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.


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.)

No. 1 (explanation lower down)

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.

Jake: No.2, Alex: His own invention.

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

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I love this pic of Chad Park (B&Tailor):comment image. Having a vertical frame around shirt/tie but with more fabric than usual looks very pleasing.

What do you mean by rolling up shirt sleeves twice? Two rolls, so they sit mid-forearm rather than above the elbow?

Rob D

Chaps roll their sleeves up below the elbow, blokes above the elbow.


No 2, above, is perhaps best depicted by Prince Charles who always seems to have one hand the pocket of his DB jackets


Hello Simon,
Do you know who made the blazer in no.4 ?


Thanks Simon.
Of course how stupid of me not to recognise the great Valentino !
I will try harder next time.


Will you commission a Sciamat jacket at some stage? I appreciate it may not be your favorite style but their technical and stylistic pitch calls for a review, doesn’t it?


Some minefields and ten-foot bargepoles here. Whether one looks old-fashioned, contrived, stiff, or anachronistic depends on so many outside factors, most of which bear no relation to tailoring or the clothes themselves. Celebrities, for instance, get away with anything. Because people don’t just look at the clothes. They look at the wearer.

Ditto for executive jocks or the upper class. The confidence, good breeding, inherited money, and loadsamoney afford them a lot more style leeway than us mortals.

Then there’s haircuts and facial hair, and wrist accessories. Someone with a classic short-back-and-sides will look odd if they practise extreme iSprezzatura.

And let us not forget body shape. Tall can get away with most things. Tall and thin can get away with anything.

Finally, there’s circumstance and environment. A supermodel hanging on your elbow will get you into the most exclusive clubs known to man. She will also let you get away with breaking sartorial rules. Add champagne and perhaps a cigar, and you’ll look good in anything.

That’s a reason why sartorial brands trying to market their softer, relaxed sprezz outfits base their marketing on photoshoots of tousle-haire young men out on the town, and not young men in the boardroom. Ambience is nine tenths of the sartorial game. I won’t mention names, but Drake’s is one example.

Misshapen skint blokes belonging to the lower orders (I won’t mention names, but that would be me) find rules to be very helpful.


Class, confidence, ambience, good looks – 98%!

I enjoy the art direction of Drake’s shoots, and idealisation is always a part of style/fashion, but it could be a good creative challenge for them to show their products in realistic scenarios: waiting for the bus bleary-eyed, dealing with your toddler’s tantrums in the supermarket, taking out the trash, writing boring emails. (Or maybe not.)

Peter K

I don’t think i could pull off 1, 2, 4 or 5. I might try number 3 if I ever have a DB again. It relaxes the formality but keeps the nice lines and good fit of a DB.

Kev Fidler

I will have to go along with some of the more sceptical tones here. I am a bit non-plussed as to why you would go to the effort of wearing a jacket meant to be flattering and well fitted then deliberately pull it out of shape? I’ll go along with the hand in trouser pocket to give a slightly more relaxed, at ease look but some of the others could trespass into an affected look. (Putting your hands in jacket pockets to me either looks contrived, as when the hand is held fingers straight, thumb out like certain royals and senior politicians or pulls the cloth and cut right out of shape.) If you must give off a certain air why not just dress in something appropriate? Not having a go at anyone here, just thinking along the lines of the adage of dressing then forgetting about it.


1, 2 and 5 are fascinating – because I’ve never seen them written down, and have never considered that others might do them on purpose too. I’ve started wearing high-waisted trousers this summer (stoffa) and as such I’ve developed a number of new habits – which include a variation on 5.

I wanted to test out an old and unloved RTW DB linen jacket with them, probably my worst fitting, and so wore it undone to try and hide the poor fit around the waist. But to get it to look right I found that I naturally started putting my right hand in my trouser pocket – and using the arm to push the part of the jacket back behind towards the right (if that makes sense, its hard to explain without a diagram, but its sort of like Jake is doing in the photo below, but instead of staying on the hip the hand goes all the way to into the trouser pocket).

comment image

This keeps most of the jacket in a better place, while lifting part of it up a little and retaining some room for natural movement. This obviously has the effect of looking more relaxed, but also more interesting by virtue of being more unusual – and as a bonus getting to showing off those lovely trousers. Its also such a bizarre thing to do on purpose that it always looks totally accidental, even though its heavily considered. Now that jacket (wrongly) get more compliments than any other item I own – and I have noticed myself subconsciously doing my odd pocket manoeuvre regardless of what I’m wearing, having become a natural mannerism that I don’t even notice myself doing.

