Caraceni grey herrinbone cashmere jacket

Last week’s explanation of how I put an outfit together seemed to be popular, so let’s try that again.

This outfit is simpler than last week’s. There are fewer colours, there’s no tie to worry about, the handkerchief is plain. But still, there is a clear process and choices at every stage that are worth exploring.

As before, the process started with one thing I wanted to wear: my Ferdinando Caraceni cashmere jacket. (I’ll do a separate post on that on its own on Friday).

I wanted to wear it quite casually, but its construction means it is too formal for jeans and probably chinos. So in order to be similarly casual, I went for an open-necked shirt.

Next, I wanted the shirt to bring the outfit away from being too smart or corporate. My two favourite ways to do this are with a grey or denim shirt.

Ferdinando Caraceni jacket and Simone Abbarchi shirt

Denim undermines the smart/corporate aspects of tailoring because it takes a common shirt colour – blue – and it gives it an unexpected texture and variety in tone.

A pale grey shirt does something similar with tone, as an alternative to white. A mid-grey shirt (like this one) achieves that immediately by being simply darker than any formal shirt. And its lack of saturation means it works much better than other dark colours.

Trousers. Navy chinos might have been OK, but as I said more formal materials feel better with this jacket. Lightweight flannel therefore, and navy often looks too smart as an odd wool-trouser, so brown, tan or green are the general options. Brown felt better for the subtle, sombre effect achieved elsewhere with the jacket/shirt combination.

gaziano girling bespoke shoes

Shoes. Not easy with brown trousers. The options are black or very dark brown – so dark they achieve the same level of contrast.

These, my Gaziano & Girling bespoke Adelaides, aren’t quite that dark, but the contrast in the patination, with a virtually black heel and toe, is sufficient.

Finally, handkerchief. Cream linen, as last week, would have been less formal, but I felt overall the outfit needed a little more contrast, so white (from Anderson & Sheppard) won out.

The shirt is my Simone Abbarchi (again, separate post on that soon) and the trousers are a Vitale Barberis Canonico flannel made up by PA Crowe.


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Did you manage to sort the issue with the Crowe trousers (something to do with how they fell at the front?), how much were they and would you recommend Crowe more generally? Have to say they look excellent in the photo…

Nick Inkster

Suede might also be an option. I have a pair of snuff coloured loafers which I often team up with dark brown moleskin, and they sit together rather well.

fred b

Simon, the height of your shirt collar strikes me–I like. How high or what is the measurement here? Thank you.


Appreciate these article themes and the eloquence with which you describe the choices but this doesn’t work for me.

Individually, all covetable items. The shoes in particular are spectacular. However, i find the cream / off-white linen has a jarring effect, it cuts across, it stands alone and draws disproportionate attention. It is conspicuous. An outfit should appear as a cohesive whole without one element or aspect drawing too much attention.

I understand you are trying to casualise your outfit but aesthetically i can’t behind the grey shirt and grey jacket combination; it is all…well too ‘gray’. The denim shirt would have worked much better here.

Not one of your finest, IMO, Simon.


‘the formality of different linen handkerchiefs in…’

Sounds like a fascinating post, Simon. I’d be looking forward to it.

Paul, it might just be a hankie – and i like the hankie on its own. Just not with this ensemble.


The colour scheme inverted would look better.


Hi Simon,
A very good idea to submit again an exercise in style! I hope many PS’s readers will chime in. There are two tricky issues, you have rightly pointed out, that are not at all easy to handle: 1. How to achieve harmony and consistently maintain the same level of formality for a whole outfit, knowing that the first piece of choice somehow dictates the two aforementioned parameters, which are to be taken into account? Personally, I agree with your choice of the trousers. As to the shirt, you still have more leverage, I think. And then, 2. the color of the … oxfords (worth bearing in mind)! Obviously, there are less options with brown trousers. One could hardly do better than what you did. Be that as it may, I would be interested in reading alternatives!


It’s just a hankie, Incognito. Cream goes with almost anything. Maybe another colour would have worked better. I think it lifts the dark outfit. Not sure Simon would say it’s the only possible option.


