Which sports-jacket office are you?

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One of the most popular posts we’ve ever written on Permanent Style was ‘Which office are you?’, back in February 2016.

It showed a spectrum of outfits from T-shirt and jeans, through knitwear and flannels, up to a jacket and tie - with just one piece of clothing changing each time.

The idea was to demonstrate how such changes affected formality – and therefore how any reader could pick the one that suited the dress code of their office.

This post builds on that concept, but within narrower bounds.

Here, we take what I hope to be the future of professional office wear – sports jacket, shirt and trousers – and demonstrate how similar changes affect formality.

So we start with the American classic - navy blazer and grey trousers - and push it through paler colours, hairier textures, and different trousers, all the way down to tweed and jeans.

It is a more focused ‘Which office are you?’ The kind, in fact, where everything could be relevant to the same office, going from client meeting, to every day dress, to perhaps dress-down Friday.


1. Navy jacket and grey trousers

This first combination is so ubiquitous it is sometimes referred to as the ‘menswear uniform’. But frankly, unless you spend your time at Pitti or in a menswear store, it’s more likely this will be associated with a certain gold-button-blazer American type.

Ignore that and try it. The combination looks so much better than a suit without a tie, and if well made and well cut, it will look smarter too.

The trousers can be a high-twist wool in warmer weather or flannel (as here) in colder.

The handkerchief makes it a little stylised, and you could start without it. Perhaps even just to add when you go to dinner in the evening.

Jacket: Navy mesh from Holland & Sherry, made bespoke by Ettore de Cesare

Trousers: Mid-grey flannel from Smith's, made bespoke by Edward Sexton

Shirt: White-cotton twill, made bespoke by Luca Avitabile

Shoes: Brown-suede oxfords, made on an adjusted last by Saint Crispin’s

Socks and handkerchief: Cotton and linen respectively, from Anderson & Sheppard


2. Oatmeal jacket

In outfit number 2, we swap the navy jacket for an oatmeal-coloured cashmere one.

Changing from navy or grey is instantly more casual; but the oatmeal is still quite smart, due to its cold, muted tone. It sits perhaps halfway between navy and a stronger green or brown.

The cashmere fabric also means the jacket sits between those two, being not as sharp and crisp as hopsack, but smoother and more luxurious than tweed.

The overall look is still fairly formal, with its restricted palette and lack of pattern.

The shoes, by the way, we are keeping the same throughout every outfit: a brown-suede oxford.

A leather shoe, in particular a black one, would be smarter and probably more appropriate with the first outfit (especially given the contrast laces).

But suede still works. And keeping the same shoe throughout allows us to focus on just the jacket, trouser and shirt.

Jacket: Oatmeal Loro Piana cashmere, made bespoke by Elia Caliendo


3. A blue oxford shirt

This is the most subtle change of the series, and has greater impact in person. But it’s an important one.

Most men think of blue and white shirts, in a variety of patterns, as interchangeable. But a plain white cotton-poplin is much smarter than a striped blue heavy-oxford, as shown here. The first is very corporate and professional, the second rugged and casual.

There are three variables, and they all make a difference: colour (warm/cold), fabric (smooth/rough), and pattern (plain/not).

Other parts of the design can also make the white shirt more formal: a lack of placket, a non-button-down collar, even the height and angle of the collar.

Perhaps most obviously, the shirt makes it much easier to bridge into the next change, which is one of the biggest.

Shirt: Blue/cream stripe PS Oxford fabric, made bespoke by Luca Avitabile



4. The tweed jacket

Hopefully by now readers will know to look at this jacket from the point of view of both colour and texture. The brown is stronger and warmer than the oatmeal it replaces; the tweed is rougher and more varied than the cashmere.

The whole outfit is now much more casual, and is perhaps one no lawyer or banker would wear to the office. But a fund manager or tech executive might.

Indeed, during a talk I gave two weeks ago, one attendee said in his area of tech, the uniform was pretty much jacket, polo shirt and trousers. His question was, how to do it better. I’d point him towards this outfit, plus numbers 3 and 5.

At this point the white-linen handkerchief is also verging on too smart for the outfit. A wool/silk or cotton, with more colour and pattern, might be better. But as with the shoes we’ll stick with it for the sake of simplicity.

Jacket: Holland & Sherry tweed, made bespoke by Elia Caliendo


5. Chinos rather than flannels

Arguably, the trousers make a bigger difference to these outfits than the jackets. The change from flannels to chinos to jeans, is more extreme than worsted to woollen to tweed.

That change can be felt immediately here. Even though the cotton trousers are fairly trim and smart, they don’t feel like traditional office attire any more.

Tailored cotton trousers to wear with a jacket are not an easy thing, largely because of the cottons offered by most mills (in my experience). But these from Stoffa do it well. More on them in a week or so.

Trousers: Stoffa exclusive plain-weave cotton, made to measure by Stoffa


6. Swap chinos for jeans

The final change, and the obvious one. It doesn’t get any more casual than this, unless you want to explore rips and cargo pockets. Which we don’t.

These are of course my bespoke Levi’s jeans, which have done great service over the years (though now a little tight in the seat and thighs).

They are a blue Cone Mills denim, heavily worn and therefore lightened. Newer, dark-indigo denim would be smarter and easier to wear with tailoring.

But these are just about OK, largely thanks to the casual pieces that have been added during this process: the shirt in a traditional, slubby oxford fabric, the jacket in a Harris-coloured tweed.

