grey herringbone jacket robert redford

Dear Simon,

You have written eloquently before on building a wardrobe aimed, I suspect, at the young city-based professional wanting to start to explore the world of good quality RTW or bespoke tailoring. My question is slightly different.

Over the last 40+ years I have built up a considerable but disparate wardrobe of good quality clothes – not all bespoke by any means. Now, as I near the age of 60, I want to ‘downsize’ my wardrobe and start to rebuild it with a limited style and colour range – to almost create a ‘uniform’ which I can wear – with variations of cloth weight – summer and winter. I would not necessarily want this ‘uniform’ to be a formal business suit as I do not have to wear one regularly to my office and I live in a rural part of the UK.

Is there a jacket style which I could adopt which could be worn casually or with a tie for business meetings, more formal occasions etc? Jackets and trousers would be bespoke but matched with good quality RTW shirts from Margaret Howell or similar. Shoes a mixture of good RTW (Lobb, Edward Green) or bespoke (Amesbury).


Dear John,

It’s an interesting question – similar, in some ways, to the one we often have to ask ourselves when travelling. You have to create a capsule wardrobe where, ideally, all the constituent parts match with each other and can be swapped around to create variation.

I would encourage you to start with a couple of well-made jackets. The most versatile colours would be navy and mid- to light grey. The navy is most useful for the dressing-up you mentioned. With the right pair of trousers and tie, it is almost as formal as a suit. A grey herringbone, on the other hand, would go with everything from jeans to flannels.

Begin with those two jackets and then put together 3-4 pairs of trousers that go with both of them. My post on odd trousers should be helpful here. I would suggest, as a starting point, that you look at cream, tan, grey flannel and charcoal. Substitute one of those for jeans if you wear them. With the grey flannel, the key is to make sure the grey is sufficiently different in tone to the herringbone jacket.

Next, two great pairs of shoes. Go for dark brown and tan. Brown dark enough that it can go beneath charcoal. If you are unlikely to wear cream trousers, then the shoes could be mid- and dark brown.

Add in a couple of crewneck sweaters – in say bottle green and navy – and you have a pretty flexible wardrobe. The navy blazer, charcoal trousers and dark shoes will be pretty formal with a dress shirt and tie; the herringbone jacket will be pretty casual with cream chinos and tan brogues.

I hope that helps. If you’re going bespoke, a Neapolitan construction from someone like Solito or Caliendo will help a lot to bridge the gap between casual and formal.


tan corduroy jacket
Corduroy would be a – slightly more casual – alternative to the grey herringbone


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Paul Weide

Great photo of Redford from “Three Days of the Condor.” Underscoring your point (with a clever nod to the earlier role), 26 years later Redford wore a similar French blue shirt and grey herringbone jacket combination in “Spy Game.”

Matt Spaiser

Hi Simon,

You’ve written a lot about the versatility of navy and light grey jackets. I’d like to get a navy jacket in addition to my typical worsted blazers with metal buttons. Can you point me to articles about your navy jackets? I’d love to see what you wear to get ideas.

Matt Spaiser

Thanks. I found the travel blazer, which is similar to the blazer I have except for the pocket styles. I look forward to seeing your navy cashmere blazer. What do you think of navy tweed, in herringbone or donegal?

Matt Spaiser

I agree that they work well in grey, and that’s what I’m used to seeing. I have a medium grey donegal tweed jacket and a medium grey and cream herringbone camelhair jacket. I’d like to get something else in navy, but I don’t want something as delicate as cashmere, nor do I want another blazer with shiny buttons. I have smoked mother-of-pearl on my navy hopsack blazer, which looks like metal. Maybe doeskin with horn buttons?


Very interested in the grey odd jacket debate. Two questions for Simon (and Matt if he’s still following):

1. Would you recommend any books for a soft, light-ish weight grey that would work as an odd jacket (not looking for a heavy tweed herringbone or donegal, but the rub is finding something sufficiently casual to avoid the half-a-suit issue; glen plaid with overcheck is not sufficient in my view).

2. What are your preferred odd trousers with the grey odd jacket? (I’ve read your general post on odd trousers.) Do you think navy cotton drill can ever be made to work? The consensus at StyleForum is not, but this may be groupthink.


Very helpful, thank you. Harrison’s Moonbeam is an excellent suggestion. Your Cifonelli DB is lovely – exactly the sort of thing I am looking for cloth-wise, in SB with soft tailoring. I suspect it will have the feel I am looking for without the cost of cashmere. Was your DB 36654? (


I’m in a similar state to Matt in this comment thread.

