A reader commented recently (or rather, berated me) for not keeping my jacket buttoned. 

I understand the feeling behind this, but I also want to emphasise that just because it usually looks better, it doesn’t mean you have to follow this rule slavishly. 

It sounded like a perfect candidate, in other words, for our ‘Rules and how to break them’ series, of which there are now 11 chapters

The argument that underlies this series is that rules are more like conventions – ways of behaving which exist for a reason. They don’t have to be followed, but it’s nice to understand the reasoning first, so you know what you’re giving up when you break them. 



OK first, why does it look better to keep your jacket buttoned?

Well, because everything about the way the jacket has been cut and made presumes that it is. The shape from the shoulder, onto the chest, through the suppressed waist and into the skirt, has all been carefully designed to make you look good, on the basis that the waist button is fastened.

That button serves as a fulcrum, from which the fronts flow downwards around the hips, and the lapels run upwards towards the shoulders, emphasising width at the top and slimness in the middle. 

The lapels also frame the shirt, or shirt and tie, reinforcing the V-shape of the chest. And they hide the often puffy shirt, creating an uninterrupted line from the waist down through long, straight legs. 

Once the jacket is unbuttoned, a lot of this falls away. The jacket flaps open; the carefully sculpted shape, particularly in the bottom half, is lost. 

Whatever you think of Tony Blair, the ex-Prime Minister (and please don’t tell me what you think), he knew this well. Blair would always button his suit jacket as soon as he got out of a car, even mastering the one-handed technique, with the other hand raised in a greeting to the press.

It made him look better, but it also conveyed a sense of authority. 



There are obvious arguments on the other side. 

When you sit down, obviously you undo a (single breasted) jacket. If you’re stuffed after a particularly generous client lunch, you undo it too.

If you’re boiling hot, at the end of a walk through the streets of steamy Hong Kong, there’s nothing wrong with unbuttoning your jacket. Other things, like not fainting on the side walk or simply appearing comfortable, are more important. 

In fact, comfort is key here. 

We all know that appearing fussy, constrained or uncomfortable are the biggest killers to looking good as a man. Elegance requires ease.

Therefore if buttoning your jacket, for whatever reason, makes you uncomfortable, it’s a good argument to not do so. Just bear in mind the points above about what you’re giving up, and button it again when you’re back in an air-conditioned office. Or have it let out so it’s easier to wear. 



The more controversial argument for keeping a jacket unbuttoned is that it looks more casual – more suited to soft tailoring in soft materials, worn with casual things. 

There is something in this. A Neapolitan jacket often looks better unbuttoned than an English one, with the latter’s hard, sharp edges hanging a little awkwardly. The typical canvas used stops it from having much flow.  

And it’s certainly true that the more casual the tailoring is in other ways – hairy tweed rather than worsted wool, sports jacket rather than suit – the more fitting it looks to sometimes leave the jacket open.

On the other hand, a Neapolitan jacket arguably needs that anchor at the waist more, given there’s less keeping it in place. And it will still always be more flattering on the wearer when it is buttoned.

This point is more a question of your priorities, I think. 



A better argument might be that an unbuttoned jacket is easier to wear with the most casual of trousers, such as jeans. 

It’s perfectly possible for a buttoned jacket to look good with denim. I’ve shown an example above, from an article back in 2018. (Although I have to say that today, I would wear rather higher-waisted jeans.)

However, it is much easier to do so if the jacket is open, more like a cardigan. And given your trousers have no straightness or sharpness any more, there’s a good chance that the shape of the jacket is less of a priority as well. 

The jacket-and-jeans look is one I know readers often pursue, but not always (to their mind) successfully. I’d suggest that it’s worth keeping the jacket unbuttoned, and ignoring that purist nagging at them in their head. 



There are lots of men out there, working in a suit in an office, who never do their jackets up unless they’re cold. 

To them, I’d say, make more of an effort. Button your jacket when you get up from your desk, and chances are you’ll look better for it. It will hide that incipient paunch if nothing else. 

But there are also a few men – more likely readers – who know you should always keep your jacket buttoned. Because that’s the point of a jacket, and why buy a good one if you’re not going to wear it to its best advantage?

To them, I’d say you’re right, but loosen up a bit. Style is about how you wear your clothes just as much as which ones you buy. That’s why the men you admire look great when they pop their collar against the wind. Being relaxed is just as important as lines, fulcrums and silhouettes.

Don’t be so buttoned up.