I see the photo was taken in London – St James’s Park? – but I hope isn’t wasn’t taken this week. The idea of cashmere and flannel in these temperatures is enough to give me the vapours. Or you are an even more especially cool customer!


This grey/brown combination is fantastic and will look great whether the jacket is grey and pants brown or the reverse. This color scheme is often ignored so, thank you Simon for bringing it to your readers attention. Of course this look you have on is meant to be a more casual look. Could you replicate the color scheme effectively for a dressier look that would include a tie?


very good,thank you.


Thanks for another great article Simon – really enjoying this theme. I agree that grey on grey is not an easy look to pull off. I have a similar reaction when I see pics of guys at the Armoury wearing navy polo shirts with navy jackets – looks cool on them but definitely requires mastery. Really like the idea of the brown trousers though – I have some brown brushed cotton ones (almost feel like moleskin) that are a very versatile colour but a bit too casual for more structured jackets. Might be time to order a pair…

(Those shoes are just stunning by the way!)


On a completely unrelated note, what are your thoughts on buttoning the jacket while wearing a three piece suit? I feel a bit stiff and bundled up with both the jacket and waistcoat done up.


Not one of your finest unfortunately, Simon. Definitely more student charity shop than anything else.


Simon. As a Crowe client. Those trousers look super – as you say re tailor client association, did you not get on with or see eye to eye with the guys there? F


Great article but not one of my favourite ensembles that you’ve put together. I personally don’t feel that the trouser colour goes with that grey jacket, which by itself is a fantastic piece. The biggest let down for me is the grey shirt on grey jacket. You recently pulled off the grey-on-grey look very well elsewhere with different attire. I think we were a little spoiled with you’re first bash at this type of analysis of garment selection with your tan jacket but I personally don’t think you’ve hit the same highs with this. The shoes by the way are magnificent…very envious!


I second that. Brown + grey are rather somber tones and put together seem dull to my eyes. The white pocket square softens it up, but as a whole I feel this combination does not do good to the wearer (his skin tone etc), although I certainly appreciate the exercise in refined understatement. I have the same objections with tan+grey, sorry. Perhaps a beautiful scarf in burnt orange might give just that splash of colour?

Noel Hutchinson

Hi Simon, nice outfit! You’re correct that shoes normally should be darker in colour than the trousers, but could you swap out the shoes you’re wearing with tan shoes? That is, to provide a contrast in the opposite direction and lend a more casual look, too, and whose lightness in the tan brings up the bottom of the outfit to match the lighter coat on top? Since you’re doing the light-on-top-dark-on-bottom approach?


I like it. I didn’t think I would just seeing the first photo with the grey on grey, but…it’s good! Not everyone’s taste but how dull it would be if it was. One thought – have you dropped the specs? I actually think they might have pulled this ensemble together quite well.

Harry Shipmann

Wonderful outfit, but I’m not sure the Brian Blessed tribute beard suits the whole ensemble. Can we have a return to the more manicured look please!


The tone of some comments here surprises me. Simon’s committing no solecisms in this outfit. Personal tastes will always vary. Has Style Forum blocked you poor dears?


With the exception of maybe one comment, the tone here has been fine. Besides, debate should be fostered not stifled.

Simon is a maven of style but he is not infallible. What he definitely doesn’t need is an army of sycophants circle-jecking. And it is a testament to Simon that he just didn’t offer universal praise.

Zapp Brannigan

Healthy debate is a good method to share and discover ways of pairing clothing. I find the comments as useful as Simons own viewpoint . I must agree with the above comment on the beard length though.

Noel Hutchinson

Thanks for the reply. Would burgundy coloured shoes work with this outfit (enough contrast)?


A quick question, Simon. I wonder whether the constrains would be the same, were you to wear the jacket in the evening. And what could be your main options?


A dark navy tie, for instance. By the way, interesting suggestion made by Noel Hutchinson: indeed, dark burgundy oxfords could work.

