Dressing well is as much about propriety as it is about style, quality or personality. 

This is particularly true at work, where there are often prescriptions, or at least expectations, about professionalism and clothing.

I have often talked over the years about sliding scales of formality – about how formal certain shoe styles are compared to each other, or ties, shirts etc. In this post, I wanted to set out a sliding scale for whole outfits. 

In the ensembles below, I have changed one thing each time in order to make it more formal. So we start with something very casual, and with each new piece, become gradually smarter.

The different combinations are suitable to different work environments – or to different occasions. One for a normal work day; another for casual Friday; perhaps a last for the weekend.   

With each swap, the propriety changes. The same outfit with a shirt rather than a T-shirt, or jacket rather than knitwear, transforms when and where it can be worn. Small changes make a big difference. 

1. Ultra casual 

how to dress casually smart casualCommon Projects trainers

We start with the most casual combination:

These are all things that I have written about in the past on Permanent Style (at those links above) but I don’t think readers have ever seen me in such a casual combination. It’s what I often wear at home.

2. Add a shirt

how to dress creative button down bespoke shirt and shawl collar sweater

Adding a shirt immediately and obviously takes the outfit up a notch in formality. (From Luca Avitabile, chambray button-down.) 

Given the slight dressiness added by the shawl collar around the neck, and the sparkling-white Common Projects, this is an outfit I can see friends in creative industries wearing. When everyone else is in T-shirts and jeans, this is not too smart yet clearly implies extra style and presence.

3. Swap trainers for shoes

how to dress advertising gaziano and girling bespoke loafer

These first three elements – shirt, shoes and trousers – could have been swapped in any order. Flannels would have been an interesting look with the trainers, and these slip-ons could easily have come afterwards. 

But I feel these are the steps most men are likely to dress up in, particularly given the popularity of jeans. The bespoke hatchgrain slip-ons from Gaziano & Girling work with denim because of their colour (mid-brown), their style (loafer) and to a certain extent their casual texture. 

4. Flannels instead of jeans

how to dress creative agency how to dress cartier tank watch

Swapping jeans for flannels (bespoke, Anderson & Sheppard) is perhaps the biggest change in this step-by-step process. Jeans will never be appropriate in many offices, but once you’re in a shirt and trousers, this could even be worn in a law firm on a casual day.

Certainly, when men tell me they don’t know what to wear once they get rid of a suit, I would point them in the direction of this outfit and the next one: clearly smart, clearly well put together, but with none of the formality of a traditional, worsted suit.

5. Replace knitwear with jacket

how to dress at a hedge funds how to dress handkerchief

The sports-jacket-and-odd-trouser outfit is perhaps the office attire of the future. It’s certainly something that could save tailoring as more and more people abandon the suit. 

This combination is the simplest, easiest and most classic: navy jacket (bespoke, Solito), grey flannel trousers and a blue button-down shirt. The handkerchief will be too dandyish for many offices, but even if you remove it, you’re a hell of a lot more interesting than the guy in a suit and no tie. And this can be livened up with knitwear etc more easily too. 

6. A tie: the finishing touch

how to dress for a meeting how to dress with tie and handkerchief

A brown knitted-silk tie finishes off the outfit. Ties that are more casual – knits, wools, wovens – are easiest to wear with sports jackets, and a knitted silk sits bang in the middle of that range. A black knit-silk and darker brown shoes would be a step more formal. 

With that finishing touch, we’ve run the gamut from slouch to sartorial; with every stage in between. And again, if you remove the handkerchief this wouldn’t be too dandyish for many offices. 

So which would you wear, and when?

how to dress for any office

Images: Jamie Ferguson @jkf_man

Shot at the Anderson & Sheppard haberdashery, Clifford Street, London

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Brilliant. These are the posts I love the most – very accessible for all. Thank you!


Sadly I have to wear a formal suit everyday!

Usually somewhere in the neighborhood of #6 with a necktie (I enjoy these), and sometimes even suit (double breasted and a flannel three-piece during the colder months). None of this is required of course (I teach at a large university), but I enjoy dressing reasonably well, and it helps put me in the right frame of mind. And who knows? A few more students might be a bit more inclooned to take what I tell them seriously. Maybe.

Best Regards,

Heinz-Ulrich von B.

Dan Ippolito

I, too, am a university professor like Heinz-Ulrich von B. The sport-jacket and odd-trouser combination is my everyday outfit, even though less than half of the male faculty abide by it. I try to live by the “look good, feel good” motto, however, and a few (very few) of my students have started expressing an interest in wearing something other than jeans, t-shirts and cargo pants. And yes, I ALWAYS wear a tie.


Great post, Simon!
This post is very good for forwarding to friends, which are not yet hooked up by style awareness.


Love it! Thanks. I basically wear each of these outfits from monday to sunday.