The oatmeal jacket from earlier would struggle to work with these jeans, as would the white shirt.

The latter would need everything else to be casual: that same PS Oxford texture and style details like the placket and button-down collar; even a breast pocket.

Jeans: Cone Mills denim, made bespoke by Levi’s


That’s the sliding scale of formality. The modern office outfit of jacket and trousers, in six different combinations.

Links to all the clothes featured (including cloth numbers, for example) are in the links at the bottom of each numbered section.

The only question is, like last time, which office are you?

See the original article here.

Photography: Jamie Ferguson @jkf_man

What to know more about how Permanent Style is funded? Read here

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Hi Simon, A great article and I was one of those who really enjoyed your Which Office are you? post.

My question would be with relation to seasons. You have cashmere and tweed in the more casual outfits seen here which I would associate with the Winter. What could be worn in Spring and Summer? A linen/wool/silk combo jacket to replace the harris tweed here would be nice, although maybe not with jeans for me… What alternatives would you suggest for the oatmeal cashmere?


I agree summer jackets are often an issue with jeans, but less so when the jacket fabric is thick (with an open weave). Is that sense, is mock Leno not a good fabric to pair with jeans?


Actually I have a Mechleno jacket tailor by Jerry, it is prefect match with jeans(colour and texture ), but still a little bit warm for summer, and it doesn’t look great with grey trouser. Moreover the cloth itself is not soft at all, Personal I will pick mesh collection from H&S, they added some new wool slik linen collection to mesh recently


Stanley, is the mock leno from Hardy Minnis? Do you have product number?


Hi Simon, nice article.
I have an oatmeal tweed jacket that I am not sure if I am getting the pairings right with. It feels quite casual to me , if you took the brown tweed from this article and have it the colour of the cashmere, that’s pretty much it.
It feels ok with jeans to me, but that’s about as adventurous as I’ve got with it.
My chinos are mostly not tailored, I don’t think (to be honest I find that term a little confusing, isn’t all clothing by definition tailored?) What I mean is, they seem more suitable for casual wear than with a tailored jacket. But could standard chinos work with a jacket like this?
Apart from that are there any other trouser ideas worth exploring that could make more sartorially interesting pairings with it? For either casual (say dinner at a nice restaurant with friends) or semi-formal (business events is a typical use case for me) occasions?


I think for list people “What commute you take” leads into “what office are you”.
Most people’s commute into work is so horrendous that they dress for the ease of the commute (weather , bus stop, standing in train , crushed on tube / train).

On the more specific subject of your looks I find that a sport jacket with chinos works best BUT invariably this leads to a smart upper body look and a rather faded, tired lower body look (chinos get that tired look of being creased and baggy knees very quickly).

On a more general point I think for most men just to get the colours right is a big win .
Educating men on the colour wheel of what colour to wear with what is their biggest challenge .

Lastly with the weather we are having (cold, warm, wet and windy ) if the British male was to wear a navy jacket he would need at least 3 in his wardrobe (heavy winter cloth , 3 season cloth and a summer unlined jacket).
It’s hard work looking good !


I think this is a really good point. My work wardrobe is dictated more by my 40 minute (standing) train trip with mile walk at each end, rather than anything else. Unfortunately, I also don’t have anywhere at the office to leave clothes. As a result, I’ve resorted to chinos, jacket, shirt and trainers for the commute and changing my shoes when I get to work. I often feel the issue identified in these comment of feeling like my top half is smart enough but my bottom half is like a student on work placement. It doesn’t help that in a shirt and chinos I’m one of the smartest dressed in my office, which says more about my office than me!


Robin wrote: I think for most men just to get the colours right is a big win . Educating men on the colour wheel of what colour to wear with what is their biggest challenge .”

True! Personally, I dislike the combination of tan/beige/biscuit with grey. Also in this post.

Perhaps there’s no clash going on, and I won’t pretend it cannot be done with a splash of e.g. red somewhere, but tan + grey in general looks a little dull in my eyes.

But I very much like the first picture (blue & grey) and last (brown tweed & jeans). Thanks, Simon, very informative indeed.


1, 3, 4 & 5.

And also a heavier weight linen jacket with chinos or cavalry twill trousers.

Is there a reason cavalry twill is not included in your round up.

Tim Weekes

Second this. I’d love to see a version of this article with many more odd trousers, both ones that work and don’t! Eg more relaxed chinos and why those are less good, cords, cav twills and whipcords.

Jared Phau

Loved reading this and the previous post on office wear.

I suppose the other factor (other than colour, texture) would be the style of the jacket, which you go into in your other posts.

Slight typo in para 2 of the navy jacket section. “much better tha(n) a suit without a tie”.



Brilliant article. Certainly amongst the best. Hopefully, such outfits will replace suits. Sadly, this currently doesn’t look to be the case…..


Hi Simon,

Thank you for this interesting and useful article. Could you please explain to me why your jeans would not work with your oatmeal jacket and white shirt? I am afraid I do not have a good eye for this.


Why do you hope this replaces suits?


Which raises the question what suit/s (type, brand e.g. Boglioli, Caruso etc) work best without a tie ?


Agreed! A suit without a tie just looks incomplete and sloppy quite frankly. The ideas mentioned here make men look so much better. The sport coat, shirt, no tie ensemble is much better than the suit, shirt, no tie look. Great article!