Noel Hutchinson

Last question about this: would a contrast in the shoe’s texture work, or not? So — a pair of brown suede chukkas that are the same in colour as your trousers (most chukkas aren’t darker), but would the texture work enough to counteract the similar colours in shoe and trouser?


Another good look. For me the grey on grey works well (variations on complimentary colour and cloth). The cut of the shirt collar is particularly fine. Cordovan or burgundy shoes would also compliment the colours, burgundy can be too red but over polishing with brown can modify the tone. The pocket square seems to have drawn interest, I think it looks smart but a contrast to the grey on grey might have added further zest. Burgundy paisley in silk (the shine of the silk contrasting against the cashmere matte) would work well against the grey. Orange or purple in subtle tones might also work but perhaps improved with a blue denim shirt as background.


I think that a blue denim type shirt would work well with the grey & brown and also a patterned handkerchief if one was needed would look more casual than the white/cream one. Thanks for providing these examples and putting yourself out there to be critiqued! One question: how do you find your flannel trousers in terms of keeping their shape?


Simon, I’m really enjoying this feature. You should perhaps consider making it a regular item; it’s interesting to see how you are making use of your bespoke purchases. On a different point, I’ve recently had a couple of tebas made up in linen by Justo Gimeno (one in a similar shade of green to your safari shirt) – I know that you’re not a particularly big fan of tebas but I’ve found them very versatile. Keep up the good work.


Dear Simon,your shoes,as always,look very elegant.May I ask a question?In order for your bootmaker to achieve that elongated refined result is there a one inch gap remaining between your big toe and the tip of the shoe.I ask this rather eccentric sounding query because I have noticed that to obtain the necessary wiggle room for one’s toes, the width of the shoe makes it necessary to elongate it’s length to produce an aesthetically satisfying result.

Adam Jones


Could I possibly have your opinion/ Advice

I get married next year and I will be commissioning a suit, nothing over the top. Dark blue – not navy, two button 3 piece. But the whole question of bespoke vs. made to measure comes up.

The reason is, I have a budget for bespoke, not the Row but The west end and City. My thoughts have been with Thom Sweeney. The problem is I have a huge gap of quality tailoring in my wardrobe. I am upgrading my shirts (I have an appointment in September with the guy you recommended) but have very little in the way of good quality tailored jackets.

Do you think someone would be better off spending the money on a MTM suit and a MTM jacket, rather than just one great bespoke suit I may only wear 5 times per year – I don’t currently wear suits to work.

The TS block seems to fit me well and The guys at TS who I have been dealing with seem to think we can get pretty close to a perfect fit based on the trial jackets I tried. I even ordered a Mr Porter RTW sample to test this and bar a bit of shortening the shoulders neck fitted well, very straight lines on the shoulders and a really clean back. I thought about having both or one done bespoke at graham Browne but I have to be confident they can give me the TS look and house style. That’s the style I like and flatters, Shorter jackets slimmer trousers and nipped waists with a slightly lower buttoning point. These aren’t normally the forte of a city tailor although their bespoke costing is similar to MTM somewhere like TS, G&H etc. I know from the post re your brother in laws suit you have some recent experience here. Albeit not your own.

I guess what I am asking is bespoke worth it for someone who needs more quality tailoring, not just an upgrade from a wardrobe of decent quality RTW or even MTM. The shortage of tailoring I have is especially jackets. I have invested in good quality trousers and shoes, RLPL, incotex Gaziano Girling etc. these have been what I needed. Now I need to fill the gaps!

Thank you in advance for any opinion you can provide.


Hi Simon

Two comments on the same jacket in one day. I too would encourage you to keep this series up. It seem you will get quite a bit of stick over the details, but I enjoy the way it makes me think.

I found myself thinking maybe you didn’t have quite the right trousers or shirt that you really wanted to work with this. I somehow (enviously) assume you have an infinite wardrobe that lets you pick out the colour, fabric and cut of any item you want, but I guess that just can’t be true unless we have a warehouse sized wardrobe. I often struggle with this, e.g. having a poplin shirt in the right colour and collar but wanting a linen shirt for the texture, or having the right colour shoe in an oxford but wanting a derby to dress it down etc. Do you find you feel constrained in this way, or do you have “enough”? I wonder how many options someone needs to feel they can put anything together, or maybe we are all too perfectionist over these details!