Outfit 1: Sundays spent at home, otherwise Outfit 2
Outfit 2: Sathurdays on the market
Outfit 3: Casualfriday maybe swapped with a sportcoat
Outfit 5+6: Normal days at the office. Tie deppendig on mood and maybe what kind of client I’ll see that day.



Adam Jones

great article. Did nearly fall of my chair a bit seeing you in a t-shirt however.

It is surprising how many people believe that to make your work attire more casual you just put a full suit on, formal shoes and remove your tie!

A few more posts like this showing casual outfits would always be welcome, not just for the workplace. Pubs, Restaurants, Holidays etc.



I’d love to see casual outfits for summer time also, and for times when inclement weather in the British Isles forces one to wear outerwear while being too warm for knitwear underneath.


Sadly I don’t get to wear a formal suit everyday.


Most excellent. Please oh please Simon might you do an article on heat at home and on holiday? It’s starting to get to that time when things are thawing in parts of Europe and we need to be prepared !
Is it possible to wear shorts and shoes? Socks? Good materials, how to cope with sweat and sun? So many questions!


Sadly the standard of dress in my office is so low that pretty much anything which isn’t a shiny black / grey / navy suit from Marks & Spencer, or an open-neck shirt with a grey / navy jumper worn over the top is likely to stick out like a sore thumb.


In my office a navy jumper and open-necked shirt stick out as over-dressed because the norm is t-shirts, jeans, and trainers. The summer is worse – 3/4 length trousers, flipflops…
It’s a software company.


There are a few of us in the office who dress at the outfit 2 and 3 levels and I often hit 4 (then again I’m a director). Your outfit number 1 is way above the office standard in terms of quality. Shoes seem to be a particular problem for a lot of men.


Hi Simon,
Apologies for going off-topic here – just wondering what your experience of the green loden SB coat has been? Does the colour really work with a suit?


Love this post. I get the point that with many of your outfit posts you’re trying to “push the limits” of combinations but it’s really helpful to see some more classic outfits showing how a few basic items can be combined in different ways. I guess the fact that many of these items work across outfits of different levels of formality shows why they’re classics. The pale blue BD shirt seems to be notably versatile, spanning the range from #2-6.


Does Luca make your short sleeve polos, too, or do you wear OB short sleeve polos?

Alex H.

I’m an attorney for a law firm in Baltimore, and I’ve settled on the sport-jacket and odd-trouser combination at this juncture. More often than not, I also wear a tie. But, I distinctly remember the managing partner coming by my office to welcome me during my first week and he remarked on the fact that I was “still” wearing a tie. With but a few words, he had indicated the level of formality the office typically abides by. I do not believe I agreed considering that we are lawyers….


Lovely jacket Simon. What cloth is it made of please? I’m hoping to get my first bespoke suit for my wedding this year and have already scheduled an appointment with Solito in April. It’s a winter wedding so was hoping to go with something like a navy flannel (my preference was grey but I am under instructions that grey might clash). Would that work with Neapolitan tailoring in your opinion or would it be too much of a contradiction? Are there any other cloths you’re recommend for a winter suit? Thanks


Thanks. Clash perhaps wasn’t the right word but my wife to be has suggested that navy would probably look better next to her white dress. Best to follow instructions!


Fantastic article Simon! It’s amazing to see how each alteration kicks it up a notch. Also nice to see you in some more casual outfits. Would love to read more about how you incorporate sartorial clothing into your weekend attire.


Nice series, very real-life. What’s your take on contrasting vs. matching socks, and their roles in the spectrum shown here? You went for blue with jeans and grey with flannels. Do you ever go for purple (green, burgundy, pink, … ), and when? Thanks.


Hi Simon, great piece. The thing that struck me most is the comment that a simple white hank might be too “dandyish” for many/most workplaces. Is the implied suggestion that gents should/might discard this aspect of the outfit in some offices for fear of alienating themselves or creating the wrong impression? I certainly hope not!


Excellent reply!


Anyone know where one might source a bespoke knitted tie? My body is too long to make do with OTR.


Could try a bespoke grenadine from here:




thanks both…


This is one of my favourite posts and will no doubt be referring to it in the future for inspiration. 4,5 and 6 will be fine where I work and tried a similar look to 6 about two weeks ago (but without the square and with a cashmere tie from Drakes). Loved it but ended up getting asked if I made the tie out of tracksuit bottoms. Sigh.

Jose Torres

Such a beautiful jacket, thinking it’s the cashmere Solito jacket you wore in your scarf tutorial video. But I noticed a lot of your sports jackets fit a certain way, do you like them cut slimmer than your suits? Compared to your chest and waist measurements how much extra room do you prefer for your sports jackets to be cut with? Thanks Simon!

Greg Coleman

More of these please! I think they are of practical interest to most readers – even those without the budget to invest in some of the other pieces you have profiled.
I particularly like the final photo which clearly demonstrates that (unless a formal suit is required) you have the basis for a very versatile “capsule wardrobe” here. Enjoy NY. Kind regards – Greg


How the heck do you do that? Very stylish no matter what the occasion. I’ll have to keep signing in to keep up.

