This is the latest in a nice series of posts called ‘The Rules and How to Break Them‘.

Like the other Guides we have put together recently, it now has its own homepage, here. 

You can navigate to that page by clicking on the ‘Style’ section of the navigation and selecting it from the drop-down. You can also see a full list of the pieces on the right-hand side of this post. I hope you find them useful.

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Rule 8: Always keep your double-breasted jacket done up

In this series, which started a few years ago on Permanent Style, we explain why a rule or convention exists in menswear, and then how to break it.

The two things are closely connected.

It’s usually only possible to break the rules well when you know why they are there, and therefore what you are giving up.

It is often said that a double-breasted jacket (a DB) should always be kept buttoned – in some versions, even when you’re sitting down.

Why is this? Well, primarily because a DB has cloth that overlaps at the front, and therefore when it is not done up, there is an excess of material at the front that can flap around.

Of course, any well-cut jacket looks best when buttoned (otherwise there would be no point having it well made and cut), but this is particularly true of a DB, given the overlap.

Does this also aply when seated? Well, the effect is less, but there is still rather a pool of cloth when the jacket is unbuttoned. You’d have to remain rather upright, but the jacket will look best done up, and perhaps you should start that way.

Personally, I keep it buttoned if I’m at a table in a meeting, but quickly unfasten it if sitting in a restaurant with friends.

Either way I wouldn’t worry about it too much when sitting down. (And this is, perhaps, one important effect of this series – to suggest when you should worry about something, and not.)

So, it’s pretty clear what’s being given up if a jacket is left unbuttoned: fit, line, and the avoidance of flapping cloth.

But you might still want to break the rule, and here’s why.

Lovely as a DB is (and it is – it can be so flattering and masculine), the style is always at risk of looking formal or old-fashioned.

Few people wear a DB today, after all, even in offices where a suit and tie is required every day.

Partly that’s because it’s hard to get a good one off the peg, but mostly it’s because of those two risks: of looking over-smart and anachronistic.

The suggestion might be that you look like your grandfather or a fat-cat banker, but the risks are significant either way.

The easiest way to avoid this and make a DB seem more relaxed in the way you wear it, is to disrupt its clean, sharp lines.

There are several ways guys do this:

1 Put at least one hand in a trouser pocket, pulling up that side of the jacket

2 Put at least one hand in a jacket pocket, pulling it slightly out of shape (and suggesting perhaps that the jacket is more functional than it appears)

3 Leave the jigger button inside undone, so the back flap is loose and that lapel no longer straight

4 Leave the outside waist button undone, but the jigger button fastened. Often requires a hand in trouser or jacket pocket to work

5 Leave the whole thing undone. Again, hands in trouser pockets (pulling those flaps back) or jacket pockets also helps

These methods can all sound a little contrived. And they often are, at the start.

But over time they become second nature, in the same way I still roll my shirt sleeves up twice because that’s how my father did it.

At some point I must have seen him roll his sleeves (at a young and impressionable age) and I’ve always done it that way since. Anything else feels odd.

You can often see the same habits with men that wear DBs a lot.

They start putting their hands in the pockets, and over time it becomes routine. I use my trouser pockets heavily anyway, but if I’m wearing a DB I will instinctively pull back the jacket cloth as I do so – per number 1.

I also do that if it’s a hot day and I want to have the jacket undone, therefore avoiding waist flapping. Others use the jacket pockets.

Personally I’ve always found number 3 a little mannered, but perhaps it wouldn’t be if I did it every day.

Rules exist for good reasons. But there are also sometimes good reasons on the other side.

Understanding them, weighing them up and acting accordingly is the key – rather than blindly following one or the other.

Never trust someone who baldly states a rule without explanation or qualification.

(I should add that the cut and structure of a DB can also contribute vastly to how casual it looks. But this post is about rules on how any DB should be worn.)

Photography: Top three of me, Jamie Ferguson; others in order, @kerloaz, @ThousandYardStyle, @HeinFienbrot