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Gary Mitchell

Pretty much agree with all of that… the only thing I would add is that when wearing a waistcoat I would rarely button the jacket because of something so simple as preferring the look of it unbuttoned.


You’ve just written the exact comment that I was going to write. With the caveat that opportunities to wear a three-piece have become sadly rare in these pandemic times.

Gary Mitchell

You made me think about that… I just reviewed some photos and seems every one where I am wearing a waistcoat (or cardigan) I have my jacket open. Mostly pre-pandemic I think but it is Africa and mostly too warm.

Alex McShane

I still wear three-piece suits twice a week at least, but I still operate from an office, and also choose to wear them. I only ever button the jacket if I am outside and its cold. Otherwise i let the waistcoat shine.


You say…
“Well, because everything about the way the jacket has been cut and made presumes that it is”…

Is it possible to have it cut so it assumes it will be worn unbuttoned ?
And what would you ‘give up’ as a result ?

Prince Florizel of Bohemia

I believe that a white tie tailcoat is example of a double-breasted jacket with is cut to be worn open. The “double-breastedness” is off course highly stylized, however, it is suggested by two row of buttons.


I’m a great fan of Neapolitan tailoring and have had quite a few jackets made by both Ciardi and Caliendo (both of whom I discovered via Permanent Style, I should add). Some years ago, when I commissioned my second jacket with Elia Caliendo, we had a discussion about the lower quarters and the curvature of the line below the second button to the bottom edge of the jacket. Elia said that the characteristics of this line reveal the hand of the cutter even more than the lapel (which gets more attention, of course). Interestingly, he said that the open quarters of Neapolitan jackets are specifically designed to make a jacket look as good open as when it is closed.


Isn’t that how morning coats are cut ?


” It will hide that incipient paunch if nothing else. ”

I feel so seen.


What are your thoughts on keeping a jacket buttoned even when seated? The late great supremely stylish and elegant Sir Roger Moore often did so on screen and in real life albeit dressed in beautiful bespoke blazers, sports jackets and suits from the late Doug Hayward. What are the rules re this? Also any thoughts re the quality of Doug Hayward’s tailoring? He seemed to dress many stylish and elegant famous men. Was his tailoring more along the softer Anderson and Sheppard/Steven Hitchcock approach than the military tailors?

Jeans Lauren

You can see Doug Haywards tailoring in one of James Sherwood’s books where it’s explained in some detail, I think it’s Bespoke Savile Row

Matt Spaiser

Hayward’s tailoring was soft but it wasn’t a drape cut. It was very trim. He didn’t use much or any shoulder padding—they feel just as thin as the lower from of the jacket. The jackets felt very light, almost like a Neapolitan jacket, but they still looked British in the proportions and in the shape of the lapels and pocket flaps. Hayward’s style was quite unique but it wasn’t particularly flashy. His personality is always the focus of those who speak of him, never the style of the clothes.


Are there any short videos on this one handed button technique? I think this would be very helpful for me at work…

Is the ‘other active threads’ right under the article new thing or just a website glitch? If it’s a new thing, it’s quite disruptive going from article to comments.


It’s a silhouette thing. The jacket buttoned up is a good one. But wearing the jacket unbuttoned and putting hands in the pockets is another. It’s different, and conveys different ideas. For instance, when describing Blair you used a word “authority”, which is a pretty good choice. It’s just that I don’t care to look like that – he does it because he’s a politician. I’m not. I’m just a guy who likes to wear tailored things because they look nice.

Prince Florizel of Bohemia

I’ve always thought the traditional reason behind keeping the jacket button was to hide one’s belly, especially in case the wearer has a noticeable belly. And this was the reason, why it was ok to wear an unbuttoned jacket with a waistcoat, because it keeps the belly covered or “dressed”, as shirt was considered underwear. This might be a dated view, but I thought this was the traditional reasoning. 

Peter K

Since tailoring can have military origins it may also come from rules around uniforms.

Jeans Lauren

Prince that sounds about right. I’d also add that the top button on a coat helps to keep the tie anchored in place if the wearer has followed the longer tie trend and doesn’t wear shirt jewellery


Interesting detail re sitting down. I was observing the other day that Nick Foulkes (in his cigar videos) assiduously maintains a buttoned jacket even when seated for long periods. I noted that this appeared unusually sharp and elegant compared to unbuttoned, but maybe to others would come across as stiff. I also wondered whether it was quite a good test of fit – Foulkes’ jackets’ shoulders and chest remain perfectly in place, where possibly lesser made garments would crumple and bunch? Posture a consideration too there of course.

