Caliendo navy hopsack blazer and brown linen trousers

Four things contribute most to the formality of an outfit: shine, darkness, contrast and desaturation.

We see all four of them in formal outfits such as black tie. Dark black or midnight blue is contrasted against stark white. There is virtually no colour – perhaps just a dash in the handkerchief or boutonniere – and there is shine in the grosgrain silk, the shine of the shoes.

Navy is the more common starting point for formality in a lounge suit. When considering what to wear for our Tailoring Symposium last month, therefore, navy was the first thing on my mind.

It was a hot night in Florence, and a double-breasted jacket would be more formal than single. So my navy hopsack double-breasted jacket, from Elia Caliendo, fitted the bill.

Next, the trousers. Grey would have been the formal default (plain, lack of colour, enough contrast with jacket and shoes). But I was keen to try my silk/linen brown trousers from Panta Clothing. They are very light and the silk gives them a slight sheen, which suggests a touch of formality. I’d consider how to get enough contrast with the shoes (see recent post on Caraceni) later.

For shirt, tie and handkerchief, the default formal option would always be a white shirt, plain dark tie, and white hank. This achieves the desired elements of darkness, contrast and desaturation. This is why wearing a white shirt in the evening is, for some men, a useful rule of thumb; it usually makes any outfit more formal.

But the top half would have been dull if it was just plain navy and white. It might also have looked detached from the trousers. So I substituted the shirt for a pale grey. That retained the lack of colour, sacrificed a little of the contrast, and injected a touch of personality.

navy double breasted hopsack blazer caliendo

In looking at the top half, above, note how much more formal the bright-white handkerchief and silk navy tie make it. A silk with more texture (eg grenadine), or with less shine (eg wool or linen) would have been much less formal. Equally a handkerchief that provided less unbroken contrast.

The shoes are brown-suede Belgian loafers from Rubinacci. I know some people dislike the sockless look, but I like it and my God it’s cool. They also created just enough contrast between shoes and trousers, due to the textures of suede vs silk/linen, and the black bow and piping on the shoes.

Also good here would have been the suede and velvet slippers Gaziano & Girling are producing at the moment (from £380). They have soles and heels that are a touch thicker than normal cemented shoes, making them much more practical than other slippers (including, I admit, these Rubi ones).

Tie from Drake’s, shirt from Luca Avitabile. For those in New York, Luca and Luigi Solito will be there in September – the 16th to the 18th, at HMS International Fabrics (730 5th Ave, suite 502). Contact [email protected] and [email protected]

Rubinacci belgian suede slippers brown

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Ivor Tiddler

Lovely outfit, but please stop tying your ties in the Italian fashion!!



I really like the idea of such an article. It is something I am constantly thinking about. I find if you try to dress well you automatically look more formal to the uninitiated, so you need to tone down the formality by playing with the textures, fabrics and styles. I wear a lot of more casual fabrics, to not feel out of place on the office. Linen shirts, fresco suits, knitted, shantung or tussah ties, brown shoes etc etc.


is it a Four-In-Hand-Knot? How did you “tie” it? Looks very nice to me, but i believe it has something of an Ascot-Tie which is making it appear more formal than a “normal” Tie-Knot. So, pretty more suitable for formal event. I am planning to do so on Saturday.


Great outfit and I love the lapels.
However, could you tell us about the quality of the loafers from Rubinacci?
A local store are selling them now, and I was just wondering if they are really worth the price.


Thank you for your reply!
They seem really delicate and because of that they don’t look really durable.
However, are they any brands you would recommend me checking out?


Great combination. Brownish trousers are a little risky, because too brown = too dull, isn’t it? But then the sheen evokes grey and contrast in a subtle way.
Your words on the crossover between sartorial and modern might deserve an article (or a series…) on it’s own. You have mentioned it before. In a way things have already become so much dressed down to an extent that when someone dresses formally it can look very stunning. As you have demonstrated once in a while, e.g. with pictures of cutter Michael Browne.


I really like the outfit (though the loose fitting of the trousers is not my style). One of my favourites you have shown.

Now I am hesitating of going to Naples to have made a blazer like yours at Elia Caliendo or at Solito. There is a difference in style? The finishing is better at Elia, I imagine.



Nice ensemble and I love the jacket. However, you state that double breasted is more formal than single breasted (autocorrect is trying to change that to breastfed, hehe). I was under the impression that traditionally double breasted was considered more casual, or do you think that this has changed over time?


