to people in the context (not many white jeans in publishing) rather than the jacket, but hopefully they and the polo make it casual enough that the whole doesn’t shout too much. We’ll see!

Have you ever posted the measurements you tapered your Rubato chinos to? Everyone’s different of course, but I’m sure there are a fair few PS readers (like me) who are similar enough in size to you that it could be useful. Feel free to direct me to a post if you already have!


I believe the hem width in the original post is incorrect. Should read that the hem was reduced from 22.5cm (not 20.5) as correctly described in this post
Hope I got that right?


Somewhat ironically, a well-cut bog standard worsted wool suit fits all three categories. One can simply dress it up (with a tie) or down (with jeans). Anecdotally speaking, one would fetch a lot more attention in any of the above outfits posted by Simon as compared to even a chalk stripe structured 2-piece suit with peak lapels. Unfortunately, hardly anyone (except us aficionados) wears tweed/silk sports jackets anymore and therefore it is harder to blend-in. For a more visual interpretation, see Daniel Craig’s wardrobe in Layer Cake.



100% agree. When I wear a suit (and/or tie), I get immediately asked whether I have a court hearing that day (and I do the same with others, I have to admit).

Peter K

Yes that’s exactly the question I get, even when I wear a suit with loafers and a polo shirt. I usually reply with something like “What’s the point of owning a nice suit if you never wear it?”


I work in IT, in a company that emphasises they have “no dress code”, and I have gotten one or two comments at the beginning, but now the people are used to the fact that I might come to the office in a full suit, jeans and a t shirt, or anything in between. I think if you never do it and one day appear in one, people will comment on it because it’s something new. But other than that people do not care that much about what you wear (at least here in Denmark).
We even have a company photoshoot coming up and we were encouraged to wear what we wear everyday, instead of trying to make everyone look the same.


A timely article. In the Casual chic category, would the Civilman trousers mentioned here work?
I have a pair in taupe.



Another most helpful article Simon, particularly for me at the start of my style journey. Thank you.

Bob M

Thanks for this timely article.
For the last year, I have been overhauling my wardrobe. Ex corporate, I no longer needed the dozen suits and other tailored clothing.
It just so happened that my wardrobe as evolved to exactly what you described: chinos and Luca Avitable shirts during the week, jeans and a sweatshirt on the weekend, and for evenings out … grey slacks and a blazer. Easy.
Now, not only is my wardrobe an order of magnitude smaller, I’ve been able to upgrade the quality across the board.
It’s refreshing to hear that it is all worthwhile!
My only remaining struggle is knitwear for the chinos. Any thoughts on turtleneck vs. crew? I’m thinking of a dark navy cashmere ribbed fisherman’s sweater but can’t decide on the collar. Any thoughts?


It would be lovely to have a covering of brands in the ‘casual chic’ theme, as I find it the most difficult to shop for. Maybe there are already articles on PS Simon ?


I believe this is one of your best piece yet regarding how to dress depending on formality. It allows one to have a better grasp on the whole spectrum from smart to casual with interlinks between each category to better modulate the level of formality hence accomodate to the best our personnal work life.


Indeed Simon, i have read both that one and the one on colour combinations which are very much cartesian in nature, almost scientific the way you treated them. I do believe that to grasp a better idea of subjectif elements like clothing styles and their in-between, “bouquets” of lookbook photos with few or any words at all, like you have done here, are much more suited.


Dear Simon,
a very interesting article. 
It’s no different for me, although as a lawyer I also regularly wear a more formal suit and tie when I have hearings or meet rather conservative clients (but not for a regular day in the office).
Most interesting is your statement that you should not dress two categories up from everybody around you. I think this holds true but is sometimes difficult when you do not know how everybody else will be dressed (e.g. a banker turning up in jeans and a white polo).
Everything is in flux right now and the new normal has not yet been established, I believe. I can see this in my own wardrobe where until ten years ago I had around 10 suits (grey, anthrazit and black) and now I feel I barely need three.
Kind regards


Another great article with nice fotos too. In my opinion the jacketed style is your style. You have many many great bespoke things and you are experienced enough to combine them like very few. The casual chick style is the most interesting one since you can drive it up and down but i understand what you mean that its difficult. The sportswear is for me where the style just doesnt look so fine. I respect ivy roots but to be honest in this category its more important to me how the person phisycaly looks( hight, age, body condition etc). I have seen guys rock the sport style but more because they were people who do a lot of sports for years, noone fat, short, old would look so good in this category.