Peter K

Don’t newsreaders often wear the jacket buttoned while seated as well? I would guess it’s intended to add an air of authority.

Jeans Lauren

Posture and cut counts for a lot whilst wearing anything seated. Be it a waistcoat, or the way a coat is worn, with a slouchy posture slack will be created in the lines of any garment and they will start to bow. However once a person returns to an upright position the lines should flatten out and look crisper.
This is one of those immutable elements that requires a good core strength to maintain..


Precisely, last Friday I had dinner in a three piece suit and by having the waistcoat buttoned you are forced into a more upright position, which I never have when sitting.


I think that a well-fitting buttoned jacket *ought to* look good on a seated wearer if he sits properly upright (important point). But it is certainly more comfortable and feels more natural to undo it when seated. Unless one is a news anchor, when keeping it buttoned is important because the seating position itself is not intended to be that of ease/comfort but that of a focused presenter.


I rarely button my jackets, largely because the buttoning point feels too high (I’m talking about ready to wear here). I hope my first ever bespoke suit by John Kent will resolve the issue!
I saw Patrick of Norton and Sons on the box the other night, he was wearing what looked to be beautiful bespoke suit, but it was unbuttoned and as a result seemed to lose all it’s visual impact.

Nigel C

I’m reminded of Marty Feldman in Mel Brooks’ ‘Young Frankenstein’, if anyone remembers that.
“Paunch? What paunch?”
Best wishes N

Michael Gordon

I thought it was a “hump”.


About 10 years ago I had the same unstructured beige jacket from Boggi Tommaso is wearing in the first picture. Unfortunatley it was lost somehow. Eventough in the meantime all my jackets are bespoke I miss this particular jacket for its nonchalance. It was stretchy (I know), lightweight and quite wrinkleresistant. You could even roll it. Perfect for summer evenings. Fabio Attanasio had the same. https://www.thebespokedudes.com/en/brands/368/white-cream

Has anybody an idea how to get a similiar fabric to make it up as a unstructured bespoke jacket? Is that even a good idea?


I like the unbuttoned look much better. A buttoned jacket looks uptight. If you need to be very formal why not wear a three piece but leave the jacket open?


Good post…nice points.
When I wear a crew neck sweater under a tailored jacket I invariably leave the jacket unbuttoned for a more relaxed look.Likewise,I always leave a casual jacket like a Valstarino with a sweater underneath, unbuttoned.


I really like this series of articles. We also should not forget, sometimes breaking rules leads to innovation. Otherwise, we might still wear powdered wigs, a full-skirted knee-length coat, breeches and a lot of gold ornamentation.


Fundamentally I agree with the premise of this article. However, may I say that the unbuttoned look should never occur with a db jacket, it simply looks awful.


I certainly am and will read it, thanks Simon.

A Borda

I personally don’t love absolute statements such as these. I think whether a DB looks good really depends on the context when it’s worn, as with most things when it comes to dressing.

As Simon knows, I’m a great lover of DBs and have many.

Would I walk into a board of directors meeting with my DB jacket unbuttoned? No.

Do I worry too much if I leave my DB jacket unbuttoned when I leave the office at the end of a long day on a warm spring or summer evening and walk home from work? No.

The context in my opinion determines whether leaving a DB open is appropriate and looks good.


Hi Simon.
I think this is the main point about the useness of a DB.
When you unbottoned the jacket, it loose all the shape. I can see that it is a way to add some sprezzatura or freshness to the entire look, but with a big risk off loking afected.
Walking arround with a doble brest unfastened, simply looks messy for me.
Obviously, once in a time may be fresh or descontractured. But may point is that it isnt so versatile to wearing ussually.
By other side, nothing is less elegant and more affected that being unconfortable.
The style and elegance never have to clash with the confort. i really think that is the main rule.


With regard to this part of the passage: “ And it’s certainly true that the more casual the tailoring is in other ways – hairy tweed rather than worsted wool, suit rather than sports jacket – the more fitting it looks to sometimes leave the jacket open,” is this saying a suit is more casual than a sports jacket, just as a hairy tweed is more casual than a worsted?

The article is excellent, and mirrors my experience as well. My wardrobe use to consist of entirely Neapolitan suits (that eventually became too small around the waist due to too much joie de vivre and not enough exercise), which I always wore unbuttoned. As I have moved to English drape courtesy of Steven Hitchcock, I find that the jackets hang wrong unbuttoned and look as if I forgot to button them as opposed to the Italian jackets looking more at ease with an open front. Kind of a reverse step to the rest of the world where I end up dressing more formally as time goes on as opposed to the opposite.


