Last week I explained why I find the knit polo shirt to be such a fundamental part of my summer wardrobe. 

This week, I’m using that polo and a pair of cream linen trousers as the basis for three different looks – three different ways of doing ‘smart casual’ in the summer. 

There’s no suit and tie here, but no T-shirt or shorts either. All three sit somewhere in between. 



As with the ‘which office’ article, I’ve kept the same colour scheme throughout, allowing us to focus on the materials and proportions. 

Those colours can be easily changed, and using warmer, less high-contrast ones would make each outfit more casual. As it is, the stark navy-and-white means this is probably the smartest colour option for each.  

With each look I keep the polo and linen trousers the same, but swap the outerwear and the shoes. 

The shoes and outerwear are broadly similar each time in terms of formality. But that doesn’t mean you can’t swap them around if you feel it works: I’d happily wear the espadrilles with the blazer, for example, though perhaps not the tennis shoes. 



1: Blazer and loafers

Outfit 1, the smartest of the three, combines the polo and trousers with a hopsack blazer and lightweight loafers. 

The blazer is my double-breasted from Elia Caliendo, in Naples, and the loafers are the Classic Sagan from Baudoin & Lange

A normal, Goodyear-welted loafer would also work, but the Sagan is particularly nice in the summer, with its softness and lightness. It’s also a little more casual. 

The blazer only works because it has a Neapolitan structure and cut – anything heavier would be too smart, and crush the polo collar. Even here, it has a tendency to move around and flip outside of the jacket. 

Grey or brown trousers, in linen or in a high-twist wool, would make the outfit less striking, and perhaps more office appropriate.



2: Overshirt and espadrilles

In outfit 2, the blazer is replaced with a linen overshirt, which immediately makes things more casual. There’s nothing like removing the line of a tailored shoulder to make everyone relax. 

The overshirt is an old one from Drake’s, with just two breast pockets and nothing on the hips. Personally it’s the style I prefer, but the current-season ones with two hip pockets are made just as well. 

The espadrilles are also from Drake’s, and are something I’ve been wearing regularly when the weather’s warm. It’s not an office shoe, of course, and not great for a long walk. But otherwise, in a dark colour like this, espadrilles are rather versatile.

They can be worn around the house, to the shops, and for work if everyone else is in trainers. They could also happily be worn with either of the other two outfits. 

I’ll do a separate piece on them, and the models I prefer, at a late date I think. The different brands and models vary a lot in make and last.



3: Bomber and tennis shoes

The last outfit, number 3, is the most casual. 

The outerwear is a suede bomber from Anderson & Sheppard, which is rather warmer than the other two jackets, even though it’s unlined. If you’re this casual, you might also feel you don’t need anything on top. 

But a lightweight suede is useful as a place to keep keys and wallet, and nice when the temperature drops in the evening. Plus it’s lovely against the skin. 

The shoes are plain-white Converse All Stars. 

The process that led to buying these shoes also deserves its own piece at some point. I spent so long trying to find a white tennis shoe in a slim last, made well. I tried over a dozen brands, from Spring Court to PRAS, Doek to Margaret Howell. 

But only Converse worked. The others were all off-white or too chunky. And these do achieve the Slim-Aarons-chic-poolside-waiter concept I had in my head. 

If anyone knows an alternative, made to a higher standard than Converse, please let me know. 



There are many variations on these three looks, and other variables we could have chosen. 

A nice pair of white jeans could make everything more casual, and would certainly work with outfits 2 and 3. Chic shorts would also be good. 

The polo could be swapped for a light-blue linen or cotton/linen shirt, if you wanted something smarter. And a grey T-shirt would make outfits 2 and 3 more casual, plus make the look less showy. 

Perhaps we’ll do another set later in the summer, keeping one outfit but just varying the material. That would be similar to the way ‘Which sports jacket’ played with materials as an alternative to ‘Which office’.

Hopefully each exercise makes you think, along a different line, in a different season. That’s the certainly the aim. 



Knit polo is the ‘Adrian’ from John Smedley.

Cream linen trousers are made-to-measure from Jean-Manuel Moreau.

Photography: Alex Natt @adnatt. Thank you to the wonderful Petitou cafe for the background.

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David G

I like the look overall, but cannot get how the espie has become a fashion item, let alone something people would contemplate wearing in an urban setting. Better to think of it as an outdoor slipper really.