Thank you!


what is it about Sunspel t-shirts that you like? I’ve tried a few and found the cut uber strange, especially around the armpit area. JS is better, although nothing special when it comes to the material itself (this goes across the whole range of garments from JS in all honesty).

Not crazy about loafers with jeans, especially when the loafers are based on a longish last like on the photos, then again I generally dislike non-laced shoes, so that might affecting my judgment.

As for office areas, try the above in an engineering office (heavy industries, not software).

One last thing, is keeping the second button on a shirt unbuttoned a British thing? never seen so many men doing this, apart from perhaps warmer countries like Spain or Italy (and it’s not a majority of men anyway from what I’ve seen so far).


Matt S

I never unbutton the second button in an office, no matter how hot it gets in my New York office in winter! It just seems wrong in a business context to show chest, particularly chest hair.


Would you ever go with jeans and the sports jackets? Perhaps it would be 3A


Not convinced those loafers go with the jeans. They seem too formal for jeans. Perhaps suede loafers would have been better?

Adam Jones

looking at those loafers I think it would be great to have an update on some of your bespoke items on how they are ageing. I was in 2 minds about the colour of these loafers in previous posts but you can see they are developing wonderfully. So much I am thinking a hatch loafer could be my next shoe.. because I actually think they go really well with the jeans.


Excellent post Simon. I’ve always been a fan of these “guide” format posts, and it is always interesting to see how others work more formal pieces into casual ensembles.


I am a solicitor near Lincolns Inn London so its a suit and tie from choice Monday to Thursday. Outfit 6 for compulsory (shudder) casual Friday (unless in court) and Saturdays (no pocket square too ‘look at me’ for me ever to feel comfortable wearing one). Outfit 3 or 4 for Sundays with moleskins rather than jeans


Hi Simon,

great post. What’s your view on button-down-collar shirts with ties? Clearly, you approve in this post. Generally, in a business context I hate to see a tie and button-down shirt (a button down shirts I associate with more casual looks). As a rule I’ve never combined the two but admit it does look great in your post (I have a very similar-looking Emmett shirt and brown square end knitted tie again from Emmett). Many thanks, Rich.


I really like the proportions and roll of that shirt collar. It’s something that seems to be near impossible to find of R2W button downs in England, with most Jermyn shirt-makers seemingly favouring mean, shrunken little collars that produce no roll and can’t be worn properly with a tie. Can you recommend any UK-based retailers that offer Ivy-style OCBDs with a decent unlined collar? I’ve been looking at Drakes but it’s hard to gauge the quality of their shirts from the pictures on their website. Otherwise I might consider a US-based retailer if you can recommend one.

nick inkster

If you want the real deal on OCBD with the button down, try Mercer in the US.


What an informative post. Thanks, Simon.

A question about the jeans and sweater combination: how much contrast is there between the color of the jeans and the color of the sweater in real life? I have a similar navy shawl collar sweater (albeit not a cardigan) and when I wear it with jeans I sometimes feel like I’m wearing too much blue. Perhaps leaving your cardigan open allows a glimpse of your contrasting shirt to break things up?


Ultra-casual (according to PS) is how I come into the office now most of the time just out of spite, although I tend to add some Edward Green’s. Most coworkers (->law) are suit-only, although said suits appear to be made from the same material used for vinyl but spun into some ungodly thread. Also they colormatch ties and hanks. Also they tie their ties with windsor-knots, an especially disgusting misbehaviour and a pet-peeve of mine. I think as a next step I will get a full beard.

Yussef Robinson

How do you get creases to hold in your flannels? Even after pressing my VBC flannels lose their crease after about two wears.


What kind of socks (brand and material) are you wearing with your jeans and your flannels?


Those loafers really do look dressy.


Hi Simon – What is the leg opening of your jeans? I find that most of my jeans look a bit off with common projects because the leg opening and the sleekness of the shoe are out of proportion.

Also, what material is that Solito jacket?

john c

I’m not sure about the trainers. Very difficult to pull off for any man over the age of 25, they need to be absolutely pristine white and spotless. I’d be tempted to go for a pair of tods or a suede chukka. I guess that’s what makes a market! Love the patina on the G&Gs. John


I sort of agree on those trainers; I’m sure yours are nothing short of superlative in every aspect, but I’ve just seen some on a market that aren’t visually different for £5.99!
That’s a great look though, and scrolling down this post was an absolute joy.


Hi Simon

What’s your view on tasseled loafers with jeans and chinos? I’ve always thought the tasseled loafer better suited to more formal trousers.


My office is quite casual but I wear variations on number 6 most days. I wear a suit maybe once a week. Just often enough that I no longer get asked if I am going to job interview.

Numbers 4 and 5 for casual Friday.

Does the formality change in the summer for you Simon? It certainly does in my office.