Sorry I was not more clear, I meant to say as well that it was due to Neapolitan v. English in my experience, not suit vs. jacket specifically.

John C

Thank you for that article; I enjoyed it. Like many of your articles, it helped me work out (i) what I feel strongly about – and why (whether it’s by agreeing with you or, occasionally, by articulating for myself why I disagree with you), (ii) what I can be convinced of, and (iii) what is just my style, for better or worse.

It was interesting that you thought open jackets and jeans go together. You’re probably right. But one of my first determined style choices (aged about 19) was to stop wearing jeans. The connotation for me wasn’t cowboys or workers or democratic freedoms, but my father at the weekend (I loved him, but knew I didn’t want to dress like him), and Jeremy Clarkson, and friends who didn’t know how they wanted to present themselves so bought whatever was being sold by Levi’s. (At that time, I had little cash, so it was simply a matter of switching denim for dark chinos – but at least they weren’t jeans and I’d made a choice.) This, surely, falls into (iii), but I’m stuck with it.

However, I’m pleased to know that one-handed buttoning is a technique. I hadn’t thought of it before. In fact, I’m worried that now I know it’s a skill I have I’ll be conscious of it and it’ll become an affectation, rather than something I just do, as a woman might smooth her skirt…


Of all the things to be *berated* for…?


If I can summarise this: “F*** it, if you know the rules and what you’re doing, do what you want. ”

No better message out there.


I have a theory. The reason why unbuttoned jackets have a reputation for not looking well is because so many jackets in general are too snug, too tight. Of course, they don’t look good buttoned up either. But because they are snug, their wearers are more prone to leaving them unbuttoned.

I think a jacket that fits well, on the other hand, looks good unbuttoned, if a casual air is what the wearer is going for. I don’t look at any of the pictures in this articule and thing “This is terrible!” On the contrary, they look fine, because your jackets fit you well.

An unbuttoned jacket also looks better when the wearer is in decent shape, weight-wise… but again, this is true for buttoned jackets as well, though maybe to a slightly lesser extent.

In short, if the jacket fits well, it will be fine unbuttoned.


The stipendiary magistrate who sat in the Hull Magistrates’ Court in the 1980s would never allow an advocate to address him whilst wearing an unbuttoned jacket unless said advocate was wearing a waistcoat.


Wow. What an asshole.


True, I probably didn’t need to write that. However, this is exactly what I was thinking. The person Thorn describes is the kind of guy who gatekeeps newcomers and writes snide coments on Ivy Style. But those people at least keep to the internet, he does it in real life.

Eric Twardzik

In the U.S we have the polar opposite in the form of Ohio representative Jim Jordan, who is notorious (among many other things) for never being photographed with his jacket on. It’s forever slumped on a chair or tossed under his arm or over his back. Enough so to seem like a deliberate (and not so complimentary) aesthetic choice.

Peter O

What do you expect from Jim Jordan whose adolescence and profession was about excelling as athlete and I think it’s important here to specify wrestler who achieved really top records and an
extraordinary career and coached young wrestlers for a living, and now is a main contestant in the center of extraordinary national political conflict?
Just as Jim Jordan was and is at the top of both wrestling and political arenas, so Simon Crompton is in the English speaking world an extraordinary sartorial coach who does not have time to learn wrestling as far as I know and would not be criticizes if he lost a wrestling match or two.

Rob Mac

Great post. What is your preference when wearing a necktie? I think it depends on the formality of the occasion, the button placement and how much of your necktie you want to display.
Rule # 10 is a pet peeve,especially when a suit is worn with cufflinks and a pocket square. If you’re are going that formal then put on a tie.
Pet peeve #2, suits or dress trousers worn with athletic footwear.

Peter O

Dear Simon, aside from buttons –

If you view yourself in the photo walking across the street – 1. your suit jacket is cut majestically large 2. your trousers seem quite narrow
3. what catches the eye first is the distance between shoe and trouser cuff, now backwards, the relation of enlarged suit jacket and reduced trouser seems unbalanced and your
figure becomes comical. Get my point?

Your suit jacket isn’t in the right proportion to trouser cut. The jacket is too big, the trousers too shrunken.

No offence intended.

99% of your dress otherwisd belongs to uppermost 1% of suaveness.