As an aside, I don’t recall you looking at bamboo as a suitable fabric for a summer jacket or suit. I consider it to be ideal in many ways; light, soft, crease resistant and very hard wearing. And many of the wide range of patterns available would lend themselves very well to your preferred Italian style for a jacket.

David G

It may have been the case in the past, but I have a couple of jackets made in HFW bamboo (320666 and 320691), and they are very dry.

David G



I’m sure there are higher end brands that make Bamboo clothing but I live in Tulsa, Oklahoma. A normal summer day is between 92-105 Celsius with 60+ humidity! There’s only so much linen you can wear. Articles of Style made me a few suits and sport coats out of Bamboo. Soft, beautiful, do not wrinkle like linen and very breathable. Anyone in a hot humid climate owes it to themselves to at least try one!

Sebastian Flynn

Bamboo is just viscous, a semi synthetic fibre doesn’t really fit with the websites theme.


I have a blue checked Sportcoat in Bamboo from Sartoria Corcos, which is absolutely great. I don‘t find it shining either. The only flipside is that its a bit delicate.


Interesting Post! I think that Superga sneakers are more elegant and even comfortable than Converse. In addition they age better.


Hi Simon,
Not sure if you’d find them too similar and therefore no good, but check out the 2750-Cotu Classic Total White. Don’t really know the difference between 2390 and 2750, but the latter are super comfy and clean. I’ve had the all stars you have here too and I much prefer the supergas.


Hi Simon. A fan of all the looks but the sneakers on the last one looks off. I think a very casual loafer (e.g. paraboot or boat shoe) or a slip on sneaker like those carried by CQP ( may be better.

Ben R

Would you consider a boat shoe (mid brown leather style, as opposed to the sneaker-style deck shoes) as a substitute for the sneaker or the espadrille? I’m sure it doesn’t matter much. I was just curious where a boat shoe like this would fall on the formality scale.

Similarly, would a weejun style loafer be too formal/heavy for the first look?


Hi Simon, great to see a new version of your “different looks, different levels of formality” articles, here with a focus on summer attire.

Strange how I always felt espadrilles were only to be worn on the beach or by the pool when preparing a BBQ. All these (half-)sartorial looks with espadrilles I’ve been seeing lately make me reconsider this.

As for white shoes, may I suggest Asahi :
However, they look a lot like Doek models, so if Doek didn’t work, Asahi may not work either.



Hi Simon, ok I didn’t understand they had to be derbies. ^^

Here are other suggestions. I guess none of them fit your requirements completely, but I’d suggest you keep an eye on them during next seasons.

Shoes Like Pottery, made in Japan by the same factory as Doek or Asahi. You may not like the blue brand stamp though :

Naked & Famous, known for their jeans, makes some nice sneakers too. No white canvas ones at the moment, but hopefully one day :

CQP also makes some white canvas sneakers, but the Margom sole may not be thin enough for you :

Matt H

Personally I think the bomber looks smarter than the overshirt, the latter having a more relaxed fit and workwear vibe. I find bombers (at least ones like yours here – not vintage-style flight jackets) easy to dress up, being fairly interchangeable with a tailored jacket.

Regardless of that, I like all three outfits featured here.


Hi Simon

Great article as always, thanks. I am thinking of ordering the Drakes overshirt for summer (I’ve been looking for a while!), but I see they only have the khaki and brown this year. I generally lack colour elsewhere in the wardrobe – am I right in thinking the khaki is likely to be most versatile? For jeans, navy or taupe chinos, the polo in this piece, a grey t shirt etc. I see it as something to throw over everything and forget about.



Nice pictures. But shouldnt it be better with a little more contrast in color between the polo and the jacket?

I really like this kind of articles. I just think that it would be better if the polo was a shade lighter.

Jochen Schollaert

Is only navy under navy ‘pretty standard’? How do you consider other tone under tone combinations? Do they all work regardless?


Hi Simon, some nice outfits here. However, I have to say that I agree with MATT H. The structure of the bomber jacket vs the untucked (and loose) nature of the overshirt and possibly the brightness of your white sneakers vs the ‘beachiness’ of the espadrilles lead me think that 2 and 3 could be reversed. I am aware that you always say that the photos often don’t tell the whole story and I may have been influenced by your ‘power stance’ for outfit 3 and your ‘man about town’ slouch for outfit 2!


