Trousers and what they go with: A sliding scale of formality

Monday, September 26th 2022
||- Begin Content -||

When we published our second capsule guide to trousers recently, there was a discussion in the comments as to their smartness - and a request for an article setting it out. 

Now, trousers vary in more than just their material, so this will always be a simplification. But trousers are relatively simple compared to shoes or jackets, so I think there is something sensible to say. 

Just keep in mind that these brief guides are a starting point - a way to understand the factors (more texture is more casual, muted colours are smarter) rather than a set of rules. 

So with that always in mind, here is a sliding scale of formality of trousers, with notes on what else - as a result - they might go with. Apologies to those that will find it basic, but I know now that some readers will find it useful.

We’ll go from the smartest to the most casual.

Wool gabardine, mohair, superfine worsteds

A normal business suit is made from worsted wool - fine wool that has been processed to be smoother and sleeker. That’s why it’s different from a hairy tweed jacket. 

Some worsteds are especially fine, or particularly processed, to be sleeker still. These, such as wool gabardine, are usually seen as smarter than regular worsted; and while mohair has a different, crisper handle, it has a similar sharpness. 

Shoes: These worsteds are most suited to shoes such as oxfords, that are also sleeker given they don’t have the extra leather layers of a derby. Usually calf rather than suede; usually darker colours. 

Upper half: Most usually worn with a smart jacket such as a blazer, or a particularly fine knit. 

Regular worsteds

As above, but more like a standard business suit. And usually not the preferred choice for trousers on their own anyway. A navy pair worn with a white shirt won’t look wrong, but it will probably look like there’s a matching jacket somewhere.

If you want separate trousers for a work environment, best to go for something like flannel, or even cavalry twill, that doesn’t look like it’s part of a suit. 

Shoes and upper half: If you do wear suit trousers in this manner, then same as above

Textured twills and high twists

The group I've called 'textured twills' includes cavalry twill, covert and whipcord. They all have much the same sharpness as the worsteds above, but aren't as fine and usually have a little more texture. They’re also usually in less formal colours, such as greens, beiges and browns. But they don’t have to be.

I'd put high-twist wool in the same bucket. It's a summer material, but also has the sharpness of a normal suiting with a little more texture by natural of its twisted yarn and open weave.

There is, by the way, more comprehensive information on all these fabrics in the PS Guide to Cloth.

Shoes: These sub-sections get easier and more predictable as we descend the smartness scale. A textured twill such as whipcord is more likely to suit a brogue, a derby or a boot, and a brown shoe rather than black. But as always there is more than one variable, so a charcoal whipcord could be great with a black boot, for example, because it’s a smarter colour.

Upper half: We’re getting into the realm of more textured jackets, such as fluffier cashmere and tweed. Knits can be fine, but smarter shetlands, for example, also work. 


The old favourite. A woollen rather than a worsted, so without that fineness, and with a napped finish that gives it a little fuzziness. 

Flannel is great at bridging casual and formal; perhaps the best. And annoyingly there’s little in the summer that does it as well.

Shoes: A classic grey flannel works with black leather shoes and a white shirt, but also with a brown suede boot and a crewneck.

Upper half: As above, good with a navy blazer or a tweed jacket, a fine V-neck or a shetland. If you imagine all these categories as overlapping sections of a scale, rather than single points, then flannel is a wider section than most. 


Linen is tricky because its formality varies quite a lot depending on its weight. A heavier, starchier Irish linen is arguably very elegant and could sit above flannel on this scale. But a lighter, Italian one could be made with a drawstring and be fine on the beach. 

I think it’s important to remember this versatility and see it as a strength rather than a complication. You could wear nothing else all summer and cross several types of smartness. 

Shoes: Rarely an oxford, but most other things, particularly loafers given it’s a summer material. And at the casual end everything like espadrilles and sandals. 

Upper half: As above. Tailored jackets to T-shirts. 

Tailored cottons, moleskin and cords

This section could be divided up further: many tailored cottons look smarter than any corduroy. The latter is more casual by virtue of its texture, as is moleskin. 