First time I read this and found the article quite abstract e.g. “Desaturation” (I think it’s the philosophical P from your PPE degree coming to the fore!).
But a very good topic nevertheless rather like some recent ones around colour coordination and assembling a look for the day.
I think your response to Ivor is an article in itself .
How does one look smart without feeling out of place and somehow guilty !?
If I wear a suit to work I’m questioned about my state of mind and intention by colleagues .
P.S. Personally I love the tie .


The phrase ‘dumbing down’ refers to lowering standards in TV or culture, etc, in order to appeal to more people. If we lower our standards of formal dress, we only become part of the problem. Many people want to dress up but they lack the confidence to stand apart from the pack.

I believe in dressing up or down only as the occasion itself requires. The slobbish, shapeless, cheaply-made garbage that many people wear nowadays will have no influence on how I dress. I refuse to give an inch to those people. Why? Because when you’re right, you’re right. I haven’t got time to explain why to the rest of them.


Well, then I’d dress informally but not scruffily. I don’t do flip flops and t-shirts. I’m not going to wear a dinner suit to a barbecue! Maybe I’d wear chinos with a nice shirt or l/weight knit and suede shoes. Informal, but not scruffy. God forbid!


Ive just been on the G&G website looking for the slippers at £380 that you talk of and cant see them…?

Nick Inkster

Swelled edge again! Well done. I like the coat but not the way the lapels sit open.


Another fine combo – little to quibble over here.

However, i still don’t like the no-socks MO. If one dons a tie, a DB and a trouser containing silk, i imagine you already decided to put style above comfort so you might as well wear some damn socks.

Whilst i understand Simon’s rationalisation for ‘informalising the formal’, if you must; i find it is often ( not always) an exercise in futility . In this day and age, wearing a jacket of any kind (and tie) automatically conveys being dressed-up. The nuances we all partake is still very much esoteric; the wider world still sees our jacket, tie, ‘dress shoes’ pochette etc

Case in point: i was telling my wife and her friends about how i prefer textured ties: wool/cashmere, linen and especially silk-knits. And how the silk knits in particular are different, playful, fun etc, she proceeded to laugh, and she told me deadpan ‘It is a nice tie but ties are not considered fun or playful’.

Ipso facto, you might as well go the full hog as the average Joe on the street would not really care about your knots or your tie arrangement.


I do fully accept that there is varying levels of formality in ties, that clearly a knit tie doesnt look as formal as a satin silk model, however these are small degrees of separation and I really struggle to ever consider a tie “casual”.

Unfortunately this is part of my problem, I have seen many and bought a few great looking shantung and wool knit ties but just never have an opportunity to wear them. They are too informal for business and dont go too well in my eyes with smooth worsted suits but there are no events I go to out of work, particularly daytime, where anyone at all is wearing a tie. I’m already in a minority wearing a jacket even if I am pairing it with jeans or chinos.


Smashing combos – the second one in particular and they would of course like it. Maybe i wasn’t articulate enough, she does endorse and like my style.

The salient point is it’d still be considered formal to Joe Bloggs on the street. Heck, some of my friends have difficulty distinguishing between an odd jacket and a suit.

In fact, i am convinced that suits /ties one day will be like wedding dresses for many: worn on your wedding day, and then kept in your closet forever for posterity.


As soon as they invent something with better material than wool, in a cut that flatters you more than a tailored suit and has more pockets in more useful places to carry your junk – I’ll be first in the queue to buy it!


Absolutely superb jacket – looks amazing. Have you done a separate post on this yet?

What’s up with those trousers thought? They look really wide and ill-fitting (especially from below the knee).

I agree with the comments on the tie – there is sprezza and then there is over affected – unfortunately this falls into the latter.


I quite like these trousers, Simon. They’re a bit different to what you usually wear. I think the wider leg suits the temperature and the more stiff drape of the silk/linen cloth. I see these as a less formal trouser but I like the unexpected aspect to the trousers being worn in this way (dressed up).

I certainly don’t like a bare ankle with a tie, but then you’re not exactly wearing a suit. It messes with my head a bit (conflicting formal/informal messages) but I do like the outfit!