Everything seems to look that little better for it, and the gesture has become as much part of my personal style as any actual item of clothing. Glad to know I’m not the only one!


All three of your DBs look very nice. Are they by MD and Cifo twice?
These Cifo sleevehead ropes look very wide and fully filled with cotton rather than just a cigarette and empty space inside. Is it full indeed?
I notice your sleeves are rather ample at the arm level. Does it make you look more casual?


Correct me if I am wrong but you did not mention fastening the lower outside button rather than waist button. Why? This is very commonly employed and makes a DB more casual.

Fabrizio Gatti

Dear Simon. This is exactly the way I wear all my DB suits and odd jackets. To me, it’s all about not feeling awkward while walking down the street or in the office with whatever we have on, as long as we follow the only rule that matters: “good taste”. Anachronistic? You may be right… but I am also twice your age and, as a result, I started wearing DBs more than fifty years ago 🙂 Cheers, Fabrizio

Fabrizio Gatti

On the double-breasted jacket: a few thoughts.
1) You should not put your hands in the pockets, particularly for the sole purpose of feeling more comfortable wearing a certain garment.
2) If you don’t feel totally confident wearing a double-breasted jacket without resourcing to one or more of the tricks pictured above, don’t wear it. There is nothing wrong with that.
3) Yes, John Fitzgerald Kennedy used to put (occasionally and for a very brief moment) a hand on one of the lateral pockets of his single-breasted jackets (he never wore DB jackets after becoming president). So does Prince Charles with both, his DBs and SBs. For both gentlemen it is more like a sort of nervous tic (similar to biting the nails, which prince Charles -take a look at his hands- also seems to do, but never in public).
4) Prince Charles buttons the middle and the lowest button of his DBs, reminding us of their military origin. Many of us in other sites and most of the style experts have criticized him for this “horrendous” habit. The truth is that he is in a different planet in terms of style and he is definitely able to “pull it off” (mostly because of who he is). I certainly wouldn’t be able.
5) I sported my first DB when I was 18 years old. It was made by my father’s Milanese tailor (yes, I am still a fan of Milanese and British tailors; Neapolitans don’t thrill me at all). I told him once that I felt a bit self-conscious wearing it. Since he was an ex navy officer and loved wearing DBs in his civil life, this was his advice and it worked for me: “Don’t ever open it, don’t put your hands in the pocket just to feel confident, cool and smart. Walk down the street pretending to be an admiral wearing his blazer with metal buttons, that is straight and proud. A navy officer wearing his blazer wouldn’t be permitted to open his jacket’s buttons or put his hand in the pocket”. I repeat: it worked for me and it still works, even though I no longer pretend to be an admiral: wearing a DB has become second nature for me.
6) Sorry to say the following, but I don’t want to let anything in: none of the gentlemen in the above pictures other than you (in fact, in a couple of pictures you don’t have your hand in the pocket) are able to “pull the DB thing off”. They all seem to be self-conscious individuals trying hard to be smart and cool or to work some of what we in Italy call “sprezzatura”, that is “nonchalance”.
7) Dear Simon, I didn’t want to be disrespectful at all. On the contrary… I thank you for your very detailed and informative article and for the opportunity you give me, your follower and fan (and all your followers and fans) to express my opinions on this subject, which, in view of the fact that I am a DB guy, is very dear to me. I also would like to clarify what I previously stated about fastening the lower button: it has nothing to do with self-consciousness. It just elongates my figure since I am only 5’8”, even though sometimes I also, as most people do, fasten only the middle one: it depends on the mood.