John Vesey

As always you have terrific articles dealing with men’s style. I was sorry that you didn’t mention socks. When a man sits cross legged, his shoes and socks are prominent to those viewing. In your photos, your socks were changed each time you varied your pants.


Hello Simon, great article! My one question is regarding shoes – would a double monk shoe fit to the latter two styles (with the jacket)? Im am yet to fully understand, where double monks stand in terms of formality.


Best, Justin


Thank you, Simon, for the guidance! Mine are in dark brown with a slight polish, so I guess it might work, but I’ll better try in in front of a mirror at first. Just one follow up question, do you see monk strap shoes as a versatile style of shoe or quite the opposite? (the question is based on the fact, that I haven’t seen you wearing this kind of shoes on the posts)

As always, much appreciated!

Best, Justin


Justin, FWIW I find double monks very versatile as a nice middle ground that can be worn with flannels, chinos or jeans – I think of them in a similar way to chukkas. Probably a bit too casual for a suit (except maybe a Neapolitan style) but good with most other options.


On the note of trouser crease where do you stand with trouser presses?


I was always curious if the continuous pressure and heat could damage any fabrics?


Great post Simon, top 10 for me for sure, hope to bump into you in March in A&S!


You very often feature fantastically high quality brands, and I’ve thoroughly enjoyed some of these brands (especially albam), but they do tend to be towards the pricier side. With this in mind, what cheaper brands would you recommend? I’d especially love to find some wool trousers (~£100), Knitwear (~£150), and socks(~£10).


Hi Gus,

Simon has reviewed Viccel, a sock brand, favourably. Their socks fall into you suggested price range.

I recently ordered some socks from them and am happy with them.

For knitwear you might try Ralph Lauren. Trousers, maybe Howard Yount (a US brand). The trousers would be an online buy which might be tricky for getting the right fit.


I saw Viccel on this site as well. I think I’ll give them a try. Howard Yount looks Fantastic! They provide detailed measurements on their website so I’ll compare those with a well fitting pair I already have. Do have experiences with Yount’s shirts or knitwear? Also, when you say Ralph Lauren, which Ralph Lauren Brand do you mean? I had a nasty experience with Polo’s quality when I was younger and haven’t tried a RL product since.


I’m Canadian and due to our horrible current exchange rate haven’t tried Howard Yount yet. They get very favourable reviews as far as I know.

I was thinking Polo Ralph Lauren as it is in your suggested price range. Ralph Lauren Black Label is better quality but you might need a sale to find it in your range.

TM Lewin or Charles Tyrwhitt might be another decent source for knitwear.

I’ve also looked Woolovers, which are very well priced but seem to be rather generously sized and I suspect they wouldn’t fit my slender frame very well.


I don’t know if you revisit the comments Gus but eBay can be a good source of knitwear. I purchased a new navy knit waistcoat there at a very good price.

And John Smedley operates an online outlet with very good prices on really nice knitwear. It often features some rather odd (to my eyes) colours and larger sizes but I am watching it patiently for things I would buy.


Hello Simon,
On the Solito jacket – what colour are the buttons?


Informative post. Always a pleasure reading your blog, gives me plenty to think about.



What’s your view on navy brushed flannel trousers as a standalone pair of trousers? Ie not part of a suit. Could they be worn in place of the grey flannel trousers? Obviously, the other items would have to be of a different colour.


Love the Solito jacket. Just curious, do you think navy fresco would be an acceptable material for an odd jacket? Or would it look too much like an orphaned suit jacket? I love the way the cashmere looks but it gets so hot in the summer here in NYC and I really need something a bit smarter than the tan cotton staple.


Simon have you ever played with, or thought about, raw silk for a jacket?


Brilliant article Simon and so interesting.
I do believe that jeans and indeed T-shirts are a no-go for anyone over 25. They are the demise of civilized society regardless of their cost and who made them and personally, i believe point towards a lazy choice.
I would kill for those Gaziano shoes, love the light grey flannels, dislike the shirt when buttoned up with a tie (button down and tie again a no-no for me as it look sloppy American) and, although i like and even own several knitted silk ties, i have yet to see an attractive knot on any of them. They just do not seem to work (any tips on this although i see in your images, even you seem to struggle). And lastly, i think the knit gauge on the shawl jumper is great, chunky but not overly so. I purchased mine from the now closed cashmere shop in Burlington Acvade (cannot recall the name) in camelhair and regret it. Too thick and bulky and actually too warm for London. When that comes out the central heating goes off! Again blue is a great choice – stay away from camel as i find it not versatile enough

john c

Yes! I completely agree with knitted ties. I own a few, they’re great in theory but I’ve never seen them carried off in practise. Even on the Viola Milano website- and those lads can carry things off. As for the outfits in the article, the individual articles seem nice enough, but it’s all a bit dull. You might as well wear a suit. In the first with the jean t shirt etc. Everything’s blue and grey, there’s no pop or flair, why not try some cords to add a bit of textural variation- or something from the other side of the colour wheel- a burnt orange v neck under the cardigan? Same goes for the other outfits- everything is a neutral shade and the same texture. Nice clothes individually but crying out for some imagination concerning variation or colour somewhere.