But the important point here is that cotton is nearly always less smart than wool; and that this is a separate category to chinos or khakis, which come next. 

Shoes: Not oxfords, but derbys and loafers, no blacks, and suede as well as leather.

Upper half: Not a T-shirt, and not a smart blazer or fine knit, but everything else in between. 


A chino will usually be made from a less fine cotton than the types above; it will only have a simple waistband; it’s more likely to have raised seams and other details.

You know what a chino is. But these are the reasons it is in a different category to the cottons above, and they are why it looks different too - eg it doesn’t really drape, it just sits there, more like a denim. 

Shoes: Slightly more casual than the tailored cottons, and therefore suited to slightly more casual shoes. For example, perhaps not a fairly smart brown-calf derby. But then at the bottom end, anything you want, including trainers/sneakers. 

Upper half: There is an American style that involves wearing jackets with chinos and it can look good, but it’s quite specific (roomier jacket etc). Most of the time chinos aren’t the best with a jacket, and should be kept to more casual partners, such as a suede blouson or overshirt. 


You don’t need to be told that jeans are at the bottom of this list, or probably that a dark, indigo, unfaded jean is smarter than a light, blue, faded one full of holes. But they’re here for the sake of completeness. 

It might also be worth saying that white jeans are in some ways the smartest of all denim. And as a long as it isn’t dark and raining, they’re quite versatile. 

Shoes: Same as chinos although, oddly, I think some leather shoes work better with jeans than chinos. Eg a tan derby.

Upper half: Same as chinos although, equally, I find tweed jackets better with jeans most of the time. 


The point of this article was to answer reader questions, so please tell me if I have. And if I haven’t, tell me how - I’ll add answers in the comments, or supplement the above. The whole of PS is basically an extended Q&A anyway.


Notify of

Inline Feedbacks
View all comments
Lindsay McKee

Simon, you could not have timed it better!
A superb article on trouser formality and a great help to me and others.
Where would you rank Venetian and Bedford Cord?
I encourage you, if you haven’t already, to have a look at the Dugdale’s ‘Invincible’ Bunch and Smith Woolens ‘Whipcords & Cavalery Twills’ Bunch which have some beautiful cloths.
A grey whipcord from the latter bunch is part of my current commission with Steed Bespoke.
Great Post!!!


Two questions .

1 On the subject of linen trousers why are they almost always straight or wide legged?

I’ve desperately looked for linen trousers with a taper and decent pockets (frog pockets) .
Can anyone recommend linen trousers with both .

2 Might I add that what also needs mentioning is a utilitarian trouser …. Something that can handle a commute, weather , good pockets that can’t be pick-pocketed .

(What is it with me and pockets !?)

Great article .
Reminds me of that little book I came across many , many years ago with your name on it explaining very basic principles of menswear.


Utilitarian trouser  ? … I suppose I mean something functional , smart , durable , practical and hard wearing .
I know sometimes you see trousers with draw-string elasticated waist band , zip pockets and a fabric blend that allows it to be worn say cycling on a ‘Boris bike’ but then transfers well to the office and at the end of the day to the pub.
One that isn’t a jean and is more resilient than a chino .
Maybe others can recommend something.

P.S. Yes ! The Snob book .


Hello Robin,
just a few thoughts on the “utilitarian” trouser. As a commuter cyclist I’ve been experimenting a bit and eventually found that in cold weather a pair of cavalry twill trousers fits the bill quite nicely. This fabric is sturdy and windproof but still can drape nicely and offer a fairly smart (well, smart-casual) look. A wider cut might be a reasonable choice as a close-fitting leg will be much more prone to wrinkling etc. with all the stress the fabric gets while you ride.
In warm weather I’d go with some linen or cotton-linen blend. Of course they will crease but it it’s a type of fabric in which a few wrinkles don’t necessarily ruin the look.
But then, as Simon said, utilitarian qualities rarely go hand in hand with a smart look. The question here is one of finding the right balance between these 2 aspects. Is a sleek look your priority? Is it comfort and ease of movement? Is it weather protection? etc…


Interested to know where you would place various blended trousers such as this wool/cotton mix by VBC from Cavour:
to me, it feels like it belongs with high twists but is slightly less formal.
Similar case with cotton/linen trousers. Would the cotton in the blend make it less prone to creases and therefore, more formal than a pure linen trouser? or would it be more affected by other factors such as the texture and weight of the fabric


“And annoyingly there’s little in the summer that does it as well.”
That is so true! I tried heavy high twists to solve this dilemma, but it sitll isn’t the same.
By the way, what tweed jacket are your wearing with those Full Count blue jeans? That combination looks particularily tasty.