David G

I’m afraid I don’t agree that a suit without a tie lacks style or personality.

I am currently wearing a bespoke SB, single button suit in a mid/grey POW, with a light blue overcheck, from Lesser, with a pale blue highish collar stand cutaway collar shirt made for me by a shirt maker who I will not name. Paired with espresso suede loafers.

Getting me a lot of compliments today.

Tomorrow it’s charcoal grey Dugdale, made by the same tailor, with a light pink shirt and chestnut shoes with a light brogue on the toes.

These outfits sit well in my work environment. Corporate office of a high end retailer.


I think that a suit sans tie can look OK, certainly what you describe sounds like it has plenty of flair and interest.

However, more commonly out there you find a prevalence of solid charcoal and navy, white or pale blue shirt and black Oxfords. Dull as ditchwater.

Martin Brengdahl

Thanks for a interesting article! Personally I rather see a tie with suit office (I.e. for the men) since so many men lacks the interest to put more than the bare minimum of time into any ensemble and adding an additional variable will most likely in my opinion be in consequence, contradictory to the ethos of PS (as I understands it).
Kind Regards,

And a world without ties is indeed a rather dull one.


I’d prefer a tie without jacket office, rather than a jacket without tie officer, personally.

One thought of mine was around which ties would work with each of these offices since I would want to wear at tie. I think stain and printed silk ties are probably too formal. I think woven silk ties should work fine until we change from flannels to chinos. Then we’re looking at heavily textured wool ties and knitted ties, I’m thinking. And a tie is going to be hard to pull off with jeans–probably only a knitted tie at that stage?


Knitted silk better. Wool with chinos and jeans would be ok, but honestly knitted should be your first choice for any of these combinations. Cashmere would do at a pinch, but not a regular wool.

Wool is better with country clothing.


Which office am I?

Can’t see it listed here but it’s the one where the wearing of navy suits and open necked shirts is seemingly enforced by legal contract, the preferred shoe colour is ‘scuffed’ (square toe-caps optional) and the appearance of anything which vaguely hints at the possibility that the wearer may be trying to convey an impression of smartness is greeted with jocular enquiries about an impending court date / funeral / interview.


Very useful post and beautiful pictures, Simon.

Apart from woolen flannels and open-wave high twist wool trousers when the weather is cold and warm respectively, I like to have some worsted flannels and not-so-open weave (Panama?) high twist wool trousers for transitional weather.

If Tweed is too casual for one’s office (as it is in my office, save casual Friday) there you have worsted cashmere/wool (Harrison’s Millionaire bunch and similar books come to mind) and woolen cashmere/wool if you want more texture and a slightly napped surface. I say that because most Tweeds are seen in most offices as rather rustic and not appropriate. Maybe not a grey/blue Donegal but indeed a brown or green Harris. In warmer months it’s easier because cotton or linen (or mixes) are normally not that textured and have thus a much more subdued appearance if a little too boring if you like play with colors as you do in Winter. Hence I am eager to try raw silk and bamboo next year to add to my already quite completed cotton and linen summer jackets collection.


I know you refer to your navy cashmere blazer from Caliendo, when it comes to a more formal Neapolitan jacket for winter.

As my wardrobe is lacking a navy sportcoat for winter, I wonder if a pure cashmere jacket would be to delicate? As I’d wear it only with grey flannel, would a cashmere/wool make sense? Could you point me in a direction of a bunch of choice? I could see a Navy Harris Tweed (gusvs9 has a nice one from Liverano), but I guess due to it’s casualness that would only be the cloth of choice for a second sportcoat.


I’m sorry, I confused these two makers. Thank you!


I like all of these! Unfortunately, I don’t work in an office these days so most are irrelevant most days. I do travel to visit customers, however and will visit my company’s home office about once a month. When visiting customers I will usually opt for some version of the navy jacket & grey trousers look. I just got a spring weight jacket that falls somewhere (in look) between the brown tweed and the oatmeal, and am excited to wear it. My company’s home office is extremely casual (I’m talking shorts and t-shirts in summer – awful!), but I’ll usually still wear a jacket, or at least a collared shirt. Day to day I take a cue from your original post and will wear jeans or chinos with a t-shirt or oxford. My home office never gets very warm, so a cardigan is always on hand.

Thanks for another great post!


Hi Simon,
I’ve recently move jobs into a less formal environment and this along with your other “which office” article have been immensely helpful. I have started adopting style 1 and, as it’s that time of year, thought I’d ask about overcoats. Would a navy blue double breasted overcoat “work” with the navy jacket and grey flannels or should I look for something a little less structured like an Ulster?

Richard L

Simon – wonderful article, thank you. It was great to see you at the Tokyo symposium and mention ‘Which office are you’, and now we have the sequel!

This guide is really helpful when I find myself in an office that is casual internally, while external meetings can be formal (in Tokyo, often a room full of suits and ties). If a day involves the latter, I might wear levels 1-2, and throw a tie on when I head to the meeting. (Incidentally, I like your point that a pocket square might be avoided during business hours, but is nice to add when going out after work.)

If I might make a suggestion regarding summer – as we head into the hot months here, I’ve been getting a lot of wear out of a cotton-linen jacket (I found a good one at Makers Shirt Kamakura). It’s noticeably more casual than wool and, in a comparable fashion to tweed, lines up well with more casual trousers and shirts. And it feels seasonal, although of course nothing can truly resist the heat of a Tokyo summer!


