David: I very much enjoy your blog and find it to be a great source of inspiration in my desire to master the art of permanent style. I was hoping you could help me in the matter of choosing odd jackets. I am starting a new job where most people wear a jacket but no one wears a necktie. I will probably wear grey flannel trousers, beige chinos and a light-coloured shirt. But I am not sure what odd jackets to wear. I don’t currently own any. What would you recommend to me if I have only one, three or five odd jackets to use for work?

The first thing to ensure about an odd jacket is that it goes well with the trousers. They must not clash in their pattern and they must be of a similar formality. As both your suggested pairs of trousers are plain, pattern is not much of an issue. And as they are both relatively informal, the jackets should reflect this in their cloth.

So my first suggestion to you would be a jacket in a pale grey, with a heavy texture in the cloth and in a relatively informal wool. So not worsted, but flannel, tweed, camel hair or something similarly rough. The heavy texture could be a herringbone or a hound’s-tooth. (Like the one pictured – from J.Crew)

The reason I suggest this for your first jacket is that the pattern is not too bold or eye-catching – there is enough visual interest to distinguish it from the trousers, but it is not a loud tweed. It is also classic and simple without being uniform – a blazer would offer less personality in your one item.

Your second jacket should be a blazer, though. Navy blue, preferably in something heavier than standard worsted wool, and fitting immaculately. Too many Americans wear a blazer and chinos out of laziness. Neither is likely to fit well and the jacket will rarely be buttoned. To differentiate yourself, get a blazer that is slim-cut, perhaps with just one button. And don’t go for brass buttons – something different, either plain blue or a different metal; perhaps even a cream colour like the Italians.

Third for me would be a tweed. The colour is a question of personal taste, as is the size of the check, but make sure it is slim (again) and smart enough to look at home both in the country and the office. I have a Donegal one-button tweed from Kilgour, in mid-grey, that I would put in this category.

Fourth, something for the summer – a tan linen or cotton gabardine. Make sure the linen is heavy, and if you think tan would be too casual, switch to a navy or a grey.

The fifth jacket can be something more adventurous: a classic black stroller if you want to add formality, something in an unusual colour like mid-green if you want to add flair.

When building the collection, just bear in mind that you want a spread of weights for different seasons and a spread of formalities for different occasions.