Did your search for trainers include Grenson Simon? They have a nice selection.


On the sneaker front. Have you had a look at Shoes like Pottery.


I don’t know if they are better made than Converse but I do love Shoes like pottery – my white canvas ones have aged wonderfully. And the blob is rather nice visually.


Hi Simon – shoes like pottery in pure white and just remove the blob. Easy to do and it will not leave a mark.


I know because mine is starting to de-attach in one of the shoes (in a similar way that the patch at the back of converse’s sole de-attach with time). Out of curiosity I pulled it a bit and noticed that there is no obvious mark. I just checked the other shoe and it is better attached (heat and glue?) but it is obvious that it is an independent piece of rubber. I am sure that with patient and a sharp blade it can be removed.

Niels Jensen

I am a great fan of espadrilles, when the temperature is above 25 C and I am not at work. I would love to read an article on espadrilles as I have also experienced quite substantial differences in sizing and lasting – as with no other shoe



Did you have opportunity to see/try the new private white brushed cotton Mayfair Shacket? If so do you think it would be a versatile piece to have (at the same level of your linen drake over shirt?)

Thanks and I wish you a great weekend


And how about the Crown Northampton-made sneakers? They’re leather, so maybe not for these outfits, but for the future?


Great article and photos. Thank you.


Hi, I think these images are super helpful, thanks! I was surprised to nice that somehow, for my taste, the trousers with the converse looks too short, whereas with the BL loafers they look quite nice. It may be just the photos though


Shoes like pottery have a nice white shoe

Richard Jones

Hi Simon, Shoes Like Pottery definitely. The blue blob is more subtle than you’d think. But the shape through the waist is perfect. Couldn’t recommend more.


This is where it’s purely about personal taste and preference. That blue blob is not subtle at all and just doesn’t look good. In my personal opinion that is. Clearly the people designing, making, buying and recommending these shoes disagree. Doesn’t really make sense to try and convince others of your personal taste / preference


For my semi-formal work environment I would probably wear outfit 3, but probably not outfit 2. I think the espradilles plus the looseness of the overshirt make it to informal – though I really like the look. Anyway, great post as always.


Hi Simon, another nice article.

I’m going slightly off topic here, but it seems to me that on the occasions Thatyou wear an open collared shirt, they often seem to gape more than they should. I’m not sure why – I generally undo two buttons myself, and see other guys who’s shirts don’t do this, but it always catches my eye.

I wonder if Luca faloni’s paramontura collars cure this?

However, far better a bit of gape than my pet hate, the tieless shirt or polo shirt fastened up to the neck.



Given corona I am planning to start walking into the office whenever it reopens (about an hour/ hour and a half) each day. What shoes would you wear? I don’t have many pairs that seem suitable. My BSLs wouldn’t be comfortable enough and my doeks might give way over time.

For reference I am in tech so can be as casual or dressed up as I please!


Hello Simon, Have a loof to for sneakers.

Ian A

Simon since the Crown Northampton sneakers have been mentioned twice now are they as well made as the Common Projects Achilles?


Hi Simon,

Very nice article. Do you wear you Sagan with no show socks?

I’m very curious about your future article about espadrilles. I always buy them in France (and made in France) for about 8-12 euros a pair. They last one or two seasons with fairly intensive use. I’ve seen much more expensive models (I guess the Drake’s ones belong in this category), and I find it hard to justify the price given that they are not repairable in any way and fairly short lived.

For white canvas sneakers:

Some are more natural cotton color than bright white.

And a truly fantastic model of “sneakers” (resolable) by clinch boots which are probably quite far away from what you are looking for but worth a look anyway:



Hi Simon, I assume the Drakes espadrilles soles are stiched? Haven’t been an espadrilles fan for a while but bought a pair of H&M to see if the style works for me – it does, but the cheaply glued sole is falling apart after a few wears. Though, I do love the blue-white stripes design of them as this colour combination reflects summer for me – if anyone has a recommendation for a similar design with better quality it’d be much appriciated.


Hi Simon,
Really nice article showing causal summer style and how changing one or two things can change the overall look. My 2 cents, I think #3 is slightly less casual than #2.
I have a pair of tobacco brown and absolutely love them , on the other hand, I’ve basically always found cream (and adjacent colors), in linen, to be too see-through to be a viable option. Can you comment on the material for the cream trousers in this piece.