I am very much 1 and 5.

Blue jacket – different shades of grey beneath. Works 4 seasons, just as suggested, swapping the weight.
Brown/beige/cream/taupe jacket – different shades of Brown/beige/cream/taupe beneath. Works 4 seasons and love tonal.


My (high-tech) company has gone from requiring a tie for all customer meetings to needing no tie and to an inexplicable encouragement for jeans with sports jacket/shirt. I find it almost comical that the older gents cleave tightly to this “cool” radical new uniform. I think jeans have their place but it’s not below a sports jacket, especially on 40- or 50-year old men like me. I’ve nothing against denim per se, especially in lighter colours, but wearing the full “jeans” look of indigo denim featuring gold thread and rivets simply looks tragic on older men in an office setting.
Maybe it’s just me.


Great post, Simon! I’m sure it’ll be added to many people’s bookmarks, as I just did myself.

I understand that this was just an abbreviated illustration of the formality spectrum, but where would you place jackets made of corduroy or patterned jackets of various materials? I think a glen check could suit flannels and chinos, but could it even extend to denim with the right (lack of) structure? On the other hand, I can see corduroy working well with denim, but how far in the direction of flannels would you pair it with?


I work at an academic library, and I wear combinations similar to all of these. I also wear neckties with regularity. However, I am the only one dressing like this most of the time. My male coworkers wear chinos, polo shirts, and casual shoes or sneakers, so I always look like I’m a bit overdressed for my workplace. I really enjoy classic menswear and don’t plan on changing the way I dress to fit the super casual atmosphere. And, thankfully, I’ve never been pressured to conform.


Simon, I may have missed something but how is that navy jacket different from a suit jacket? Is it mainly the fabric?


Could you say a little more on this, Simon, and maybe expand on how far you can take those steps away from a navy suit jacket before it become too informal? I’ve been thinking a lot lately of how the navy and grey is particularly well suited to any engagement I might have for work these days given that 1. Suits for work seem to have taken their last breath during Covid and 2. I find corporate attire (even in finance) tends to be more casual than in the US compared to the UK. What I’m really nervous of though is having a jacket that looks like a stiff, orphaned navy suit jacket paired with trousers that — while appropriately formal (wool) — also appear to be the bottom half of a stiff grey suit. Everything I see that is a navy sport coat seems to have too much texture to pass muster as formal enough (hopsack for example) or looks like aforementioned orphaned jacket. Perhaps it comes down to seeing the fabrics in person vs online.


Hi Simon-

I’m in an office that would probably be one or two down from the most formal option you present below and I am working on expanding my odd jacket wardrobe at the moment. I just picked an 12 oz oatmeal/grey Wbill shetland tweed for a winter odd jacket with Steven Hitchcock. Its tweed but the color is very subdued and comes off as a bit sharper than a green or brown country tweed. It would be worn with charcoal flannels and brown cavalry twills and open necked denim or oxford shirts.

I was thinking of a single button with straight flapped pockets and a ticket pocket, something of a play on a hacking jacket. Seeing so many of your odd jackets styled with two buttons and patch pockets, I’m considering whether I should adjust the style.

Thoughts on whether my proposed hacking jacket style would work in the context described above? I appreciate the input. Thanks.


A hacking jacket has slanted pockets and a centre vent, for very practical reasons, given its intended use.

If it doesn’t have these details, it is not as hacking jacket, and therefore should not be referred to as one.

Simple but important stuff.


Hi Simon,
Excellent post!


Is there anything specifically different with the oatmeal jacket(caliendo) to the tweed caliendo/ettore on the shoulders? It seems more elongated for the oatmeal giving a softer look – is this to do with the fabric or is it a different construction in the shouldeR?

R Abbott

What type of tie would you wear with outfits 2 and 3?


Do you think a dark brown grenadine or knit tie would work with the oatmeal jacket and flannel outfit?


Ciao Simon. I think it would be very interesting to explore double breasted jacket in the same subject. I think it will add much more variation for office ))


I was surprised not to see a Double Breasted included in the parade.
No self respecting flaneur should be without one.
I have a nice linen/silk blue stub melange (Zegna cloth) that is now about ten years old and is perfect for summer.
DB’s also serve to stop the whole thing looking like a uniform .


I don’t think a DB works well in anything less than a relatively formal environment.


Anonymous, you simply haven’t got the right DB.
We aren’t talking the Prince Of Wales here.
Cashmere navy blue with brown horn buttons and patch side pockets works perfectly with jeans or grey flannels in the most casual of environments.
Looks great with roll neck sweater, white shirt or vintage denim shirt (grey flannels only).
Dark brown suede shoes or Chelsea boots are a must with all combos.
Only the more advanced flaneurs need apply.


Thanks Jason. Sounds terrible to me!

Simon Miles

I think many men, myself included, have a hard time navigating that difficult space between casual and formal. And yet this is the space modern man occupies much of the time, so it’s something we need to understand. This may just be the most useful and accessible guide on the subject I’ve read. Thank you so much for sharing. If I have a question still unanswered, it would be about pocket squares. What effect on formality, given that few men wear them? What advice for those of us who feel self-conscious wearing them, particularly in a more casual environment? And if no pocket square, does this affect choice of shirt or jacket?

Simon Miles

Thanks Simon, that’s very helpful and I appreciate you taking the time to reply.