Very enjoyable post. Would love to see a summer version for the warmer weather.


I’d second that idea Simon. From the amount of comment generated this must be one of your most popular posts.


Fantastic Post! Thank you Simon.
Unfortunately I work in the financial sector and I wear a suit everyday!


Great item (thanks) but what interested me were the large number of replies and what most people are saying they wear at work. In my industry (software) the norm is about minus 3 on your scale – anybody with clean trainers or a t-shirt that does not have a Star Wars character is unusual! I tend to go with number 3 but it would be impossible to go beyond number 4.


Great article idea Simon, 101 comments and counting! I like the path you have taken re. the neutral colours – pop colour can be individualised and added thereafter. A little feedback if you’ll allow; the seated pose (Ian Fleming called this the Clubman pose) isn’t helpful to the image. Understand that you wanted consistency but the raised leg obfuscates the shirt/tie area. With a little change the pose could have been retained but shot from an angle slightly to the side (camera lhs would have been better). Can I gently urge you to consider the range of poses and camera positions frequently used in men’s fashion to fully complement the garments featured. https://www.pinterest.com/explore/male-models-poses/


Great post Simon.

What kind of outerwear would you recommend with look 4, perhaps a harrington or field jacket? I always find it hard to match casual non-tailored jackets with proper trousers so I usually opt for chinos instead.


Hi Simon

I’ve a pair of black chinos (impulse buy!) that I’m trying to pair with a suitable pair of shoes. I’m thinking a pair of black penny loafers. Ideally, I’d have gone with a suede pair or a pebble grain variant. However, these are not readily available. I could them MTO but I’d rather explore other options.Would you say I could get away with a standard calf skin pair? Or perhaps a cordovan pair?



Thanks for the advice. Was hoping the smooth calf would be OK. It was a case of I liked the fit in one colour and then bought several pairs in other colours…….including black. However, once I got to thinking about how to wear the black ones, I realised it was a bit of a silly buy! Still, I’m going to wear them with a John smedley charcoal long sleeve polo, so hopefully should be ok.

Beautiful post, a pleasure to read. Gentlemen should never underestimate simplicity. Look forward to reading more. C

Andreas Nestor

Wonderful post Simon!

I took your advice and visited the Haberdashery back in December, I walked out of there with the shawl-collar cardigan and it’s terrific. I absolutely adored their shop and the lovely service I received from Emily was one of a kind. Will definitely visit there everytime I go to London.

Thanks for an outstanding blog.
Best regards,
Andreas Nestor


This is excellent. Such a useful reference point and spells out the logical thought process one already has in the back of one’s mind.


Hi Simon,

Have you done a post on the G&G loafers? I searched but couldn’t see one. I see they are bespoke but are they based on a standard style? They seem an almost perfect bridge on level of formality (wholecut, but with lighter colour, hatchgrain etc).

Sorry if you have already answered this, I skimmed the comments and couldn’t see a response.


Peter B

Hi Simon, I know you rarely wear RTW trousers, but is there a manufacturer you would recommend buying RTW flannel trousers from? Thank you.

Jose Torres

I just bought shoes similar to the G&G ones here but instead from Ralph Lauren by Edward Green. Though they have no strap and may be a tad lighter. I believe they may basically be the Bamford model by EG. Would you say they could be worn similarly or would they not be formal enough?
Thank you!


Hello Simon,

Was wondering what size are you wearing for the A&S cardigan?
I am around 1.83 cm and 70 kg. Please recommend a size. Thank you.



If You should change the loafer for a “winter” version which type of shoe would You go for? I am thinking of a chukka in brown suede – could it work? Or?

Frank Jensen

Thanks for the advice.

Dan G

Hi Simon,

Are you wearing two different button down shirts here? A chambray made by Luca and another one? Or is there only one? I think only one but not 100% sure.




Yankee workaholic here from New York. I’m a former junior fashion designer turned corporate lawyer. I keep up with my love of classic clothing, always looking to acquire quality investment pieces that last. I don’t need much variety – I like the idea of a uniform. The advice you provide (in all media) is very helpful to me.

Though I work in “big league” corporate law, my particular firm is most likely the worst dressed firm in New York. Lots of suits sans tie, for example. My Monday – Thursday uniform is a navy blazer or sport coat, classic shirt with some pattern, and grey trousers.

I realize your advice of the usefulness of flannel trousers. My question is this: the flannels I have (all RL) are quite heavy — I imagine they are weightier than those you refer to in your writing. In New York, they work for October – March. I were to have pants made for me, can you suggest a weight (and perhaps a particular cloth) that would take more for a few months?

Thanks much.


Hi Simon, what’s the flannel pants’ fabric?


very interesting, good post


Would You ever consider wearing a tie in picture 4? If so would it still be the same brown Silk knit tie?