Paul H

Great piece Simon! This is the first I’ve noted you mention owning Real McCoy’s sweatshirts. Would you mind elaborating on what you enjoy about them and what separates them from others (e.g. your Merz Schwanen)? I’m aware of the great quality as I have some of their tees and a few items en route, but have yet to try their sweats.


Hi Simon, can i ask which of the Real McCoy’s sweatshirts you wear. There are so many different varieties on line!


I always find these pieces so thought provoking or a place from which to draw inspiration. Or something with which I identify or refine my own tastes. Interestingly, I found this only thought provoking, but oddly alienating. Going to try and articulate why as I think you might find it interesting.
Firstly the matter of personal taste… I find the kind of Rubato flavoured ‘casual chic’ particularly hard to pull off as you identified it being. I think it’s so particularly dependent on the fit. The muted tones and stylings are only chic if everything fits perfectly and there’s no veneer of dressiness, style and/or ruggedness to hide behind if it doesn’t. You wind up looking like a golfer or a chartered accountant on casual friday if you get the fit part wrong. Still for me and my tastes, I avoid the casual chic category because it seems neither here nor there. I like combining modes of formality in a way that subverts something or if not doing that, then just being sincerely being quite smart, or quite casual. This form of casual chic always seems to be somewhat on the fence, like I’d always be overdressed or underdressed but never quite right. Maybe it’s an age thing. I’m 28 and look at those outfits and have absolutely no idea where I’d be going dressed like that. Perhaps that will become clearer as I get older and I get invited to things other than the pub.
Secondly and I guess this is basically taste too, as it’s all personal isn’t it, but I find how I dress is almost always opposite to your functional categorisations. I’m sat in my office in Victoria writing this, wearing blue jeans, white canvas trainers, a white t-shirt and a blue chore. I could stand to be smarter for work, but because I dislike my job, work flexibly, care very little about my colleagues but would generally prefer their opinions about me not to be too strong, that I feel least inclined to put effort into my clothing on days that I go in. I reach for something easy, functional and unassuming. Clothing that is hard to project assumptions or preconceptions onto. Flying in the face of your categorizing, I often get smarter after work. I’ll take off the trainers and put on suede boots, remove the chore and add a sports jacket and then head out for the evening.

Lastly, I find that a jacket is more versatile than you’re giving it credit for. Yes, fewer people wear them nowadays. But I venture that it’s this: fewer people wear them well. Broadly, the men interested in clothing shop at Mr Porter and End and are largely wearing streetwear and workwear. But there’s still no shortage of men wearing ill-fitted suit jackets with baggy blue jeans and shiny black lace up shoes still out there wreaking havoc on good taste. There’s still also legions of men wearing Drake’s Games Jacket-esque jackets out there in london, worn ironically with joggers etc or earnestly with chinos. When I get into a nice sports jacket worn in a vast number of ways, I don’t feel totally overdressed. Usually because I’d be doing something to subvert it. A western belt and RM Williams boots. A t-shirt and jeans. High waisted, wide legged trousers (casaatlantic or civilman trousers). It feels dressy and tasteful but also a bit subversive. All the more so now there are more guys wearing plastic sliders and white-socks out in soho on a friday night. Without sounding too much like a delusion of grandeur, I genuinely feel like I’m doing my bit for menswear by not kowtowing to the prevailing consensus that the closer to loungewear you are the better. When I was in my early 20s, most of the sartorial decisions I made were based on what I saw people wearing in public. The more people wearing sports jackets well, the more people will.
Apologies! I started this as simply a comment and sharing a personal response and it became something of a manifesto


The pity is that even though suits are rarely worn today the present style of suit exemplified by yourself with soft shoulders,SB and slim trousers with no break is my favorite of all it’s iterations.