I’m looking to commission a versatile jacket/blazer for casual wear and weekends, never the office. I’d like it to be 4 season (excluding hot days, and requiring layering in winter), and really be my go-to casual jacket. Longer term, I think I would supplement this with a warm weather jacket (fresco or silk-wool linen) and a cool weather jacket (e.g. cashmere) to create a second option for any time of year.

I’m unsure which cloth to pick. I’m thinking maybe a navy hopsack.

Would you recommend navy, or would a light grey (which you seemed to favour above), muted brown, or oatmeal be better?

And is hopsack the right cloth? You suggest above that cashmere might be more versatile. Would that still be true if I intend to wear it during spring and cooler summer days?


Dear Simon,
If I had to add a couple of shirts to the list, what colours/fabrics should be included please? Really appreciate your sage advice!

Eric Mavor

I rather like the corduroy jacket in your article, do you have any idea as to the maker?


Hi Simon,

From a perspective of formality, is a mid-gray plaid suit the same as a blue plaid suit?

The idler of march

Just my thoughts on this, but if I was seeking to create a ‘uniform’ – a set of clothes that all work well together – I’d probably start by staring at a colour wheel for a while and planning it from there. If you can pick out one colour scheme, eg max five colours, that work well with your hair colour and complexion, then you have the start of a look which is consistent and where the items have a high degree of comparability with one another. Colour (rather than texture/fabric/level of formality/countryside vs city) is the one thing that is really going to determine whether you can use pieces together or not so should perhaps be the primary input into the process.

John K

Thank you for your reply to my original question. Your Caliendo Neopolitan Tweed Jacket would be a good starting point for the jacket style. Hopefully I can get my usual tailor to make something similar – though perhaps slightly less ‘waisted’. I shall probably restrict my colour range to navy, charcoal and grey. I admire the discipline of those like the British actor Bill Nighy who seem able to wear a navy lounge suit (or similar) exclusively but doubt if I could resist the attraction of a different but complimentary colour.


Hello Simon

Can corduroy jackets be altered normally like wool jackets (sleeve length, take in the waist). One older salesman told me this can be a little harder due to jackets being thicker. Is corduroy mostly in RTW or does is exist in MTM, bespoke?

Matthew Acton

Hello Simon,

Could you give your thoughts if a blazer can be successful altered from a 44 to 42? Online opinion I’ve read suggests that 1 size down shouldn’t present a problem……

If this is the case, do you have any suggestions where in the London area could carry out this work?




Dear Simon,

I would have a question not directly related to the post above, but maybe indirectly so: I have been quite busy in the last seven years or so to build up a wardrobe myself, with investments that will certainly not reach your levels but were still quite substantial from my perspective. And obviously once you start, it’s hard to stop; and there always seems to be something, even something very classical, that one does not have but which does look really great on some pictures: This kind of odd jacket, those country leather boots, that tweed suit, and so on. And even though I have benefitted massively from some of the advice on your website and in other places, and have tried to keep in mind to always consider when I would wear certain things, in the end I have ended up with some items that I thought I need to have, and then I kind of find out I do not wear them. Long story short: I take it from some of the posts that even you may not always have fully escaped that trap, so I was thinking it might be helpful if you could share some insights about your experience with items that the strive for sartortial completeness (if that is a combination of terms that makes any sense) seems to require but that will most likely end up just sitting in the wardrobe of the modern urban citizen.


PS – Sorry for potential posting this twice, I was not sure it was taken on the first time as I forgot to enter my name.


What a great site and a great thread – I’m beginning to wonder where I’ve been all my life.
As an elegantly ageing hipster that turned the page on corporate life a while ago, I have had great fun undergoing exactly the ‘downsizing’ that John refers to in his question and can’t exaggerate the importance that corduroy can play in the transition.
I had Anderson & Sheppard make me a mid blue single breasted corduroy suit in a thin wale and it’s turned out to be the most complemented and versatile piece in my wardrobe.
It has a multiplicity of uses. Is great for all but the most formal occasions. Looks fabulous with knitted ties or with a light slipover seater. Is also great for traveling in and even looks good creased!
I love it to bits and would like to be buried in it providing, somebody has the foresight to slip a flask of Talisker into my pocket. Seriously, such is the depth of my love for this piece, I have a jacket with a broader wale currently under construction by A&S.
One last piece of advice on the wardrobe liberation is the importance that Chelsea boots can play. Particularly in suede. Tod’s do a great pair.

Rob O

Hi David, that suit sounds particularly interesting. I would love to see a picture if you would be so kind to share. I was watching Bryan Ferry on Jools Holland’s excellent show earlier this week. It appeared he was wearing a (slightly loose) Andersen and Sheppard suit in moleskine. His boots were probably Lobb although Simon might correct me there.