Thanks Fabrizio, wonderfully put! (Yes yes, but better late than never)


Another I have noticed the Armoury guys doing is placing the tie between the jacket’s overlap. See Jake in picture 4, or Alan See

A little too contrived for me, but then I also used to use my tie loop and now never do…

Walter Sickinger

I have always thought a DB with a Tautz lapel, a horizontal gorge and somewhat rounded peaks, is much more attractive the the current trend of high gorges and sharp peaks which in some cases seem almost to reach the shoulders. Also a lower button stance does much to elongate the torso and eliminate the boxy look of some DB’s.


Hi Simon,
These are very helpful pieces of advice indeed. But I wonder whether a real game changer wouldn’t be a consistent effort by big Houses that have RTW lines to reintroduce the navy DB blazer or DB jacket in whatever color as a mainstay of their collections.
The DB blazer has lost its traditional territory for quite some time that first and foremost needs to be retaken. But such a task would require a collective and unflapable commitment, I’m afraid!

Gijsbertus van der Heijden

When I got my first DB, decades ago, some very ancient, sage and classically dressed gentlemen instructed that if one happened not to be a member of the armed forces or a brass band and nevertheless desired to wear a DB suit, that these were the rules:
1) When standing, cycling, jumping, laying in one’s coffin or walking one should always keep the lowest of the outer (functioning) buttons undone, whilst keeping buttoned all other outer and inner functioning buttons. (The only exception to this rule was when one was wearing a DB on which only the lowest of the outer buttons was functional. But such suits these gentlemen didn’t wear.)
2) When seated, however, one had to keep unbuttoned all functioning outer buttons whilst keeping the inner, jigger, button securely buttoned.

These were the old and established rules, they told me, simple rules, the middle way between maintaining a classic profile, important!, and being comfortable, which of course was less important. They could know, being born at the beginning of the twentieth century, or even slightly before that, into the upper and mostly well dressed classes.

Odd, by the way, given their humble and practical naval origin, that presently DB-suits are considered to be formal or even too formal. I suggest that people who are afraid of being too formal and old-fashioned when wearing DB jackets, instead of playing about with one or more of your five rules stop ordering such suits. Single breasted suits are perfectly acceptable too and a lot less fuzzy when it comes to the problematic of how to handle the buttons. (Apologies for my English; not my mother tongue.)

Nick Inkster

That is exactly how it should be worn, Gijsbertus.

The jigger is never undone; top buttoning always attached whilst standing but released whilst sitting.

Bottom button never attached (even if HRH does attach it).

So those are the rules, which of course are there to be broken.


Hi Nick,
“The jigger is never undone […]”. I’ve seen many among those considered as style icons wear their DBs COMPLETLY UNDONE! And with no hand in a pocket either …


Thank you.

Indeed, the shank of the jigger being a bit longer makes being seated with that button closed and all others undone a bit more comfortable. But at the same time, not too comfortable.

That is the essence: form, classic form, and conforming to these, and therefore being formal by definition, was de rigueur in the era of my stylish and classic ancestors, not comfort. I think this is the essential difference between these people and us: we value comfort, perhaps more than form. To them such an attitude would be anathema.

Nevertheless, even to them a measure of comfort was not unwelcome, hence, perhaps, the length of the jigger’s shank. One wonders if the tailors of their day and age knew more techniques to somehow combine formality with at least a bit of comfort. Techniques that perhaps have been lost since then.


I’d like to second Gijsbertus here.. just don’t wear or order a DB if you don’t feel 100% comfortable in it. Resist the iGent peer pressure in your head, you can! Given there are so few decent DBs available RTW you’ll most likely end up laying down serious money for something MTM or bespoke, only to try (too?) hard to make it look imperfect afterwards. Sounds a bit silly, really. If your budget has limits get a(nother) great SB instead and live in happily ever after.

Or proudly embrace the DB for all it may stand for (in the minds of others) and let it shine at its fullest. I can certainly relate to the hesitation of wearing a DB and have been down the i-absolutely-need!!-one-but-then-hardly-ever-wear-it road myself. But then again, every time I do get to wear mine, without thinking too much about how to make it look like I’d rather be wearing something else, I tend to get complimented for it. Just be aware of the occasion, as always.

Good series nevertheless, Simon.