Simon, can I ask which make of socks you were wearing in post 3 ?


Hello Simon,

as of late, I have been thinkg about trouser hems a lot and would like to ask your point of view regarding hems for (pale) grey flannel trousers (wintery cloth). Would it be something you would recommend? What would be the thinks i should definitely pay attention to before making the final decision whether or not to have hems on flannel trousers ? Thanks!


Sorry, yes – tur-ups. Would that mean that flannels with turn-ups would be more a casual friday wear in an office, where most of the men wear suits or orther kind of business formal wear, rather than everyday wear?


Thank you, Simon, for the very fast response and all the info! Have a great day!


Hello Simon, sorry to bother you again, but i would like to ask, if you have any advice for cleaning light-grey flannel trousers? I have bought a pair and like them so much, that I have worn the for the last few days, just to better understand how they feel. The only downside is, that they have gotten dirty where the inner ankle bones are (i don’t know, if its from one leg rubbing against the other or the boot of the other leg). The label says dry-clean only. So should I just do that, and how often would be often enough? Or is there first aid solution after coming home from a walk? Any advice would be appreciated. thanks!


Your shirt is great, where is the cloth from?

Dan G

Hi Simon,

Do you know when the cloth will be shipped? Luca is here in NYC at the back end of next week so I was hoping it would arrive before then and I could hand it to him. If not, perhaps I could adjust my shipping address to have it sent direct to him?

Many thanks


A question about the tie! I’ ve got a dark brown knit tie for my birthday (chocolate). In what other combinations than the one you use it in (Blue jacket, Grey trousers) will a brown tie be udeful? I am thinking at light trousers (khaki) and ?




Simon, this is a brilliant post. I am looking to commission two blue jackets, to wear as separates in an office environment – one two button and one DB if i am brave enough. I like the elongated soft Napolitan shoulder (slightly elongated if possible as i am quite thin). I like what Solito and Caliendo did for you. Do you jnow when they are next in London and can you share contact details?


Thanks for the interesting article.

Is that a Cartier watch? Could you please let me know which model is it?….. I love the shape and the strap.


I just did, but I still couldn’t find the watch you are wearing here in the picture under section (4) of the article.

Drew Watson

Simon, I’ve asked several alterations tailors in my area this question, but I’m not sure they understood what I really want. So here goes: in traditional country tweeds, there is often a stitch, much like a quilt stitch, running along all the edges of the jacket — notably the lapels — and is not dissimilar from pick stitching. But I’ve read that this stitch runs all the way through the canvas layers and serves the purpose of supporting the floating layers when the garment (inevitably) gets wet. Some call it a ‘swelled edge.’ (https://www.google.com/search?q=swelled+edge+suit&rlz=1C1NHXL_enCA730US731&source=lnms&tbm=isch&sa=X&ved=0ahUKEwjo4belmv_fAhWLTN8KHUT3DYgQ_AUIDigB&biw=1707&bih=817&dpr=1.13#imgrc=ipfGkzM9ztCw6M🙂

So my questions are these: 1) what is that stitch properly called? 2) is it just a running stitch? 3) can it be added to a finished garment for look?

Thanks in advance.

Michael S.

Simon, I would like to ask a question relating to the first outfit: Do you usually wear your t-shirts tucked into the pants or do you leave them untucked?

Best regards,

Michael S.

Thank you, Simon. That sounds perfectly reasonable.

By the way: I really appreciate your highly sophisticated approach to describe and interpret the stylish properties of menswear clothing. Please do not change this attitude and your style in writing articles!

Best regards,

Shawn Ailawadhi

I am always in a suit even though my office environment is ultra casual. I just like dressing up.

Jeffrey S

Great article! In my workplace, a shirt and tie is compulsory but a jacket/blazer would be seen as overdressed. Do you think a shirt and tie without a jacket is still a good luck or would you opt for a more casual alternative to a jacket to put over the shirt? What alternatives would work? Thanks!


I’ve been taking a look at older posts (amazing how well your older posts hold up – guess that site title is more than just for shoe).

In any case curious how you’d feel about these hatch grain loafers with denim now. I know I asked another post about the G&G Chadwick and you thought those might not work as well with jeans, and I truly ask out of curiosity in terms of the difference. Is it the color and texture that make the difference here, or how the jean tapers?

I am considering a pair of G&G loafers for myself in the middle of next year and trying to decide between Corniche and Chadwick in terms of versatility, I do tend more towards tassels than penny.

As a side note, you convinced me to try G&G earlier this year – black oxfords (and you were right, I see why they are worth it now), and since they are ending the 20% of sale and I recently got a promotion I decided to buy the Hayes (I know I should have gone brown, but I couldn’t help it I think their Rioja will go well with grey and navy) as an X-Mas gift to myself.

In any case, I think I can comfortably do 2-3 G&G/Edward Green level shoes a year. I am trying to heed some of the advice you’ve given and using the “if you only had 5 shoes” as a template (already mucked that up with the Rioja). So any advice you can give on Corniche vs Chadwick would be helpful.