Aaron l

Come to New Zealand, we never have true summer. Tweed all year!


Hi Simon,
No big surprises here – there really shouldn’t be any of course. Always nice to see everything on a scale for reference however. One point I’d like to contest you a little bit on is corduroy. I find that a dark corduroy looks quite smart in the evening, its velvety characteristics make it rather chique in my opinion. Naturally, this doesn’t really go for a brown or khaki cord. In this line of reasoning, you did not mention velvet (it’s not a typical trouser material of course), would you put that with the rest of the cottons?


I think Zegna’s CashCo cloth is well worth a shout out here. I’ve had a few pieces made with it – both jackets and trousers. It combines the softened of cashmere with the durability of cotton and comes in a range of beautiful colours that make it suitable for day and night.


Due to the cut perhaps, or the way they fit, I find that worsteds trousers are more versatile than many would care to admit. This is especially true in function, if not as much form. They hang naturally on the body and can be fitted more loosely than many other type of trousers, yet still look sleek, as perfectly demonstrated in third picture in the dark pinstripe. Due to this characteristic, they also feel comfortable during summer and spring, when other types of wool can feel much warmer, if not out of place altogether. Needless to say that I am a huge fan and to my mind, nothing else in wool offers the versatility and elegance that comes with this type of garment. I could go on about the other uses, e.g. easy to clean, hardiness in general, etc.

Aaron l

Please do! I never hear much praise of worsted wool.


Great article.
Personally I think that finish should vary with levels of formality.
The most formal featuring side fasteners – the rest featuring belt loops ?
Now that ties are little worn, belts have assumed a new importance. They offer a focal point. A point of separation and a vehicle for self expression.
For me, cuffs or no cuffs / pleats or flat front – is a matter of taste. I have both.


I know you mentioned it in a previous article about left-hand vs right-hand twill and which one is smarter, but I cannot find it now. Might it be an idea to include that for completeness sake in the tailored cotton section?
As a side question, are there any particular or prominent weave/fabric names used for tailored cotton? I’m aware of cotton gabardine and obviously seersucker, but I’ve seen drill mentioned before (and for shirts too).


Fantastic article! Just the refresher course on the differences between worsted wool and the other woolens was very helpful.


I have a pair of 16 oz, 8 wale olive cords(cordings) which are so useful -especially during the current changeable weather. As you say, they go with just about everything(bar tailoring) and most footwear. Easy to smarten up or down.


Where would you put tweed trousers here? And I assume brushed cottons fall under the category of Textured Twills?


Great article, Simon.
I have one question: In your opinion, do pleats and/or side adjusters increase the formality of trousers.

Ras Minkah

I saw you on Savile Row this afternoon what an incredibly handsome and very stylish man you are Simon. Had I been smarter dressed I’d have introduced myself and complimented you on what fantastic work you do. Keep it up.


Hi Simon
For footwear under cords you say “no blacks” – I’m a little confused – could you expand more on this? Is even a black loafer (in suede, cordovan etc) definitely too formal for cord? I had imagined it might look quite modern with your dark brown cold cords. Why is it that black shoes work for some brown flannels but not for brown cords? A formality thing?


Thanks Simon – on a similar last, like the Belgravia, how would you rate the relative formality of a black suede versus a black cordovan versus black calf? Is cordovan the most relaxed?

george rau

Is there a reason you cuff jeans and chinos ?