Simon, very interesting illustration on how to approach such a topic: thanks for that. And the tone of the shirt is great. A couple of non convincing points though. I think that wearing the loafers demolishes the entite construction, lowering by several degree the formality. At this point why no tie for example? A secondary one: hopsack is quite a sporty fabric, actually often used in blazers. Again, it lowers the formality of the outfit and undermines the entire approach then. What is your view? Max


Great outfit Simon! Navy jacket with brown trousers is an underused colour combo but works really well here – I think the textures you’ve used are key to pulling them together.

I find loafers rather difficult to get right. They are a lifesaver in the summer worn sockless (sorry Incognito!) but they always feel a bit too dainty with looser fitting summer trousers (although Luca Rubinacci always seems to be able to pull it off.) Yours look great in the pic but I worry about all that loose fabric flapping around like a schoolboy’s trousers when you walk…


+1 on the request for more thoughts on “crossover dressing” (sounds far too similar to “cross-dressing…) I have no problem with standing out from the crowd (being a Brit in New York also gives you a lot of leeway) but, when you work in a “business casual” office, a tie feels a bit inappropriately formal (no matter how much shantung, tussah, knit or cashmere it contains)

David Craggs

Sorry Simon but I think this outfit is, for you, a very rare faux pas.
The top half is fine but the trousers just don’t work.
The contrast in cloths is just completely wrong.
In my opinion, a linen suit in the correct weight works because the two parts bed in for a louche look.
Alternatively linen trousers can work with a seersucker jacket or with a traditional blazer but in this instance it looks like you’ve paired a more formal jacket with trousers that are too casual.
Finally, you appear to be currently very fond of your browns and tobacco colours. I can understand this because when it works, it works well. In this instance I’m afraid it just doesn’t.


One other question (sorry for all the posts – on a long, boring flight!) would you ever wear a double breasted suit without a tie?

I’m assuming no due to the formality of a DB but I’ve seen a few pics of Ralph Lauren rocking the look. (Still not sold on the DB suit with rollneck sweater look that seems very popular among bloggers though…)


What is the material/weave of the shirt? In a hot weather I am sweating with just the shirt on:). Do you sweat in this outfit?


Hi Simon,
This is a very chic outfit!
Your notion of desaturation deserves a post, I’m afraid!


Wow, interesting to see the controversy this outfit has generated in the comments section… Getting like the DailyMail here!

As I saw the outfit in person, thought I’d add my tuppence worth: short version I thought it looked great.

As always, context is everything which the more conservative commenters may be a bit unaware of. This was shot at Pitti Uomo – and there is absolutely no point going to Pitti Uomo wearing a standard navy two piece suit with a notch lapel and a matching navy tie, as lovely as that can be when done right. You’d just look boring amidst all the dandies. So you gotta raise your game as the saying goes. Pitti is a time to let lose on your sartorial wishes / darkest desires and gauge the reaction. One of my tailors described it as playing in the dressing-up box and I have to say I think he is right.

But no, this is probably not an outfit you’d wear to the office in a conservative business environment – however I don’t think it was advocated as such?

Of course, any time you break a rule and start to get subjective in your interpretations, some will love it – others, not so much. Others still will clutch their pearls and need smelling salts to be revived.

About the trousers being lose fit, again, in the baking Florence heat, loose fit works really well and again, as always, photos rarely, if ever, tell the full story in relation to fit…


Sorry to pull you back to this post, Simon. Frankly, I find it really instructive in many respects. Even your comments – starting with your first reply – as well as many made by your readers are full of cues! Unexpectedly enough, I have, for instance, eventually realized that the after-6PM-black-shoes rule can be easely broken without any sense of guilt. And believe me, it’s kind of sartorial liberation!

Christian Aamodt

Dear Simon. A quick question from Norway: what do you mean by “desaturation”?

Tried to look it up in a dictionary, but no such luck.

Kind regards
Christian Aamodt

facebook_Tim De Rosen.10153020919771711

All above the waist is very fine, particularly the coat. However the trousers are truly dreadful and look like a pair of (very creased) pyjamas.

Hi Tim,
Frankly, what would be the point then to have silk / linien trousers, obviously to be worn in hot weather? I thought J’s comment above were enough to settle this matter once and for all. I can’t help but wonder what kind of trousers you may be wearing or considering stylish regardless of environment, social or natural. Are you sure you don’t need to overhaul them? Such a simple step might help you save a lot of money and above all smarten up your wardrobe.


No socks! Et tu, Brute?

P.S. Ignore Tim; seems nice, but dim.