Hi Simon,

I think the whole outfit looks incredible. Amazing play of textures and colours. I do have one question: Do you think that you are more likely to pull off the grey on grey, monochromatic look if you are bald headed? I have dark hair (almost black) and olive skin and I feel that this combination would surely suck the life out of my skin colour.

Mark Lowe

Hi Simon,
I admit I’m not completely sold on the grey shirt-grey jacket either. Perhaps if the shirt was a touch lighter or a touch darker. It seems too ‘matchy’ to the jacket’s grey. But that’s just a matter of taste; I wanted to ask for more details on the shirt in and of itself. I am particularly taken with the softness of the edges, lack of placket, and the weave, as shown in the lapel closeup in the post on the jacket. Gives the ensemble the casualness a crisper shirt would not.


Lovely outfit Simon.

What other trousers would you pair the jacket with?

I might have a chance to get something similar

and would love your thoughts on what odd trousers would go well with it.


Would you consider an Oxblood shoe as an option for the trousers?


Hi Simon
Happy to have found this as I’ve got some brown flannels being made up to go with a grey wool herringbone jacket. Perfect!

In other thoughts, I’ve been looking at the reverse of this outfit, having a brown glen check jacket made to wear with mid-grey flannels and started out looking at wool/tweed but flannel came into the equation. I have some nice Minnis swatches that work pattern wise but am concerned that flannel over flannel offers insufficient texture contrast. So, can flannel over flannel work? Suspecting not, wear it with chinos instead …
Final worry, does flannel make a nice sport jacket anyway or best to stick to wool/tweeds?
(PS, apologies if this comes through twice, DNS error first try)


Thanks Simon, disappointing but as I thought.


Hi Simon – couldn’t think of where else to comment so this seemed a good place.

What are your thoughts on pairing dark brown trousers with burgundy shoes? I recently made up a pair of trousers in a textured wool/linen blend from Solbiati and was wondering what I could pair it with for a casual look. Burgundy suede loafers seemed a good idea as dark brown suede shoe/boot might be too similar in tone.


Never would have considered the grey/brown combo, but it works quite well.


Simon, concerning the shoe color, why wouldn’t a lighter shade of brown shoe work with the pants? Is it because there’s too much contrast? I mostly wear dark brown shoes, but have a few pair of lighter brown shoes as well. I realize that this is perhaps a bit of an esoteric question, but I think it’s a relevant one. Should lighter shades of brown shoes only be worn with a similar, or lighter,color brown pants in your opinion?


Simon, how did the trouser colour work out for you in a long run? I tried it, but I find it too dark. It doesn’t really work with all that many brown shoes, and black narrows the other choices. It doesn’t really go all that well with many staple colors on top, such as navy, burgundy or bottle green. And of course you can’t wear dark brown jacket or sweater either. Dark brown is beautiful, but probably not as good as, say, russet brown cords. It’s just a few shades, but it opens up so much possibilities.


Black? Really? It did not work for me at all. For me it works mostly with sweaters, sweatshirts and coats, in the grey/beige/brown/olive palette. It’s nice, but more of a niche choice. I tried the navy top/brown trousers pairing, but it just doesn’t look right to me.


Hi Simon

Beside of grey jacket,
Can you share more about the dressing combination on brown flannel trouser? especially dark brown.


Hi Simon- do you think this outfit might have worked with black shoes (loafers, boots, derbies?) and something with more contrast under the jacket – a black knit, a cream shirt or something? Grey/grey seems a little “flat” to me – I can’t work out why it works here.


Hi Simon, what colour of socks would you wear with dark brown shoes and trousers? Would you say dark brown or dark olive socks would be the safest option if there are different colours on tops such as navy or burgundy?

Many thanks,