Don’t they look affected.
They are a distraction and should only be sported with evening attire.
Unless of course you want to take the eye away from a poorly cut suit or jacket. None of the great flaneurs wear them


@Jason. I’m annoyed with that flaneur-BS. Who are you to dictate some kind of rules and to define what looks good and what not?


JDV don’t be annoyed.
I was only responding to Simon Miles’ question regarding pocket handkerchiefs .
I would never dictate rules but would merely offer my opinion – as one flaneur to another !


How can you wear a pocket square with evening attire? Nonsense.



May I suggest that anything other than ivory silk as a pocket square with black tie is a nonsense. Neither vague, nor dismissive. Simply correct.


Purely on what is customary and traditional. Black tie is is called for a reason. An ivory pocket square would be the only acceptable adornment.

Once you move into green or burgundy or paisley ties, with matching cummerbund, you are moving into fashion, away from tradition.

And so it would be with anything other than an ivory pocket square.


Simon I have long considered that gorgeous oatmeal LP cashmere fabric but am still wondering whether it is much warmer than a 340g wool. What would be the max temp at which you d wear it with a shirt?


“What I hope to be the future of professional office wear” – I think that’s spot on: guys would look so much better. As for my own office, I see the CEO in 5 or 6 perhaps once a month. Otherwise I don’t think I’ve ever seen anyone wear a jacket.

In my workplace these would stand out because it’s a step up in formality but even where this is equivalent formality (as you say, grey trousers and navy jacket should be the same or smarter than a suit and no tie) there’s also the issue of normality: if everyone else is in a suit and no tie and you’re the only one in separates, you’re still going to stand out.

My guess is that most workplaces (in the UK, at least) these days are either suits offices (most of which are now ditching the tie) or anything goes. And if there’s a “middle” category at the moment – between suits and anything goes – it’s probably chinos (or smarter trousers) and shirt but no jacket. Maybe with a fleece country gilet (you know the type with the brown trim) and brightly coloured socks if you’re that kind of chartered surveyor.

I wonder if there are workplaces where the sort of outfits shown here are common rather than the exception? I fear in other contexts, even if you get the formality right, you’ll still stand out on the normality front.


First time asking you a question and a bit anxious given your vast knowledge.

Do you think light/mid brown trousers and a pink shirt would make a good pairing? If so, burgundy shoes or dark blue?

Thanks in advance

R Abbott

Actually, my experience has been that sports jacket and trousers are the norm at offices where suit and tie used to be but no longer are required. For instance, at my office, people still wear suits for client meetings, court room appearances, etc. but otherwise the norm is to wear jacket and trousers, with or without a tie. (Trousers are still the norm—chinos are not prohibited but are pretty unusual, except on Fridays. Jeans are only allowed on Fridays, and even then, people tend to pear them with a collared shirt or polo and a sports jacket.)

Tom S

Love this Simon. Living in London, what fabric / weight might you suggest if you had just one blue jacket?


Great article Simon and very relevant for my office. My question is actually about your jeans, why are they now tight? I understood that quality denim like cone mills should stop shrinking after 2-3 washes. I’ve recently bought a pair, hence the question.


Fun and interesting article.

I had question regarding camel hair jackets. In terms of formality, would a camel hair jacket be on par with 1 or more in line with 2 (assuming trousers remain similar)? Do you have any advice on how to style a camel hair jacket in terms of structure, pockets, and buttons? And how seasonal do you view camel hair jackets?


Camel hair is not a jacketing. It is a coating.

Simon why don’t you help point this type of thing out?


Simon, are you confusing camel hair and camel colour?

The former is a coating, the latter can be anything you want.


Dear Simon,

Thank you for an informative and practical article. A question. Would knitwear under a jacket be acceptable? I’m thinking of a lightweight merino half zip or turtleneck, dispensing with the shirt altogether?

Priscilla Leung

Would these outfits qualify as smart casual Simon? What one overcoat would you wear with all of these?

Would the three jackets in their specific cloths be your recommendation for someone starting out their sports jacket closet? And the suede cap toe? It seems to be a versatile shoe.


Wouldn’t a navy overcoat work with all three of these outfits? Why did you think of herringbone first – just curious color-wise.

And if you had to pair a tie with these outfits would you?

Could you think of a shoe besides this suede adelaide that would also suit all of these outfits?


Would you go for mid grey or a darker/charcoal grey herringbone?

I’m concerned mid grey herringbone may err on dandy/flashy?

Gracias Simon



Why wouldn’t you recommend a brown tengri overcoat over a herringbone, as a second overcoat? The tengri looks more muted and versatile in my opinion.

Peter K

I think some men adopt the suit sans tie look because they in an office where meetings still require a suit and tie. They can be “casual” most of the time and just add a tie for meetings.

It is versatile and doesn’t require a lot of thought, even though it doesn’t look very good on most men.

A reflection of practicality more than a style choice.

Tom S

Thanks Simon. And would you single out a particular weave / kind of wool for that 11/13oz blue jacket?


…on pocket squares and evening dress: Simon is absolutely correct. The tradition (for evening dress) stems from the first half of the twentieth century wherein a pocket square was worn in the same way a tie was – it was a fundamental part of the costume.
Simon Cranston has written the following well researched monograph on the subjects:
It is also worth noting that many menswear advice guides formulate a pocket square as de rigueur for evening dress.