So… if one happens onto a pair of nice jeans with an inseam within shrinking distance from length of leg then it’s a statement to buy those instead of looking for a pair that doesn’t fit as well? Isn’t that going a bit far? They’re just jeans, right? First they’re too big, then they’re just right, then they’re faded, then there are holes, and some of the nicest ones get repairs, too?
With my inseam of ~30” jeans that fit are never really one of my problems, but when the inseam winds up just right it is certainly no statement, it’s more like a cosmically fortuitous miracle of alignment of denim and spin cycle. Then you wear them happily and try to remember to not spin them anymore, and eventually fail, at which point your new jeans will have cuffs again, or stacks, or both?


Is your Fox Flannel trousers double pleated?

Simon G

Hi Simon,
Great article. For my two cents, revisiting the basics helped me to really re-engage and think about some of my wardrobe in a way I hadn’t before.


Hi Simon, I hope you don’t mind me asking a quick question. I’m having a jacket made by an Italian tailor, with all fittings taking place in London. I paid half the cost up front but I’ve been told that I have to pay the other half at the first fitting. Is this normal? When I’ve had bespoke made by a London tailor it’s been half up front and half when the item is completely finished, which feels more equitable. Many thanks in advance for the advice!


This is incredibly useful, thank you Simon.


Good article, can you give some examples of tailored cottons please?

I think a pair of Oxfords with a light hue, say a pine shade, can work with tailored cottons and chinos. Although have to pair colours carefully, the right green or brown but not navy blue.


Thanks for the link.

Normally I try to abide by the, informal, commonsense rules. But there are some items, shoes or otherwise, which are favourites/signature items, due to quality, appearance or heritage, which convinces me that I can wear further afield. Less about discipline, more the heart ruling the head.


Definitely. I’m fairly sure I’ll drift more in to the fold over time. Much as I like classic menswear, they can be, deliberately, narrow confines within which to operate. So the contrarian in me likes it when I see people challenging or breaking the rules, especially when done well.

Gary Mclean

When you say about chinos “There is an American style that involves wearing jackets with chinos and it can look good, but it’s quite specific (roomier jacket etc). Most of the time chinos aren’t the best with a jacket, and should be kept to more casual partners.” Please can you go into more of the specifics about successfully pairing chinos with a jacket, considering for example if a patch-pocket garment-washed cotton Boglioli jacket would be suitable, even if it is fitted and darted? Wishing you every success with the web site. It’s great to see the website evolve and stay relevant over the years, whilst always being high quality advice.


my opinion would be a fitted and darted jacket would not work. something like a Drake’s games blazer can work.


hi simon can i ask what shirt you are wearing in the very first picture with the white/cream trouser? Looks like a white linen with a one piece spread collar? It looks very good


A perfectly timed article from my perspective. I am moving jobs and no longer have to be suited every day. It means I need to build out my separates. Can anyone recommend a store for high quality RTW flannels in London? I have already tried Anglo-Italian, but was wondering who else to visit.


Fantastic! I’ll look forward to reading it.


Thank you, Simon
I’ve struggled purchasing chinos in the past, usually using brands like Hackett, Gant and J.Crew as they fit best off the peg. However, their products contain 2% elastane which I’m not keen on as it clings to my thighs and doesn’t wear well over time.

I’ve been looking for 100% cotton chinos and have found Tailorstore do a 100% cotton twill with custom sizing. The price seems quite reasonable, do you have any thoughts on whether its a sensible purchase.
Thanks again

Ian A

Depending on what type of Chinos you desire if you want smarter RTW Chinos I’d suggest going to somewhere like Cordings for 100% cotton. Or going to Son of a Stag if you wear your chinos with t shirts sweatshirts and sneakers suede shoes etc for a casual option.


Hi Simon,
Great article yet again. You’re a great fan of grey flannel trousers so I was wondering if you have any recommendations for these in RTW or MTM (I can’t stretch to bespoke)?


Hi Simon- one thing I wanted to also suggest to folks on MTM trousers is not to be afraid of buying cheaper ones and then having them altered. Just like you did with your Rubato chinos – I’ve found it perfectly possible to change the line/style of Cordings or others. Now I mostly focus on the fabric and then alter the waist/seat and line accordingly

Peter K

I have a pair of flannel trousers from the online brand Spier and Mackay that I am very happy with.