Jeans Lauren

Simon Peter has a point, but it’s mainly the trousers that aren’t doing you any favours. This could easily be changed by adding in an odd pair of full cut self supporting trousers. Please continue to take comfort in your nice coat.
I suppose you could also easily get another pair of full cut slacks cut in the same navy cloth from somewhere else if you wanted too? But very few men without a trained eye would ever notice, it’s really something only an enthusiast would grumble over..

Peter O

Dear Jeans Lauren,

Anytime I view Simon I realize he’s on an aesthetic level I’ll never achieve but always admire, and to my defense I admit I have abstracted from everything else (colour, etc.) except what maybe professionals might call something like OUTLINE of the WHOLE presentation, considering the 3-dimensional shape.

Peter O

OK – I’m too subjective and emotional. Instead of “comical” what about “out of proportion” – top-heavy?


Excellent article, Simon! All wonderful points and very well explained and illustrated why the jacket is best worn buttoned and what will be gained/lost by wearing it unbuttoned.
The rule is there not just for ‘propriety’ and ‘correctness’ (both less important today than in the past) but also because it simply looks better that way 99% of the time, making it the standard choice, i.e. a rule, from which to deviate at own risk.
The last point is particularly important – the key is to be comfortable and effortless. Maybe we can try to do the unbuttoned jacket look a bit of ‘sprezzatura’ too. Let’s not just mess up ties and collars, but the jackets too, no? 🙂
P. S. I noticed on Instagram you captioned Tomaso as being of S. Bemer. I may be a latecomer here, but isn’t he also of Vestrucci? Have the two merged? Has Tomaso left Vestrucci?


Oh wow I had no idea. I mean they are a match made in heaven, I was just totally oblivious to the fact 🙂 Thanks!


Actually, Bemer and Vestrucci were separate entities (albeit both florentine) until the other tomasso (no relation : ) took them over and merged them.
ciao caro to both tomassos?


I do agree that it looks better unbuttoned when worn with casual things. I have tried buttoning the jacket while wearing a t shirt under it and I simply can’t do it.


It may not merit the effort to write up, but a sub-point here is closing all buttons. I seldom do, but once in a while it makes sense especially – horror of horrors – on 3-button jackets where the lapel ends quite high up. It accentuates the line of the jacket – literally the vertical line down the middle – and this can sometimes be a nice thing. It also makes sense when it’s cold out!


Hi Simon, do you agree that as a rule dinner jackets should be worn unbottoned? Or does that depend on whether there is a waistcoat etc?


Hey Simon,

Who made the blue single breasted suit in the second picture? That is my ideal type of cut for an English suit.


It has to be mentioned that most „modern“ high street jackets are not designed to be buttoned, I think. Or at least they look better undone, because the ultra tight alternative is just too silly. And there would be even more of a collar gap etc. when you button those jackets.


I assumed because of a statement from the late Karl Lagerfeld, that jackets look better when they are not buttoned. So I thought he must know that this is made on purpose. But you might be right.
By the way: Is it fair to say that Hedi Slimane started this short- and tight-trend in his time at Dior?


I was never looking to him for guidance, I just assumed that he basically “admitted” in his statement that the consumers of this look (like himself, a Dior Homme consumer) should put up with the fact that their jackets are too tight to look good when buttoned. If that makes sense.


Bit of a weird, probably stupid question: if you’re wearing a coat over a jacket, keeping the coat buttoned, and you know you’re going to be sitting and then standing back up a lot (e.g. using public transport) would you keep the jacket unbuttoned? I normally would’ve kept it buttoned and put up with the slightly more uncomfortable feel, but with you saying about it not being good for an SB jacket I’m unsure.

Ryan Merc

Buttoning both (all) buttons, or just one? If one, which one–top or bottom?

Ryan Merc

Good stuff! I enjoyed this one.


The blue jacket in the photo with the Panama hat is rather nice, Simon. Is it a linen and wool mix and may I ask the provenance? BTW you used to tell us this in earlier articles, without us punters having to ask!


that orange shawl/scarf over the coat is pure science and elite outfit architecture


The cream jacket with green trousers outfit is splendid, I cannot stop looking at it.


You referred to ex-Prime Minister Tony Blair buttoning his suit jacket and conveying a sense of authority which I fully subscribe. The absolute counterexample is Donald Trump sporting his awfully too long ties and his jackets always unbuttoned and sending the same message as his wife Melania on her Zara field jacket: I really don`t care, do u?

S M Saleem Ali

In Pakistan ,suit wearers usually keep the jackets open and if somebody closes all the buttons ,he is made ridicule.


What do you do if you are playing an instrument in a band/orchestra?