Hi Simon

Have been reading this with interest and, whilst I haven’t posted on PS for a while, feel moved to contribute.

I agree wholly with your position; black tie means exactly that, so no horrible fashion twists. And white, ivory or cream silk or linen in the top pocket are fine, perhaps with a pop of colour in the body for interest.

But I do worry a bit when internet sites are used as reference to support an argument, rather than experience.


Hi Simon,

Very informative as always! In view of this gradient of formality, what is your opinion on the most versatile type (and hence the recommended order of purchase) of sports-jackets? Perhaps we could get a capsule collection article on this subject some time!



Hello Simon,

great article. One question that bugs me for some time: Where would a navy tweed jacket be on that scale?
With its more formal colour but less formal fabric/structure.
Of course this strongly depends on the specific tweed.
But it would be great to hear your opinion about navy tweed jackets.




I suppose this kind of analysis is very ad hoc? For example, I have a cashmere navy tweed that I wear very much like No. 1, and probably a bit more formally with poplin non-BD shirts and slightly dressier shoes (for example, cap-toed double-monks or laced derby ankle boots). This is a bit like the not-quite-navy blue tweed Disguisery made for you that you wore in an article dated 2017 pretty formally (tie, poplin dress shirt, lace-up dress shoes). Similarly, I’ve considered getting a cashmere/silk donegal in navy to wear the same way, on the theory that the color and lux fabric will give me some flexibility ascending, as well as descending, the formality scale.


You speak of a blazer and grey flannel trousers as an ‘American Classic’. The New York Style Magazine reports that in 1924, (whilst holidaying in NY), the then Prince of Wales (later Duke of Windsor) wore gray (sic) flannel trousers as part of an outfit, which, as a style, was then copied.
Bruce Boyer expands further on the theme and describes the popularization of clothing items, such as the blazer, during this time due to British influence.


I was in Jermyn St last week and observed a beautifully tailored example of the blazer and flannel combination on a businessman, so examples remain here. Accepting its status in the US why do you think it has become such a popular choice – does the UK or Europe (stroller?) have an equivalency?


Hi, Simon.
Superb article as always!
I have a question, which hopsack would you recommend for my first navy 3season sports jacket. Considering a hopsack from Fox, but would love to hear your recommendations/experience.
Kind regards


You have two of these brown suede oxfords, another the Canterbury by EG. Any particular reason why?


That second to last picture with the tweed jacket and jeans makes me long for autumn. Such a great fabric.


Hi Simon,
Excellent article. I understand your post on a capsule of sports jackets is sill some time away so I ask for a preview. Looking for an appropriate and versatile collection for someone who works in a formal environment where sports jackets/odd trousers can be worn 1-2 times a week. I live in NYC so need to account for summer and winter and was considering to work my way towards: (1) navy hopsack 8.5oz, (2) taupe or oatmeal summer wool fabric 9oz, (3) navy hopsack 12oz for 3 seasons, (4) navy cashmere (5) oatmeal cashmere, (6) dark grey herringbone tweed.
Any thoughts? Thank you in advance.

Ian A

Hi Simon which Bespoke tailored jacket do you find the most comfortable out of the ones you’ve tried purely from that point?

I’ve tried one from Solito and one from Graham Browne and personally I find the GB one more comfortable if like me you enjoy wearing a tie with your jacket.


Thanks Simon, a neat overview for me and also a great entry point to your site as a recent joiner. AM interested in your views on how to carry off dark blue, indigo jeans. Somehow I find more worn, lighter jeans easier to get away with – just about any sort of jacket if its got a texture. Dark blue jeans though do not seem to work with blue blazer/sports jacket and neither with lighter jacket (although perhaps with light grey). Any guides or rules of thumb which you might have to share?

Chris Tinkler

Thanks for the very interesting article on good quality, informal clothes, Simon.
I’ve always been partial to separates (i.e., not a suit but a coat and trousers) in the office, but have also liked wearing a suit, particularly when I worked in London but, as you often don’t wear a jacket in the office itself, it’s rendered meaningless.
Now that I live way out in the sticks (North Yorks Moors) in an environment where formal clothes aren’t a mainstream look, I struggle to find a reason for wearing a suit rather than a more casual outfit and the tailor I go to (Des Merrion) even “nudged” me from buying suits which would be infrequently used to getting items that would be more regularly used: a good example of a tailor listening to a client and putting his best interests first.
More of the same would be appreciated.
Best regards

Chris Tinkler

Well Simon, tweed coats and accompanying cavalry twill or flannel trousers are a pleasure to wear and mix well with whatever other people are wearing (it’s alright to have nicer clothes around here as long as they’re not considered “flash”).
The main problem during daytime is footwear as we are at the base of some rather steep hills and rain brings a lot of grit down onto the paths, making it very abrasive for normal “city” leather soles. This results in needing rubber soles as the usual local footware (mainly chukka boots) moving the clothes down into the casual area.
As we go out quite a lot on the evenings, there’s not so big an issue on footware but still the emphasis is on casual rather than formal.
Best regards


I’m about to commission my first sports jacket and just wanted to check with you about pocket style. I read some general statement somewhere that if your side pockets are patch pockets then the chest pocket should also be a patch pocket. Do you agree with this statement? (I think I’ve seen a few pictures of you in jackets with a jetted chest pocket and patch side pockets, which is what I actually want.) Does this affect formality in any way? Or is it just up to looks and which design I like the most?