Hi, Simon! As always, a very useful piece with sensible advice and an easy ‘cheat sheet’ reference for all the trousers. I can see myself coming back to this one often.
I do have one point that I’m unsure about. You say that tailored cottons should not be worn with a smart blazer or a fine knit, but I’m not so sure based on my own experience. For instance, I have these single-pleat trousers from Cavour in stone and a flat-front pair in a much lighter and almost transparent fine beige cotton similar to this one and I have worn both very successfully with fine knits such as cotton and wool knit polos, fine merino cardigans, and also my dark navy blazers with gold buttons.
I do probably wear them more often with more casual jackets (wool-silk-linen, open-weave wool, tweed), but not as often with less fine knits, particularly the beige pair as it is a summer cloth so I wear only fine knits with it unless wearing a shirt. In my experience, I haven’t seen any issues in matching the formality of the tops and bottoms in those combos, with the former pair because it is a moderately slim single-pleat with turn-ups and side-adjusters, and with the latter mostly because it is such a fine and soft cotton that it almost looks like beige wool until you’re up close.
Another small ‘disagreement’: I think chinos can work well with jackets if the jackets are clearly not in smart materials and are ‘plump’ looking, such as e.g. Donegal or herringbone tweed or a fluffy cashmere. I have pulled it off with brushed cotton chinos in brown/mushroom, very dark navy chinos and mid-beige taupe ones. Your point on the American-style chino+blazer makes sense to me, it can be done but only under specific circumstances and the right fits.


Thanks, Simon! You did mention spectrum overlap indeed.
Fair point on fit and your own tweed jackets, could be that my experience is based on my RTW jackets in that fabric. I think this ties in to context too – a tailored tweed worn in the city would be matched with tailored trousers and worn more for style and love of the fabric (or warmth), while tweed in the country and for more active pursuits (out and about on the town, walk on a forest trail…) needs less of a close fit and is used in a more ‘utilitarian’ or deliberately more casual and ‘shabby’ context, lending itself to more casual and therefore less-well-fitting trousers.


P. S. As reference, my beige cotton dress trousers look very much like these trousers of yours, from a distance:


Don’t get the chinos + jackets slander, it’s a modern day classic imo and quite often as smart as you can go if you want to wear a jacket without looking out of place these days


Please don’t take me seriously I was attempting to be light hearted x I think as long as the chinos are of the smarter variety and a neutral colour like beige or grey it works, esp with a classic navy hopsack or similar. But even more casual styles could be pulled off, kinda like in your last pic with the off-white jeans – they could probably be swapped out for chinos in the same colour and it’d still work


Btw, if I can pick the PS hive mind for a sec, has anyone come across decent rtw linen trousers below the £150 mark? They’re unbeatable for versatility and comfort but I can’t seem to find a budget friendly option to save my life

Christopher Lee

Try Spier & Mackay, Matt.

Rowan Morrison

On chinos – apart from the “American style” you mentioned, would you just advise no tailored jackets with chinos, ever? I just ask because I have always assumed it was fairly standard practice (perhaps due to having seen the American style you mention) but have tried it a few times and it never really feels right. I know you get chinos in different levels of smartness (slimmer cuts with hidden stitching/seams being more smart) but are none of them really great with a sports jacket? Even a tweed jacket or something equally casual?

Jim Bainbridge

This is a look I like, but I think it only really works if you do it in that devil-may-care insouciant Ivy way – and it helps to combine with other like elements – blue OCBD, beef roll penny loafers, white sports socks, Shetland jumper under the jacket, etc. (but without looking like an RL catalogue model!)
So much of this is association though, and therefore very personal and subjective – the idea of making a finer, slightly dressier version of what were originally army trousers, makes no sense to me personally, for much the same reason as slim and pointy penny loafers, lightweight tweed hacking jackets that definitely couldn’t go shooting, or a motorcycle jacket that you couldn’t wear on a motorcycle. Etc. The “authenticity” is what legitimises, at least for me.