They do look a bit like bankers…

Dan Ippolito

I agree with Oskar and Gijsbertus, especially with regard to the traditional navy DB blazer. One should wear it with panache and good posture, fully embracing its naval and military associations. The slouchy hipsters in the pictures above (not you Simon!) manage to look both ridiculous AND self-conscious in their attempts to wear a traditional garment with ironic nonchalance, a’ la David Letterman. But then again, that’s the whole problem with sprezz, isn’t it? It is fundamentally mendacious – an attempt to look as if you didn’t care about your appearance, while caring about it very much indeed.

I have been partial to the traditional DB blazer since the age of fifteen or so – I love its traditional aura and its masculine, chest-broadening effect. Who exactly decided that it is stodgy and makes one look like “your father or a fat cat banker”? The hipsters in their shrunken suits that make them look like ventriloquist’s dummies? Besides, what’s wrong with looking like your father? My father was one of the best dressed men I know, and I try to emulate him while at the same time cultivating my personal style.

I ask you, do these guys look like fat-cat bankers? and

In the final analysis, if you deface the beautiful, clean lines of an expensive bespoke garment in an attempt to look “hip” or out of fear of “what will others think” you are fundamentally disrespecting it and the craftsman who made it.

Dan Ippolito

If you say “Society as a whole decides that this is how a DB is viewed” then, in effect, we are saying this is attitude has become a RULE, and your article is about breaking the rules, isn’t i? 🙂

Secondly, I am a University professor and as such can wear pretty much what I want to the office, including occasionally a DB blazer, but I might concede that that type of garment is more suited to an evening out or an elegant daytime occasion than to the office. I would still insist, however, that wearing a DB blazer in an intentionally disheveled manner defeats the whole purpose of the garment.


Norms about what is appropriate or inappropriate to wear are, in fact, dictated by society, not by individuals. On the whole, these norms are created organically and evolve spontaneously, just like languages. That said, the individual idiosyncratic choices of high profile individuals (like presidents, royals, and celebrities) can exert a disproportionate influence. For instance, hats went by the wayside in America because the youthful JFK rarely chose to wear one. After JFK, it was difficult to wear one without looking like an old fogey. But all of this was happenstance; I don’t think JFK was intentionally trying to shape fashion trends.

That said, cultures can also vary tremendously on a local level. So for instance, DBs are commonplace (relatively speaking) in NYC but extremely unusual in Houston, so can get a very different reaction depending on where you wear one. Same goes for an office environment–bankers wear them commonly, doctors never wear them, and attorneys only wear them on occasion.


I love the formality of a DB suit, ideally a navy chalk stripe. It’s classic and stylish, not old-fashioned. DBs are the total opposite of the tight-fitting and short SB jackets that currently dominate menswear.

The 5″looks” are, as you suggest, contrived. 2 and 3 look crumpled, even slovenly. 4 and 5 are just narcissistic poseurs.

I’d rather look like a fat cat banker than an iGent sheep or a menswear “model” that few have heard of.


Irony abounds: the very attempt to codify nonchalance and the fact that the more we codify nonchalance the less convincing those codes. If you go to Pitti you’re fastidious—even if you’re not.

No. 3–5 look ridiculous.

I think solid DBs suits look great—love your Vergallos and MDs—but even I hold their fat cat association.


The more nonchalant the better. I’d be surprised if the Anglo-Italian gentleman ever fastened a jigger and doubtless stuff their pockets with keys, phone, wallet and all sorts more than just their hands – perhaps more functional after all. Valentino and George look like they can pull off any look they wish with style.


I think having a DB made up in a 6×1 configuration, exposing more of the shirt in the chest area, tends to give a much more relaxed and casual vibe. That being said, I find an unbuttoned DB jacket quite elegant in itself, looks great especially with tone on tone, say a blue DB jacket with a blue Friday polo

my two cents


I agree with your take on the dangers of DB: people tend to look either outdated or rakish. My office in D.C. has about 150 male attorneys and I’ve yet to see a DB. For that reason, I can’t really see getting a DB for work purposes, but I am thinking of getting one for going out. About once a month, I have a night out with the boys and my wife goes out with the girls. (The kids stay with my grandparents–a perfect arrangement!!!) The gents tend to gravitate to a bar followed by one of the many steakhouses in D.C. We all tend to dress very smartly for the event, which makes it a lot of fun.