Tom Dell'Aringa

I’m new to your site and just loved this article. I only got interested in men’s fashion at 50, if you can believe it. Now 53, it has been a long learning curve after the initial burst of information. The steps here are so instructive. I would love to see more of these articles based on other scenarios. Would also be great to see you do this sort of thing on your video channel. Keep up the great work. Signed up for your email list. I don’t have the means to go after the clothing advertised here, but it sure is fun to look at 🙂


Any advice regarding hacking pockets on an odd jacket, versus straight flaps or jetted pockets? I’m thinking of odd jackets suitable for a business-casual office, and I’m concerned that jetted might be too formal for an odd jacket, but would like something with a bit more personality than a straight flapped pocket (and I’m not interested in patch pockets; I have plenty of those). Thanks in advance!


How much leeway do you think you’d have with shirts to go with something like the brown coat? You’ve gone with a pretty informal oxford-cloth here; what about a relatively informal poplin or twill in blue, or something you might normally wear with a suit (a shinier less textured cloth) but with stripes to take the starch out of it? If the brown coat were a touch more formal, say a smoother cashmere Donegal, wouldn’t that permit more options? The interplay of formality, texture, material, color, and cut is really fascinating.


What colour would you choose instead of navy or oatmeal for office wear (formality of point 1 or 2)? Perphaps a light or dark grey? What trouser colours would you wear with it?

Is oatmeal an issue with a pale skin tone or is it “cold” enough?

Is oatmeal smart enough for fridays at a very formal office where most people just wear suits without ties on fridays? In such a office blues and greys dominate so oatmeal may look a little bit out of place or what do you think Simon?


What about a navy DB jacket (neapolitan) as a second jacket for fridays?

Would you were a DB jacket at firms like consulting or in finance?


Does the formality of the navy blazer with grey trousers outfit change if one replaces the mid-grey with light grey trousers?


Does it make a difference wether the trousers are light grey or pale grey flannel?

On the pictures of your “INTRODUCING: THE INDULGENT SHAWL-COLLAR CARDIGAN” post you wore light grey flannel trousers which for me look much better with navy than the pale grey flannel trousers you wore on the pictures of the old “Which office are you?” post.


Simon, I wear softly structured suits in navy and dark grey most days. The trousers always have a cuff, what is your take on wearing some well maintained black Chelsea boots? I only wear black oxfords presently but have ordered some sleek Chelsea’s and am wondering if the cuffed trouser is compatible with the more casual shoe. Thank you.


You have a hopsack in 8oz and a mesh in 9oz. Is this the range one should look at when choosing a hopsack fabric? At what weight is hopsack considered heavy?


Hi Simon,

During Lockdown I have been spending a lot of time on PS. Thank you for all the effort you put into it – it has been a great distraction.

Of all the articles, this is the one I keep returning to. More guides along these lines – “how to”s, guides and checklists – would be brilliant.

Many thanks




I suppose it could be an articulation of some “rules” which may come naturally to much of your readership, but could really help avoid some expensive mistakes.

It could be:

(i) Some basic dressing rules – never navy trousers as separates, shoes being darker than trousers – all in one place. Maybe also showing how it can go very wrong.

(ii) Something around how to get most value from an item – I am a huge fan of £/wear (hence I have always bought Northampton shoes since starting my working life).

(iii) Fit and style based on body shape, colouring etc. I have a paunch and it always shows.

(iv) Maybe a “swap one item” piece as above but which could take you from Spring to Autumn.

Many thanks and best wishes


Ayush Saraf

Hi Simon! Another lovely and a very useful post.
I just wanted to know that whether ‘can I wear a navy hopsack sports jacket with ‘khakhi chinos’ purchased from gap’? This is because I want to purchase a blazer which can seamlessly transition from office to a smart casual function and chinos are the only thing which can work in smart casual functions.
I have asked this question because I have read almost all of your posts and you have always seemed a little concerned with the brand of chinos which a person would be wearing. In India we do not have much brands to choose from and the brands which have been suggested by you would exceed my budget.
It would be highly appreciated if you could guide me.


Thank you so much for the advice!
So for a smart casual function can I wear medium grey wool trouser instead of chinos?
And how would have you dressed up for a smart casual function if you did not have a good pair of chinos available and grey flannels would have been too hot considering the climate?
‘Asking this question because I have read certain articles of certain people wherein wool trousers are considered to be an office garment and not acceptable in a smart casual function’!


Thank you so much Simon!
Would be waiting for the day to meet you in person and take some style advice.
Do you take personal appointments and if yes then when are you scheduling a trip to India?

Would love to read an article from you on how can men add colours into their wardrobe!


This Harris tweed jacket is so versatile. Do you think a colder brown version of the same would work just as well? Ie is there a version of this that could still be compatible with the cold colour capsule? Or is it better to build a bigger collection and go for a rough tweed in a warm fuzzy brown like this; and separately go for a colder colour in wool to be more formal?

Matt L

Hi Simon.
Looking back at this old article, I notice you mentioned one outfit as being suitable for a tech executive, but not for a lawyer. I was wondering if you could talk more about judging these things? What should people expect from a law firm versus banks, tech, government etc.
Obviously I’m referring to the senior roles where sartorial clothing is expected. I know first hand how many t-shirts and jeans there are in the tech world.