Eric Michel

Very interesting, and I share many of the views in this article. I would just add that seasons play a role in this game: casual/sport is much easier to manage over summer with a pair of loafers worn bare foot to soften anything too casual. A serious French newspaper published a long article few days ago which title was : “Are loafers the new sneakers?”. And I would just add that in winter, I wear a lot of cashmere turtlenecks, which ultimately play the same role than loafers in summer: they look smarter than a hoodie with a jean, and more casual than a shirt with a jacket. But you need to be highly selective as the wrong fabric and style will convert a turtleneck into a real “faux-pas”…


Hi Eric,

I’d be interested in reading the article if it is online, do you have a link?
For me loafers are definitely the sneakers of other people; I only own a pair of Adidas Barricades which I don’t wear outside the tennis court, so in summer it’s loafers with everything, and in fall/winter those are replaced by Chelsea boots.


Hi Simon, with so many of your readers no longer in a daily environment to wear 1. Jacketed. Do you have any advice on how can wipe the dust off what were, our very versatile dark brown oxfords?

Very nice post and great pics.  


Nice suggestion, thank you Simon. Looking back (2008 to 2018), rotating a dark brown and black Edward Green Piccadilly, would have been close enough in formality as brown oxfords. And they slot in nicely for today’s modern man 2. Casual chic

Perhaps the Oxford, worn more casually, requires the influence of fashion. 


A very helpful piece. But I am still struggeling to unterstand the difference between a category 2 and 3 chino. Is it the colour that sets them apart, or the cut, or the fabric? Could you elaborate, please?

Srivatsa Marthi

Simon, even though this approach is embedded in your other articles, I found this one in particular very useful. Nice to have it laid out so crisply and clearly! One question: what are your ‘Outer’ layer equivalents for summer? I know for Outfit 1, it is linen, silk-wool-linen mixes, etc. But what about Outfits 2 & 3? (This was something I struggled with this summer.) Thanks again.


A very good article. Interestingly the office where I work (in the City), has just sent out a e-mail to say that staff thinking they can keep wearing trainers (with their suits), can’t. We are, in effect, back to 2019 dress standards (without the ties). I feel a lot of financial services companies are pulling back on relaxed dress codes. I remember this happening before after the 2001 dot com bubble and relaxed dress in offices.


As always, great article, Simon. This article answered the question I asked you yesterday.

So, I guess I need to wear more casual chic. I would wear the raglan coat for winter, but in the autumn or spring, would casual jackets such as Drake’s games blazer in corduroy or The Anthology’s lazy-man jacket work?

Many thanks,


Thanks, Simon.
Do you think wearing too formally to informal settings could be similarly inappropriate as wearing informally for formal settings?
For instance, a college student wears number one (jacketed) to lectures while the others wear number three (workwear/sportswear) hoodies/sweatshirts with Air Jordans. And a company’s manager wears number three (workwear/sportswear) while other colleagues wear number one(jacketed).

Ian Daly

Hi Simon
I’m somewhat confused by the title of this article.
Surely outfits don’t define your week? I would have thought your week defines, or determines, your outfits?
Maybe I am being overly simplistic, but what you are doing determines your choice of clothes. You seem to be saying something opposite.
If I’m gong somewhere smartish, I chose smartish stuff to wear, and so on.
So your activity defines your outfits.


This is an excellent and very helpful article. To me, there is a common theme throughout tour categories and choices…simplicity. I’m old enough now to realize, after many sartorial mistakes, the truth of Cary Grant’s statement that simplicity was the essence of good taste. As result, PS articles like this are very useful to read and reread as they help me fully incorporate the simplicity principle and enjoy the process.


is there a reason that in category 1 you say you aren’t wearing pocket squares and yet every photo with a jacket to illustrate has a pocket square?

whilst I know the answer it would still be great if an article could cover the trouser options (eg flannel) for those of us where £200 is a stretch target


I appreciate that and that your own suit supply days are now long behind you… not all of us have moved on though.