Good article. I tend to agree with most of this but never thought about categorising the different types of wool trousers like this as clearly as you have.

Trousers seem to be one of the most overlooked items for people that need to dress smartly without wearing a suit. I see lots of people wearing casual chinos with smart shirts and jackets, or plain worsted trousers (not as part of a suit). In both cases it just feels unimaginative when there are much nicer and more interesting options that could be worn.

A question: are there any types of wool other than high twist that are suitable for separate warm weather trousers? I have tried high twist and really struggle with the scratchy texture. I am considering trying Crispaire and Drapers 4ply based on your recommendations when I asked a question about suiting fabric on another post but getting MTM trousers in an unfamiliar fabric to see if I find it comfortable is an expensive experiment.


I think the issue is that the sort of shops the average person shops at only sell worsted suit style trousers, chinos or jeans. To get more options like flannel, cavalry twill, cord, linen etc you normally have to go to more niche menswear shops or go MTM / bespoke.

Thank you for clarifying that point about high twist wools. I thought they would all be some degree of scratchy but if Crispaire and Drapers 4ply are not then I might give one of them a try. I find dressing in winter so much more fun because you have a wide array of comfortable drapey fabrics to choose from (not to mention the opportunity to add lots of layers to outfits), whereas summer fabrics always seem to involve compromises.


This is an incredibly informative post, Simon. I love the 50,000 ft view of all trousers. Am I correct in inferring from this post that both worsted and superfine worsteds can be used for suits, but only superfine worsteds are appropriate for standalone trousers? Thanks so much!


I just noticed Kit Blade is an advertiser. Their website doesn’t offer much information about the company. Can you offer a comparison of their products to other pant makers that readers of this site will be familiar with? Their offerings look intersting, but with so little actual information, one is reluctant to try. Thank you.


Hi Simon, A very good benchmark to concentrate the mind in choosing an outfit. I’m sure we all put something on occasionally & look in the mirror & think sometimes “ does this look quite right” without being able to figure out why; although I think PS readers will do it better than most.
Flipping it around with shoes & trousers what’s your take on brogue shoes & your selection of trousers?


Hi Simon. would the W&S chinos be smarter than most chinos and be appropriate to wear with tweed jackets?


Thanks for your reply. For a tweed jacket, regimental stripe tie, and Oxford button down shirt, would corduroy or cavalry twill trousers be the best choice?


Hi Simon
I suffer from very naturally skinny legs in comparison to wide shoulders and a small waist.
I find that odd jackets and trousers seem to accentuate this in an unflattering way – broadening the shoulders but then trousers making my legs look even skinnier.
I can’t work out how you and others achieve a nice drape without the trousers swishing around and making the problem even worse. Is it something to do with picking heavier fabrics? Avoiding either too wide or too skinny leg lines? Any help appreciated.


Usually Incotex flannels/chinos. I got most of them in 2018 or so, when slimmer cuts were very in vogue, stopping a bit higher above the shoe with no turn-ups. I think that may be part of the problem


Hi Simon,
Thanks for the very useful piece. Like others, I’m wondering about your advice on chinos and jackets. Would you no longer wear this combination?
It didn’t strike me at the time as a clash in terms of formality – and it still doesn’t.
I sometimes wear Incotex chinos with a jacket. It doesn’t feel off. But perhaps those chinos are sufficiently unlike the workwear kind of chinos. I seem to remember you wrote a piece on the different types of chinos once, but I can’t find it.


Thanks Simon. That Rubato review incudes this useful thought on ‘smart’ chinos: a combination “works OK when the jacket is soft, undone, and worn with some slouch.”


Thank you for this article—it’s really useful. Where does a relatively casual coat in donegal fall along this continuum? Maybe with the flannels, or a peg higher with cavalry twill, if the cavalry twill is in a somewhat casual color?


What about fine knitwear designed to go with tailoring, like a Dartmoor? Is that formal enough to pair with cavalry twill, and maybe a refined tweed?