The funny thing I have realized after some time is that I could wear any of the 1-5 above pretty interchangeably at work, and no one would really notice. I’ve seen people do worse than 6 (i.e. jeans and sweater, often with, sometimes without dress shirt), and in fact nowadays a lot of people don’t bother with a jacket at all; still, I personally wouldn’t go as far as faded indigo jeans myself, though I have worn ecru jeans + sport coat in some occasions.


1. Navy jacket and grey trousers : Hello Simon. In this same combination, if I replace your Shoes: Brown-suede oxfords with mine https://www.yuketen.com/shop-last-pair/santiago-fo-snuff. I would personally want to style it this way for myself. Let me know your thoughts on this one?


Hi Simon, I was wondering how many buttons you would usually put on the sports jacket?
Many thanks,


Hi Simon, thanks, but I couldn’t find how many buttons were ideal for the sports jacket’s cuff. Could you share a link for me, if you don’t mind?


Interesting, thank you.


Hi Simon, if it were you, would you wear a combination of bespoke dark brown wool (spring/summer) sports jacket, dark-mid chambray shirt, stone cotton single-pleated trousers and black suede tassel loafer?
Many thanks,


Great, thanks.


Hi Simon,

Would you wear a dark brown tweed sports jacket, dark brown vest cardigan, mid-grey flannel trousers and black cap-toe oxford?

Many thanks,


I see. Could a pair of dark brown calf wingtip brogue oxford work, then?


Hi Simon – I was wondering, what kind of tie (in terms of color and style) might you wear with the fourth outfit (brown tweed and flannels)? Are there one or two options you could suggest?

I find I struggle a bit with this. I’ll wear an outfit like yours, in the same way you’ve pictured it — with an open button down and no tie. If I wear a tie it’s generally with a suit (in a standard, “business” worsted). I’m less sure about a tie pairing if it’s a setting where I’d want to combine a tie with the more casual tailoring.


Thanks, Simon, as always. I didn’t want to bias the jury, but I suspected that your advice might include a knitted tie.

One more point of minutiae, if it’s not too much: Would you hesitate at all in pairing a grey wool tie with grey flannels?


Hi Simon,
Fantastic article and one I’ve regularly come back to over the years. I was wondering what you’d suggest as an alternative to the white twill and oxford shirts for the warmer days of summer. I work in quite formal office environment and I feel linen isn’t quite smart enough, Fridays excepted. For instance, how do you feel about button-down poplin shirts, like those offered by Anglo-Italian and Drake’s?


Thanks for the suggestion Simon! In a way, a cotton/linen shirt with a sports jacket is quite a neat fit in terms of formality – sitting in between the poplin shirts I wear with suits and the linen shirts I wear with more casual outfits when it’s hot


Dear Mr Crompton

I was wondering whether you can give me some advice as to how to develop and understand my own style. I do not want to appear too conservative, so a (dark) charcoal or navy worsted suit is maybe not my first choice. On the other hand I am not the guy to wear country colours, no brown/green cavalry twill suit and no brownish/yellowish shirts. Still I want to be smartly and sharply dressed, I want to wear standard white, pink, and blue shirts (poplin and oxford, occasionally with french cuffs), I want to wear silk ties in burgundy / navy / green / purple and I want to be able to use both black or brown shoes. Sometimes I think I want to look like a well dressed journalist or left wing politician (not like a banker or city lawyer even though I *am* a banker) and I also like the style of how Ralph Lauren present their clothes and I want to be able to look appropriate in both work (slightly conservative office) and play (I do not mind being overdressed and I am not rich by any minds and I don’t hang out with rich people), changing the look of the whole thing by going from silk to wool tie or from white to green checked shirt and so on. Do these thoughts make any sense to you and are you getting the point what my desired look is?

So far that led me to buying suits in mid brown high twist, mid grey melange 280gr, mid grey fresco DB, light grey windowpane 260gr. Thinking about jackets in navy / dark green to add to my charcoal herringbone jacket (Fox Sommerset). Also thinking about mid grey flannels and tan cavalry twill to add to my light grey flannel (Fox Classic Flannel) trousers. Also thinking about a mid to dark grey suit, this time in a winter weight flannel. Is there any other suit colour for me? I fear another brown suit might be too casual and I might not be able to dress it up that much so maybe I am stuck with mid grey? Also in my mind is navy flannel but I’d rather have a navy jacket with a lighter bottom because I don’t have dark brown shoes to wear with a navy suit, just mid brown shoes to wear with a mid grey trouser. Considering I also have brown moleskins and burgundy corduroys for the colder months and also dark blue denims, as well as two summer jackets in dark blue and mid brown and some summer trousers (creme linen, olive cotton, beige cotton), what do you make of my thoughts on planned future buys and how would you recommend I develop my style?

Thanks a lot!


Very helpful, Simon, thank you so much. I have read some articles and comments and I am still finding out how far certain elements can match. Will ask in the referenced articles!


Hi Simon,

Just wondering where those light beige/taupe colour socks are from?

Have been trying to find ones in a similar shade for ages to no success.



Hi Simon, apologies if this has been discussed elsewhere but do you have recommendations for brown jacketing for an office? I feel the harris tweed would be a bit to hairy for me. I was looking at Donegals with low contrast flakes but would appreciate if you have any other suggestions


Hi Simon, is the first shirt (the twill one) a button-down (i am unsure looking at the picture, also there is no info in the comment section about it)?
Would a dark brown split toe derby also work with all the outfits?
Kind regards as always