Thanks to everyone else for the suggestions. SuitSupply I find wear out very quickly but will look at some of the other ideas

Peter K

I have a pair of flannel trousers from Spier and MacKay that I am quite happy with. They currently cost around CDN $178.


yeossal (benefits is mtm, but they have rtw too). natalino (if you’re built like a matchstick). and I guess spier and suitsupply. (I’m not sure if spier high rise is actually high rise, I have slim shorts and they seem normal or even low rise, but I’m about to order a contemporary pair to see if that will help). unless I want to match trousers to jacket, I’d always order trousers and long sleeve polos from yeossal. shoes, maybe, and I haven’t tried other things.

and if you’re on super budget, can’t beat tk max (but there you trade time spent looking for stuff for money). Ralph Lauren chinos, Lewis jeans, sometimes brooks brothers chinos.


@Bob: I also do not like to go beyond EUR 200. The best trousers for me that I have discovered in this price range are Cavour (on 50 percent sale) and PT Torino (also on sale), which are quite often with these two brands. If you like the style also Pini Parma and indeed Suitsupply are not bad.


Dear Simon

In a previous fairly ancient article, you suggested not to combine a white oxford with jeans and a blazer due to the wrong level of formality.

Have your thoughts evolved on this, and is a white oxford excluded from category 3 (including the PS Oxford which hopefully will return to stock soon!)?

J. Vantaa

Here with my two cents again.

I quite often play with “the levels of formality”, but there’s a slight tightrope walk here; you have to make it clear enough that it’s intentional, but subtle enough not to break the whole ensemble.

I’d wear a solid coloured flannel shirt with suit and tie for example to add little sartorial mischief, but plaid one would be way too much. Then again white oxford in certain instances could be little too close to more informal shirts and might be seen as a mishap more than considered choice.

Do call me out if I’m flagrantly wrong.


casual chic is what I am aiming and interested in with a further interest in Japanese style workwear for weekends. Although I could wear my tailored jackets to work, no one else wears them making it a bit harder. I’m thinking brands like Stoffa, and making tailoring materials into casual jackets. I have a field jacket in very dark brown flannel (similar to your char brown fox flannel) from Loro piana which I find works with grey trousers as well as navy, tan and olive chinos.


Great article (and outfits). Can I ask where the grey skipper collar knit is from?


Hi Simon,

A good read, thank you. I haven’t been a PS reader for that long, but I have certainly enjoyed observing the evolution of your personal style, and how it got you to this point. I have undergone a similar personal journey in a small way, no doubt inspired by what I read here.

May I ask an entirely unrelated question: how do you look after your flannels? My understanding is that no flannel is machine washable, and for me that has always been a deal-breaker (my trousers seem to get dirtier than everything else, and in my belief there’s no substitute for passing water through the fibres, no matter what they say about dry cleaning – a process I distinctly dislike). Otherwise, I’d love a pair of dark greys for regular use. Grey chinos aren’t quite right somehow.



Hi Simon – is pressing something you do at home (with an iron), or can you take to London dry cleaners and ask for wool trousers to be pressed? Sorry if this is a stupid question. Try to look after my new flannels


Simon, I see you have tucked in the white t shirt in the top picture. Is that a knitted t shirt and is there a rule of thumb re tucking in or not?


Just wondering how work short sleeve polos into category 3? Would you every wear a short sleeve polo on its own with jeans or workwear chinos when the weather is warm? Is a fully fashioned cotton or wool polo too smart?


Thanks, Simon! This is a really helpful and practical post. I think one of the things I struggle with most when trying to dress well is how to balance that will real life. I want to look sharp, but I don’t want to wear a suit to my son’s soccer practice. I appreciate the options presented here. Could you give your opinion on what makes chinos smart vs workwear? What features do you think separate the two? Thanks, as always!


Hi Simon, Thanks for the response! I happened to see that other comment after I sent mine. Sorry for the redundancy!