David Craggs

Yes Rob – I think you are correct, Ferry’s suit looks to be A&S but I suspect it’s velvet rather than moleskin.
Ironically, it is the exact same colour as one of the cords they made for me.
I’ll have my son take a photo of it and post it next time he’s around (I’m technically challenged).

Ben Johnson

If you’re trying to build a smart casual capsule wardrobe, what about the option of getting a grey flannel suit in a casual cut, then having the option to wear them together or separately?
Or do you think it’ll be better to get a grey tweed or cashmere jacket with a separate pair of darker grey flannels?


Dear Simon,

I want to improve my wardrobe with some jackets and shirts, especially for the coming spring and summer. Bespoke offers mostly the best quality, but can be quite expensive. Actually I have invested in some bespoke garments, but I can not effort the money to build my complete wardrobe with bespoke items. Do you have any recommendations for RTW, which offers a good value for money?



Do you think a jacket in a gray herringbone is more versatile than in a gray Donegal?


Hi Simon, I am looking to get a grey sport jacket made in Moonbeam but cannot decide on the right shade. Which shade is more versatile 36655 or 36656 ? Much appreciated.


Hi Simon! I’m not sure if you remember we met at the NYC signing of The Style Guide at the Armoury; I had to wear a mask for health reasons. I’ve been looking into getting my first bespoke made up in Hong Kong for around HKD8000. I’m heading into dental school and I expect to be wearing trousers regularly with an odd jacket when not in my white doctor’s coat, with suits only for events. As such, I’m thinking of commissioning a suit that is intended to be worn as separates with the primary aim of versatility with Neapolitan construction and patch pockets. I’m thinking of sticking within the realm of textured solids and was considering an oatmeal twill similar to your Caliendo jacket but without cashmere for the trousers. Alternatively, a light grey flannel or donegal/shetland tweed. Any suggestions or complications I may not have considered ?


Hi Simon,
I notice you advised specifically crewneck sweaters. Why is that? Why not a V-neck, or a shawl collar?


Hi Simon,
Can I wear cream trousers in cords, chinos or in heavy twill cotton during fall and winter? Should they be worn only when the weather it`s sunny ?except when it`s raining .And can the colour be worn in the evening in a casual setting?


So cream it’s out of the question for evening. But what about cream trousers in corduroy during spring? Normally during spring in my country temperatures are around 20-25 degrees even this month was around 20 degrees. Trunk has some 5 pocket style . Can they be worn at this temperature and in spring? Thank you Simon


Hi Simon,
Do you think that these cotton trousers could be a substitute for a chino ? They are garment washed and look smarter than a BHL chino but can they work in a casual wardrobe?( Wearing them without sports coat)


What brands for cotton trousers do you recommend that could work casually? Other than stoffa because I can’t have an access to them. Thanks


Hi Simon,
In what style would you get each jacket and are there any details that you would get for each jacket?


I actually am a student working on an industrial engineering degree. I was looking for something that’s really middle of the road where I can dress it up and dress it down without it looking off.


Hi Simon,

I had seen, in the herringbone donegal overcoat, that herringbone that looks like a texture is more formal. I was wondering if I could match the formality of the grey herringbone with navy and if so, how would I do it just based off of the fabric itself?


I mean that I want to match the formality of two jackets that I want to have in the future. They will match in terms of construction but I am wondering if I can have the fabric’s formality of both jackets match. My apologies about the confusion.


Hey Simon,

I was wondering if a solid grey tweed jacket could replace the grey herringbone? If so, how dark would you recommend the tweed jacket be?


Thank you Simon. I would imagine that the herringbone jacket would draw more attention, correct? If so, would a smaller pattern draw less attention?

Lindsay McKee

I just love the Wardrobe Building Series in particular, referring back to it many times as I also love the wider Guides series generally with many unique articles…but it always thrills me when a new article is added to the guides series which are so informative and give tremendous advice to all !!!

Many thanks Simon!!

Lindsay McKee

Simon,I don’t wish to be naive but what is the distinct difference between a jacket and a blazer?
I don’t even have one🙁
I think that needs putting right!
I adore this post as stated already.
Unbelievable but I’ve too many silly coloured socks and polo shirts and the same in knitwear. I’m starting to sort out the latter two.
My heart prefers belts over side Adjusters which feel a bit “off” unless used with braces, but that’s me, others may differ here.
I’ve found some beautiful belt makers,some employing oak barked tan leather from J & FJ BAKER in Devon… sounds exquisite!
I just want the bare essentials in my wardrobe but quality essentials. Mega declutter!!
I don’t wear jeans for instance.
I am a smart casual to formal dresser and casual in 3rd place.. put it that way.