I have a similar question regarding worsted flannel. It has a bit of a sheen, and certainly is more formal than flannel. But I can also see it being paired with something like the Dartmoor, especially if the trousers are in a casual color, like brown. Could a particularly refined tweed work with all of that?

Matt S

Nice overview of common trousers. I will disagree with your placement of wool gabardine above “regular worsteds”. Gabardine has historically been a sportier material than the “regular worsteds” like serge, prunelle and plain weave. Though gabardine suits are a thing, gabardine trousers don’t have the “missing suit jacket” look of the more common suitings. Because of its defined steep twill wale, I think of gabardine as akin to whipcord and cavalry twill for warmer weather. It’s the classic sporty trouser for classic spring/summer jackets, like the hopsack blazer. It’s what men had before high-twist wool was a thing. I don’t see it being nearly as smart as mohair, which is used not only for fancy suits but also for dinner suits.

Matt S

I understand what you’re saying. A lot of the gabardine I see these days is 240-260g, which is very lightweight, smooth and shiny. It’s usually in cream or earth tones, which dresses it down. I found a picture of Ralph Lauren Purple Label navy gabardine trousers, which certainly look dressy. In the picture they hardly look different than my midnight blue mohair dinner suit. But in the tan and cream I’d say it’s less formal than a grey serge, and definitely mohair in any colour. I can’t imagine a formal suit in this cloth. Huddersfield Fine Worsteds has a more traditional 340g gabardine, which resembles my older gabardine trousers. It has texture, but it’s sleek. It’s shinier than serge and plain-weave worsteds, but it’s also so different from them. I’m used to thinking of it as a sporty trouser despite its sheen. It’s what I was raised on for odd trousers for warmer weather.


What types of jackets do you feel go well with cotton tailored trousers? Do you feel they have similar problems as chinos matching jackets?


Thanks. What are these trousers mostly at home with? Knitwear? Casual shirts? And maybe more casual items like your linen overshirts, Harrington or suede jackets?
And loafers at the bottom?
Thanks again


Do charcoal flannel trousers go well with dark brown shoes, or would it be better to combine them with black or color 8 shoes?
And for charcoal flannel and linen trousers, do you favor single pleats and turnups, or flat fronts and no turnups?
Thanks again

Joe P

Hi Simon, I hope you don’t mind this quite specific question. I’m looking to expand my trouser range: materials, colour, etc. I’ve a fair few already, and my budget isn’t limitless, so I’m looking at the Berg & Berg sale. Quite taken with their cavalry twill in cold beige and their sand flannels, as I don’t own any CT, or flannels in that colour. But would you say they (especially the CT) fall into the ‘old man-ish’ category, in terms of colour-and-material combo?


Hi Simon, do you think ecru/white canvas sneakers could work with dark brown corduroy trousers?

Many thanks,


As regards shirts, could i assume that casual shirts like linen and linen cotton shirt which works with tailored cotton trousers can work with chinos?


Hi Simon,
You wrote that “oddly, I think some leather shoes work better with jeans than chinos. Eg a tan derby” I am a little bit surprised by this, what other leather shoes and colour do you think would work with jeans? Tan leather penny loafers perhaps?


Well It’s weird that I’ve been wearing tan leather tassel loafers with jeans mostly with off-white T-shirt and light wash jeans combo for months. They look good in my eyes. for chinos? Umm probably something like cream or beige would be more appropriate.
I try to limit myself to have 8 shoes only that are appropriate to wear in a tropical country, 8 shoes that I can wear with jeans, high-twist wool suits, linen suits. Here’s the list and it’s inspired by your “If you only had five shoes” and please feel free to correct me and which shoes should be better to get:

  1. Black leather cap-toe oxford
  2. Dark brown leather cap-toe oxford (no broguing)
  3. Black leather penny loafers
  4. Dark brown suede penny loafers
  5. Tan leather tassel loafers
  6. Dark brown suede chukka boots with thin rubber sole (this potentially could be my best friend with lots of jeans colour)
  7. Derby??? Probably a pair of split-toe derby in black suede because I like the rarity of black suede. Still not sure how to wear them though.
  8. Either dark brown suede split-toe derby or tan derby