Hey Simon, a question completely unrelated to the article:

I’ve been wanting to make an overcoat in heavy cashmere for a long time, and today my tailor showed me a possible fabric: a very heavy (over 700g) cashmere that was surprisingly affordable (for being heavy cashmere). However, on closer inspection of the bunch, it turned out the fabric sample is two thinner pieces of cashmere layered and sewn together. Is this common? It’s listed as 750g, and only careful inspection showed that it wasn’t a solid, thickly woven fabric but two thinner pieces laminated.

Is this an established practice for fabrics this heavy? Would it effect the quality of the fabric. Especially considering the fairly low cost of the fabric, I’m obviously a bit worried I’d be getting an inferior product.


That fabric bunch does have a lot of double-faced fabrics (some interesting but mostly useless ones, like purple-cream). This particular one was the same color on both sides, but I suppose you could get a shinier material on both sides of the fabric by laminating instead of weaving a thicker fabric. I’ll have to think of it for a few days, and maybe look up the details on that particular mill.

I already have a back-up in mind, a thick, fluffy camel hair from Standeven. Thanks for your input!


This is a fantastic article and just so useful. Expanding on how to blend from one to the other is also useful. I suspect many readers now wear tailoring/jacketing options in evenings alone. What are the white trousers shown with the brown jacket and grey polo? Are those the officer chinos? Looks a great mix of casual chic and jacketed


This is brilliant – seems a successful example of cotton trousers that nonetheless work beautifully with a jacket. (Avoiding the worry about flannel or cavalry twill wools being a little too formal) Thank you Simon


In which category would you put the casatlantic el jadida?

A woman who loves to read about men's style

You illustrated the three styles quite helpfully here, Simon. At dinner a friend said her husband had trouble assembling a capsule wardrobe for a business trip to Japan. He works at Facebook and isn’t particularly verbal. The photos here are just the ticket, I think.

Rowan Morrison

With jackets like the brown leather one three pictures up, do you find you have to buy them a size larger in order to fit over a sweatshirt? Getting fit right appears to be a fairly precise art, so I find that a jacket that fits me well over a sweatshirt or jumper will look too big if I only wear a t-shirt or single thin layer.


Hey Simon, sorry to intrude but on that note, if you were buying your Chapal again, would you bump up to a size large?

I ask because I still intend on purchasing one at some point (black) however I’m a little between medium and large. I’m leaning towards large at this point given it’s already quite a fitted jacket and even possibly adding a cm or two to the body length. I’m a similar height and build to you for reference (slightly broader chest maybe).

I’m of a similar mind to you and have recently realised slim as possible is not always the way to go. This is exemplified fully after purchasing two of your beautiful tapered tees recently. That extra bit of chest room as well as shoulder breadth does wonders. Granted I wear slightly fuller jeans/trousers so it all balances out nicely. Is it worth tending towards these slightly fuller dare i say it more comfortable measurements? it’s a fine line of course I understand.


I started my career 20 years ago and our managers used to blame us when we did not wear a tie. Today, people in the office laugh at me when I wear one (while they believe they are dressing smart casual by wearing ill-fitting jeans, a white popeline shirt, a dark grey suit jacket and black oxfords). I can’t stop thinking something is going wrong. 
Your sentence “One step of elevation, but no more. Otherwise it looks like you’re looking down on everyone.” is absolutely spot on. The best advice about office dressing I’ve ever heard. 
Thank you again for this great post.


The particular outfit favoured by your colleagues remind me of the pseudo-manager uniform I saw in Sweden in the 2010s: Levis indigo denim, navy jacket (too short, too thin lapels) from Dressman, either a plaid shirt or a polo (Gant or Polo RL) and sneakers or tan-bordering-on-orange leather shoes.

I keep associating denim and jackets with that look…

Simon K

Now with less informal dresscode in the Office (tie and suit feels over dressed) alot hangs on the shirt so to speak. It is the garment where you can play around with many variables if you care about style and I dont want to go to knitted in the office. To me it gets a little tired and even sloppy if you understand.
I would enjoy very much your thoughts on how one can go about this.

Simon K

Thanks for the links!
Absolutely, trousers not less important. Its just that the myriad of choices for shirts feels overwhelmimg, especially as I would like to try something new.