Shoes 4 & 5 are pretty set, a brown Oxford (Chelsea from Edward Green) and either a Dover or suede Banbury.

Thanks for the timeless content.


I need to ask, what you’re saying about G&G notwithstanding – would the Crompton work about the same as your bespoke model (for far future reference).

Would the Piccadilly in brown suede work just as well? It may be one of the few penny loafers that I like. Seems to me like suede Piccadilly and Begravia work with separates, flannels, and denim.

I am definitely using the capsule as a good base for buying higher end shoes, want to maximize usage. So, in my mind I have something of 6 shoe collection in mind –

1. Black Captoe Oxford (G&G)
2. Rioja Oxford – Hayes model (G&G)
3. Was considering the Corniche (G&G)
4. Antique Brown Chelsea (Edward Green)
5. Banbury in suede (Edward Green) or Dover in brown or burgundy Utah (Edward Green
6. Piccadilly in brown calf skin or suede (Edward Green)

For some reason my brain wants to get the G&G part out of the way first. If you are willing to take the time to offer thoughts (or any commenter) they’d be welcome. As I look at the list, the Monaco (G&G) in black calf might make more sense than #3.


Thank you. And yes, slow is the goal 2 (maybe 3) a year….only reason I got the first two so close together was that Covid left me some unspent money and the raise+promotion situation recently.

I think 3 (new 6) is being moved to the very bottom of the list.

On 5 – I lean towards the dover in burgundy Utah (I get the sense it would work with denim and flannel trousers, most non-suit/non jacket outfits) – but any concern about it being burgundy? Suede Banbury after that and brown Dover in smooth calf would be my least favorite option – any thoughts (obviously I’m only picking one)?

On the Piccadilly – I take their mink (dark brown) suede will work with everything from denim to informal suits? While the calfskin might be too formal for denim? Would the Belgravia be interchangeable with the Piccadilly (assuming the same material is chosen)?

You’re really helping my 2-3 year buying plans btw – you’re articles make me slow down considerably and be judicious in my choices – so thanks for that.


Thank you. I guess I just need to do some soul searching on Piccadilly vs Belgravia (my consultant – aka fiancee, is suggesting Piccadilly, but I need to sit on it some more).

I suppose I already made the mistake of buying Burgundy early (though I’d argue the Hayes takes the place of a black loafer, minus the ability to wear with some more casual pieces – and in a non-Covid world I will still be in a smart suit most of the time).

Point taken, I suppose if I do a suede Edward Green loafer 3rd, the derby is less of a priority, so a suede Banbury it is as shoe #4…and Brown Oxford from Edward Green 5th.

From there I can circle back about #6: Contenders being Corniche vs Dover in burgundy vs G&G Stamford vs EG Clapham in Brown Suede (G&G Stamford in the lead right now).

In any case, thank you very much for all your time, I really owe a consultant’s fee…guess I really should buy something from the shop.


Also to clarify things the G&G Corniche I’m considering as #6 is the brown suede one, though I can be convinced about the Black calf version.


I lied, one last question (if you’re willing to answer) because I’m a relatively strict planner when it comes to these things and like to sort of set things in stone (at least within 1 year timelines). Understanding that I’ve settled on an outline for shoes 3-5 (to buy over the next year – two years) I realized something that might help set my choice in stone.

If I am considering the G&G Corniche in mink suede as somewhere around shoe 7-10 (granted that’s a long time from now)….should it be Piccadilly over Belgravia? I figure:

1) the Belgravia in suede will work with jeans while the Corniche will not; AND
2) the Corniche in mink suede will work with more structured and formal tailoring where the Belgravia will not; AND
3) Outside of 1 and 2 there will be a great deal of overlap between these two brown suede tassel loafers

Thus, it would make more sense to choose the Piccadilly since it is an altogether different style for the first suede loafer given the consideration of a second suede loafer later? Or is this a non-issue that I should not concern myself with? If it’s a non-issue then I probably settle on Belgravia in suede, if it is an issue then the Piccadilly.

Charlie P

Hey Simon – could I make a request for an article suggesting ways to make the navy blazer/grey trousers outfit subtly distinctive? I feel like it’s such a foundational look, but can be a little boring. Things like swapping the plain button-down for a polo or piece of knitwear occur, equally adding pattern through a scarf or handkerchief, but I’d love your sharp take on it!


I love these type of articles as I think one of the biggest struggles for the average man is business casual! Is there a middle ground between 3 and 4? So not jeans but perhaps something less formal than the flannels? Would chinos work (and what colour)?

Ankur Garg

My favourite kind of posts.

Clifford P Hall

Simon, hi could you say more please about the blazer material and the source of the material.



Clifford P Hall

Perfect thank you.


Joshua George

How to differentiate stylish from dandy?
Would socks with loafers in a casual outfit like t shirt and jeans look affected or stylish?


