Anderson and Sheppard jacket with denim shirt

The question I get more than any other – from both readers and friends – is how to wear separate or ‘odd’ jackets. Indeed, what differentiates an odd jacket from a suit jacket in the first place.

There are two factors: cloth and design. Both make the jacket more casual than its suit equivalent. The cloth can be casual either due to greater texture (cashmere, tweed, linen) or greater pattern. In the picture here, the lightweight flannel has more of a woolen finish than a smooth, worsted suit, but the informality is largely achieved through its strong pattern.

The second factor is design. Anything that breaks up the jacket – in the same way as the pattern – makes it more casual. This largely comes down to buttons and pockets. Patch pockets break up the visual impression of the jacket, as do buttons that contrast with the material, whether they are horn, metal or mother-of-pearl. It is for that reason that the traditional (now largely American) blue blazer always has gold buttons. Even if the cloth is fairly smooth, the buttons do enough.

Of course, the harder question is how to wear one. I’ve written several posts about styles of odd jackets and the best odd trousers to wear with them. If you haven’t read those already, they’re a good place to start. There are many permutations, however – if I ever get round to writing another book, it will likely be on such odd-jacket combinations.

In this example, ever-versatile charcoal trousers from Caliendo are a good balance to the Anderson & Sheppard DB jacket. The addition of a crewneck sweater does much to replace the absence of a necktie. The ready-made shirt from Phineas Cole is a lovely worn denim, but unfortunately a tad short in the collar for my neck. (Look out for a project for stonewashed bespoke shirts in a couple of weeks.)

The picture was taken recently near my office by the lovely Jose Cabral, author of O Alfaiate Lisboeta (The Lisbon Tailor). 

Notify of
Inline Feedbacks
View all comments

Enjoyed reading his article as I have a similar plaid patterned jacket but in a lighter brown ,almost cream, color .
With regards trousers I’ve defaulted with dark blues.
What trousers would you recommend ?

Also would you consider a v neck sweater with such a jacket or does a round neck generally work better with a jacket and no tie.?


In addition it would be good if you could educate us more on skin tone/colour and what colours to wear .
Being Indian I’ve noticed some colours (cream, light brown ….as in teh jacket mentioned earlier ) may not work too well.


great article! Would you please expand on your comment about the traditional blue blazer being largely American.


Is it the brass buttons that identify the wearer as American or just the fact that it’s a navy blazer,even if the buttons are black horn for example.
I wouldn’t be seen in a blue blazer with brass buttons personally,but I have one with black buttons that I wear regularly. So, does wearing a blue blazer,even with nice,understated buttons outside the United States identify the wearer as American?


Simon. What a jacket!!! Very brave! Keep up the good work.


Great insights, as always, into a very tricky area of men’s style. In today’s casual offices, a suit and tie is often inappropriate (unless you work in banking or law) and so odd jackets and trousers are a great way to look stylish without appearing too formal.

Would love to see a post on your favourite jacket and jeans combos. It’s a much derided look (largely because it’s so often done wrong, with a worsted grey suit jacket paired with stone wash jeans) but I think, when done properly, it’s a great way to dress up the modern business uniform of jeans and shirt.

Also, looking forward to your post on bespoke demin shirts – I’ve been trying to find a good denim shirt for ages (to channel my inner Ralph Lauren) but everything available OTR seems to be “Western Style” with snap pearl buttons and Western shoulders, which doesn’t really look right under a jacket.


Yes, absolutely – I like the use of a sweater to add extra colour in place of a tie. Always open to any other sources of inspiration though…


“There are two factors: cloth and design. Both make the jacket more casual than its suit equivalent. The cloth can be casual either due to greater texture (cashmere, tweed, linen) or greater pattern.”

You seem to be assuming that a suit is always more formal than a mismatched jacket and trousers combo. But a casual style can work very well in a suit – only of my favourite outfits is a donegal suit from Timothy Everest with patch pockets and a shooting patch on the shoulder. I wouldn’t wear it to a business meeting but it’s just the thing for a smart sunday lunch. And equally a mismatched jacket can work in a formal setting – as exemplified by a velvet dinner jacket with barathea trousers.

Kelly See

Hi Simon. I got myself a pair of bespoke John Lobb St. James last week. Got a pair of plain black cap toe with a slight soften square toe. Would you suggest any other style that would be more interesting? Do you have any experience with John Lobb St. James?


Hello Simon.
I cannot quite figure out the colour of that round neck. Is it black or dark navy? Could black fit the bill?

Very much enjoyed the post. Thank you.


Blazers / brass buttons.

I’ve often seen British gentleman of a greater vintage walking around the plusher parts of London with these and I think they look smart. I’m guessing they are retired military.

I personally like the look as a younger gentleman, and I think it can look very dapper if the blazer has silver or gunmetal buttons with a crisp white shirt and jeans and brogues or monkstraps. Not sure how ‘correct’ this would be, but to me it looks smart. Obviously it has to be fitted.

I don’t have one of these jackets yet, but I plan to add one this year after selecting the right tailor for it as the modern RTW options I do like never fit me.


Hi Simon. Thanks for a great post. I am really digging your worn denim shirt.. I know you said you will publish an article in a few weeks on this, but any quick tailor recommendation in the meantime? Thanks!


Hi Simon, when buying suit trousers I am roughly between a regular length and a long length. Is it better to purchase the regular and have them adjusted or purchase the long and have them adjsuted?


I find this with lots of trousers – 32″ a bit short but 34″ a bit long! Quite annoying.


Thanks Simon. What about the shirt D’Avino made for you? Would it achieve this effect after a few washes?


What is entailed in these specialist washes?
How much does it affect the lifespan or quality of the cloth. When buying from upscale retail outlets that wear cloth like this (such as RL) I never know how much damage it does to the fabric and if it therefore isn’t worth the investment?


Hi Simon,

Great post! I”m considering investing in a good quality distressed jean shirt in blue. What, in your view, would that work with? I paired it with a pair of navy slim fit Incotex chinos but the contrast seemed too great. Any ideas very much appreciated?


Aha! Many thanks, Simon.

John scott leith

I enjoy immensly permenent style , find the Anderson and Sheppard d b jacket to bulky for you lapels half inch to wide and jacket one inch to long , however good looking odd jacket ,as i was the tailor and designer for the Beatles at Apple Tailoring in the Kings road ,during the late 60s i know how difficult it is to get everything just right,