Kudakwashe Wedulo

Hi Simon, totally unrelated, am considering purchasing a pair of black calf loafers from e&g, with R1 sole for winter. My question is, is the black shoe, black socks rule real?


That black socks only, for black shoes?


True. Thanks.

Rob H

Hi Simon

When you come into London as you describe above – how do you travel? I’m wondering whether the kinds of clothes in (1) can stand up to commuting by bike or by tube, and how they manage to still look so good despite the wear grind and sweat of everyday use

Rob H

Thanks Simon.
So the tailoring in (1) is robust enough for tube & bus commuting but not cycling – and a good idea to press and steam at home. Thanks!

I live in fear of destroying my nice clothes in the London mud and rain and in the hot squeeze and dirt of public transport

Guy Graff

Hi Simon,
This is interesting. What you describe here is my MO. As a real estate broker in a resort area (Hamptons LI, NY) going back to the ’70’s in my early 20’s (not today to be clear) this is the way I presented myself then and now.
Look forward to meeting you in NYC this Oct. which is where I reside.


Hi Simon, where is that grey knit/sweater in ‘casual chic’ photo from?


This article is really useful. One addition I’d make is that as an avid PS reader it’s quite easy to fall into the menswear bubble and forget the maxim that dressing well is partly also about what others around you are wearing. Sometimes trends in menswear are so usual that you forget that they are quite unusual around you. For me nothing epitomises this more than the tassel loafer. I made an error in getting these rather than plain loafers – too many noticing questions at work, and not in a good way! Rather like monkstraps 5-10 years ago – a sign of the “iGent”. I’ve since gone with plain loafers and am far more comfortable!


useful to have it all laid out, and yes you’re right re dressing just one level above those around you. i have wardrobe full of worsted suits as i work in finance. but the shifting paradigm means i can just about get away with grey worsteds and an open neck. so i wear them as much as possible before they become obsolete too. any suggestions how i can ‘soften’ my navy worsteds and bring them back into rotation?

Anthony March

So glad to see the skinny look gone,was never smart

Dimitrios Rigas

Hi Simon and thank you so so much. I work here in Athens and often struggle to work out what to wear when I travel to London or Berlin on business. It’s also complicated by varying climates. Your piece helps those of us who want to look professional but not as if we try too hard. Thank you and best to you and all the PS community. Dimitrios

Nils W

Hi Simon! Great article as always. Where would you put your trousers from Casatlantic on this scale? Are they equivalent with the Rubato chinos or do they belong in the last category?


Hi Simon, fantastic article as always. Would you be able to please help with some recommendations on M2M work shirts at the c£100-150 price point? I’ve tried some of the online companies with mixed results, so would really appreciate any input! Thank you


Hi Simon
What do you think of this dark brown cashmere for a jacket

Do you think it’s a versatile pick for a cold colour capsule? Could it work just as easily with jeans?


Thanks Simon!
I believe it is a very light weight – 11oz or so. Would this work as a 4-season year round option?

Amrinder Saraogi

Simon! I have a question regarding the point where you mention about adding one smart element in the outfit.
Could adding a polo t shirt instead of a tshirt elevate the outfit?
For example wearing a polo t shirt instead of a t shirt and wearing the same with jeans and a trainer?


Hi Simon, my brother has started working for a high end gym in London in the sales team. He needs something smart casual for work. I thought corduroy would work but perhaps it’s a bit countrified? He is looking for something of good quality under £200 that will work in a smart casual work environment. The issue I’ve found is that a lot of the brands are a little to old school, he’s 28. Any recommendations thanks


Hi Simon,

Thanks for the article, how often would you say you take out your suit and tie these days within the month?

And if you were someone starting out on bespoke tailoring would you suggest a start on jackets rather than full suits?



Thank you Simon, would you say that bespoke tailoring then is really “dying” out given that even someone such as yourself it seems is wearing less and less of it.

I remember an article you wrote on “we will survive” I wonder what are you current thoughts and what you see in the industry trends in surviving post Covid.



In the last photo, wear are the khakis from mate?