This article is so helpful for showing how to elevate or lower an outfit for any occasion. I will add it to my favourites. With a few changes you could go from the pub to the CEOs office! Thank you Simon.


In addition – With outfits 5 and 6, do you think a pair of suede chukka boots would look acceptable as an alternative to slip on shoes?


Dear Simon,

Further to our speaking on the “Five paradigms” and having looked at this page as per your suggestion, I write as follows:

I think I would fall into the most formal category, i.e. six, however the article doesn’t quite answer my initial question (which is probably because I did not have enough time to write it more succinctly!).

Essentially I like tweed (a lot) and want to wear it at work but what should I wear to keep myself as cool as possible? For some reason I have the phrase “buggy lined” in my head; is that relevant? And presumably I am better off favouring a more informal style, such as Neapolitan? If so, what? Please advise.




I live in a tropical country and therefore one of the main problems being that more than half of the year it is seldom a good idea to wear layers and also an Oxford shirt could feel heavy. Also my office doesn’t require a jacket and therefore any mtm or bespoke shirt just looks too smart without a jacket.
What should be the go to shirt in these situations?


Sorry if my point did not come across clearly.
People do wear shirts and honestly some do it quite well. Most of the time what i have noticed is that i when i get off the rack shirts it is generally less of a problem because i can see the actual shirt and the lived in characterstics offered by some of the brands be it for linen or cotton tend to make it easier to wear without a jacket, but when commisioning made to measure i would often have to resort to a check shirt or a bolder stripe instead of a solid or subtle stripes to make it work with chinos or cotton trousers.
One of the problems which i have realised could be that the salesperson itself has not been trained properly to understand fabrics and weave and therefore it becomes difficult for them to give a proper suggestion with regards to my needs.
Maybe i am trying too hard to try and find an alternative to oxford shirts which i think may not be possible. Also i would keep these suggestion of yours in mind the next time i go out shopping.

Lindsay McKee

In the first photo, are the light Grey flannels a fox cloth?
what is the cloth for the blue sports jacket?

Scott Magoon

I just discovered this article, seven years after publishing, and I love it. The concept of showing the subtle changes to fit a range of situations makes this so much better than just a set of examples.


Yes please! That would be great.


I second that. I too came across it seven years after you wrote it, and was blown away by the simplicity and hence the usefulness of the article’s framework. I found the notion of moving up along the formality ladder by switching one item at a time to be very powerful conceptually and practically. Perhaps an updated article where you can propose more than one alternative to each item being switched can help (e.g., switch trainers for either suede loafers or chukka boots; switch denim for flannel, or chinos, or moleskin, etc.)


Wish I was at #5 but actually my office is closer to 2/3. And that’s at a financial services company in NYC!


Understand your pain. Same here in Chicago, most I can do is 4; I usually do 3/4. Too junior to go to 5.

Jack Linney

In my work, I typically bobble back and forth between (4) and (6), though I can wear (1) if I want to. I wear a suit to court and when meeting clients that expect me to wear one, but I don’t often otherwise. When I am out, I’d say (3) to (5). At home, it’s usually (1) to (0.5)—jeans and a sweater or sweatshirt in the winter.


Hi Simon,
I wonder if I might pick your brain on this subject. My office is totally casual at this point (sneakers, jeans, polos). I want to buck this trend entirely, but the challenge I’m facing is that I live in Florida, a tropical climate. It’s always hot.

A suit is too over-the-top, as is anything with a tie, probably. So I’m thinking of how to combine trousers/shirt/some layer over the shirt.

So for trousers, OK go with a high-twist. Easy enough.
Shoes can be loafers. Also easy enough.

The shirt, though. I guess an oxford? A little warm outside, but we’re climate controlled inside. Is a poplin shirt too formal if pairing with knitwear crewneck or a sport coat?
Maybe a cotton/linen shirt instead?

Do you find knitwear works here? Maybe if it’s cotton and not too warm? It would be too warm to go with an oxford cloth shirt and knitwear. Maybe a cotton/linen shirt and cotton crewneck knit?

For a jacket, I am guessing popular summer wool/silk/linen is too casual for an office. Maybe go for open-weave wool options instead?

Thank you in advance for your input.


Thanks, Simon. I appreciate the guidance.

I wanted to find a way to wear a collar (either via knit polo or collared shirt) and jacket.

I suppose you may be right about avoiding a sport jacket. Maybe I was over thinking it, wanting to stand out, professionally.

Looking forward to possible article.

Markus S

Just to add to Simon’s comment.

I have the PS polos. They are great, but since they are merino wool, they might be a little warm in Florida.

I also have the Colhay knitted t-shirts (also merino). Great, especially the ecru and navy ones, but same problem.

The Anthology knit t-shirts (cotton) could be better. They are not thin, but cotton feels more comfortable to me in the heat. The white is great, the cream-beige not so much (too beige/khaki for my liking).