I intuitively think that the outfit—which is of course amazing as is—can benefit from 1) a heavier shoe and perhaps a trimmer leg opening and 2) a slightly shorter jacket. Both are for reasons of balance, though in different aspects of the outfit. Why have you chosen the proportions that you have?


I’m late to the party, but I was curious (and maybe I’m just missing the whole point here), but why not a dark suit for a formal evening, perhaps in fresco for a hot, formal evening? Or was the goal to show that odd trousers and sport coat can be used for formal events as well?


I see. This post actually came in handy for me – I have an upcoming hot (Texas) formal evening (concert) and my suit recently ripped. I only have one suit, since my profession does not call for suits. As it’s a two button, notch lapel charcoal, it has filled in wonderfully on formal occasions, night outs, and the occasional professional event that calls for a suit. In the time between replacing, which takes consideration given my budget and hard to fit size, this post was very helpful to me.


Not a bad combo. The sockless loafer look is too far left field from the rest of the wardrobe. Quality tan laceups would have been a better choice.

Guy Graff

This outfit looks wonderful. I reside in the Hamptons and NYC and my look is interchangeable with this. Blue and brown are great, often have fuller cut trousers and don’t see the negative comments about baggy making sense. Having some linen and silk in the trousers gives them charecter and very summer look. Hot weather and no socks…………….makes sense and looks appropriate.

Go for it Simon!


Simon this post made me wonder — what’s your view on tan/khaki trousers (so not brown, and with a wool/linen fabric without the silk’s luster) with a navy blazer in the evening? Appropriate, or only advisable during the day?

Clifford Hall

Simon, I am thinking of having a blazer made for summer wear, warmer months south and west in the U.S. Would be using it for business meetings with mid grey pants (sometimes with a tie) classic Italian background look, but also with chino’s and jeans. Often combining, travelling for business in more formal towns with less formal environments like LA. Any advice on the type of construction, material and color please.

Thank you.


Clifford Hall

Simon, thank you for the thoughts much appreciated as ever.



Great combo! can you tell me which tie from drakes you are wearing. On their website they have 4 similar navy ones: -50oz Royal Twill Printed Silk Tie, -Solid Super Repp Woven Silk Tie or -Woven Fine Rib Repp Solid Silk Tie.
kind reagards


Cool! Evening wear that is neither a suit or a tux is a topic not many people are willing to touch on. I’d like to ask you about your thoughts on applying the same principes to smart casual and casual evenings – not necessary clothes worn for special events, but also the day-to-day versions. I know there aren’t any rules to obey, but it’s for the sake of getting the most out of our wardrobes 🙂 For me it looks as if white ocbd/t-shirt is a good starting point, maybe with dark polos or turtlenecks as a variation. Then, low contrast separates – either the tailored kind or casual. I feel like pairing M65 with chinos follows the same colour choice principles… But probably both in rather dark colors than light, so navy jacket/mid-grey trousers than same jacket, cream chino? Or in reverse, say, charcoal trousers and tobacco jacket. Brown seems to get a lot of flak for not being an “evening color” but I think the “no brown after 6” is just pretty much about it not being a “city” color – dark, muted, cold browns look fine to me, up there with navy and charcoal. Black seems quite constricting when it comes to pairing, but it’s a classic. And then there’s the shine. Well, in more casual outfits it looks to me it could be the one thing to pass on, as shiny things could be hard to pair. A leather jacket or calfskin shoes would be probably fine, as long as it’s not too shiny. Although I’m wondering about a velvet jacket. Technically it could be worn as a evening sport jacket with grey/charcoal/brown flannels, especially in casual color like burgundy or dark green. Would it work with textured, matte tie like wool or cashmere? Or maybe dressed down even further. What would you say about all this?


Okay, I’ll try to turn this into more coherent questions. All of those are more about casual/smart casual situations, so suit is sadly out of question:
-Which colours would you choose for everyday eveningwear apart from the classic navy/white/black/charcoal? Is dark brown considered unsuitable because of how it interacts with artificial light, or is it just a relict of the whole “no brown in town” mindset?
-Are jackets or trousers in cream, tan or light grey okay for evening, or should I aim for lower contrast between jacket and trousers?
-Velvet jacket: Can it be turned into smart casual eveningwear, maybe with flannels, corduroys and textured matte ties?


Simon how do you find rubi Belgium’s compared to originals or Badoin? Or are they much of a muchness?


Great tie!