Do you think a jacket would be a better move than a suit for a DB for this type of occasion? Also, I’m somewhat short (5’7) but have a pretty athletic build (relatively wide shoulders for my height and a 37 inch chest). What sort of buttons do you think would be the most flattering?

Don Ferrando

6: If you come to Germany do not put both of your hands in the trouser pockets. It is considered very ill manenred and of poor education equal to poking in your nose.


Same here in the Netherlands.


When greeting people? That makes sense as one should not greet people with a hand in pocket or do you mean at any time. I.e. standing alone somewhere?

Don Ferrando

Never ever!

Fabrizio Gatti

Yep. No hands in any pocket at all.


I cant decide on a double breasted dark grey pinstripe ( like the owner of Zaremba wears in that well known picture of him) or a double breasted chalkstripe.
Can you help?
what are your thoughts?


It all seems very laboured to me. If you really have to try so hard to make a double breasted jacket work, why bother? There are plenty of other options. Personally, I don’t believe you can dress down a double breasted jacket. It’s just too formal.


I was thinking about this very topic not 3 days ago: how to relax a DB. I read every comment. All of you guys are completely nuts. And I love you for it.

Fabrizio Gatti

I totally agree with you. And yes, our passion for dressing style makes us all nuts: my wife says it too.


Hi Simon – long time avid reader, first time poster. Really appreciate all the advice and feedback.

Not sure if this is the right medium / the right place, but was hoping to take your input on an idea I’ve had.

I’m thinking of having a brown tweed DB jacket made by A&S, possibly in the Harris Tweed 89202 from Holland & Sherry you had a jacket made in. Tweed and A&S cut seem like interesting ways to slightly dress down the DB, and tweed DB would really come in handy in the painfully cold climate I’m in (US midwest).
Having said that, I’m worried the outcome might look quite bulky, and that thick tweed wouldn’t be very compatible with a DB.

Many thanks again for your all your insights


Makes sense – many thanks Simon, for the insight and the quick turnaround. I do have a SB / 2 button in a similar tweed, but might revert back to a brown flannel

DB Hickox

I love DB suits (not just because my initials are DB either). All my suits are DB, and all but one of my sport coats are single. I think it largely comes down to fabric and cut on how you should wear a DB, especially with regards to the lower button. I have a grey glen check flannel from Brioni, very formal cut, high and wide button stance, and the pattern makes it a bit over the top, but if I don’t do up the bottom button, it looks very unfinished. Like I forgot to do up the bottom button. I tend to wear it with black double monks. It’s basically my winter power suit, and my posture supports that.

However, my summer DB is Neapolitan (Isaia) lower, narow buttons, EXTREMELY light weight material, soft shoulders, dark blue glen plaid (brown for the glen and white over check), if I do up the bottom button on that suit, well, let’s just say I can see why people say you never should! I only do if the wind is blowing it around too much, but undo it once indoors.

So there are two different styles, that if you ask me, demand being wore two different ways. And I can see how if you are only familiar with one or the other, you can see why there are two sides to the “bottom button” rule.

My stand alone DB is middle ground. It’s white linen, almost vintage Isaia. It’s ventless, full in the sleeves, wide and high buttons, and can be worn equally well with bottom button done or undone, I can even wear it with the jigger done, and only the lower outer done up with I really want to play fast and loose.

Point is, it dependson the cut and material if the suit, how you should wear it. A point I think is evidenced historically by vintage men’s ads from the DB hay day of the 30s, formal jackets TEND to be fully buttoned, while separates and lightweights tend to only be the upper. I feel as tho this rule came about in the later half of the last century, when a lot of things didn’t make sense styalistically.

I also tend to wear my DB overcoats either fully buttoned or full open.


I think if you’re going to do it just own it. the danger is in doing it but not really having the courage of your conviction leading to the jacket lying at the back of your closet, or worse going about your business feeling generally awkward. btw where is your jacket from in the top main picture Simon? looks snappy.


Hi, what are the views on surgeon / functional cuffs for navy and grey suits for the office. Is it too flashy or not even noticeable?