Hi Simon re gape ( I don’t seem to be able to add the comment to that thread). I think it’s combination of a bit more chest than I would like personally, but also that in the open bit of shirt one side folds over a bit and kind of collapses, rather than holds a clean line You can see it on the polo shirt in this article.

My Faloni linen shirts have a a bit behind the placket and buttons which flares out towards the top, and it seems to hold its line better when you are unbuttoned (!).


Really enjoyed this post and these looks. I always find Vans Authentics are a good simple summer shoe. I find they wear almost like a deck shoe. The all-white and the cream (with blue stripe on the midsole) would work well here. The only downside is that they have a small Vans label on the side which some people may not like, but has never bothered me.


Espadrilles are great for warm weather or on holidays. Try Castaner, the Pablo model in suede is my preference


Love that bomber! Does it come in other colors?


Hi Simon,

This is in reference to your comment regarding wearing a Neapolitan-cut jacket. Would you ever wear a cut with a stereotypically English cut, like Whitcomb or Steven Hitchcock, with a Friday Polo or even a sweater polo, but in an appropriate fabric/style (for example, a Donegal tweed)? if the issue is the collar alone, as opposed to the more structured look of an English cut, I think a Friday Polo would be fine (and frankly, although you might disagree, I think would be fine with a Smedley merino polo, as well).

Leendert van Nieuwenhuijzen

Hi Simon,

I really like the Onitsuka Tiger Mexico 66 sneakers like the white ones mentioned below.

Christopher Lee

I just started getting into espadrilles this year, in anticipation of summers walking around National Trust country houses (which may or may not come to fruition). I find the suede ones, such as sold by Morjas, are slightly smarter than canvas, and if you can find a version where the rope portion of the sole is dyed to match the upper (Suitsupply actually has one), that adds to the smartness.


Dear Simon,

nice combination, as always! Camino71 (small German brand, model 71 low white) or Tennis from Ludwig Reiter may an alternative to your converse.


You are right, there is no canvas option…. but for canvas I guess the only option with slim last is Converse :—))


tried the Muji Water Repellent sneakers??


On the topic of espadrilles, Ludwig Reiter also has a nice variation (though in fact suede and with a crepe sole) that is a little less beach-like but still has the vibe. I wear them as slippers at home:


If I’m looking for a slim simple sneaker for wearing under jeans or a chino I like to wear a German army sneaker. They are i think from the 70’s. They can be found for 125 euro but a lot cheaper too if you’re not looking into these hip vintage places.. I bought them for 25. It’s a good shoe if you ask me. I like the combinations but I think the upper two make you look a bit older than you actually are. The blue bomber looks great. Thanks for the post. Cheers.


I am going to commission a bespoke smart casual cream trousers and currently I am thinking either using the Quest Cotton from Huddersfield New Fine Worsted / a Japanese cream denim. I rarely see people using denim for making smart casual trousers but to me it’s more robust and will more likely to hold its shape and pleat. What are you thoughts on this Simon? Thanks


Just would like to follow up on the subject. I was thinking of using cream denim for chinos as I noticed denim in “trouser cutting” is getting more common. Would the Quest holds pleat significantly better than denims? I am afraid the Quest would be too smart to pair with t-shirt / casual linen shirt. Cheers


Quintessential ‘Permanent Style’ – some great looks.
I have a capsule wardrobe that I use for extended summer city breaks.
It is essentially the same as illustrated excepting I don’t bother with the bomber jacket but also take a pair of light grey linen trousers and only one pair of shoes – a pair of chocolate brown, tasseled loafers – that I think are much more appropriate and practical for the city than those illustrated.
I’ve spent three days in Venice, Paris and NYC and have been flaneur ready for all occasions!

rakan william

Unrelated to the topic above, however, I’ve seen that you have studied philosophy, now, I acknowledge that I’m no expert on the matter but I’ve found a very hard time justifying everything I want not because of cost but because of the belief that I don’t need any of these things and even more terrifying is the thought that I only want these things because I am missing something else in life something I have not yet identified and having too much scares me because it never ends you always want more no matter what you have so my question is do you have a certain life philosophy regarding this subject and I apologize for the lengthy and personal comment

Jochen Schollaert

Sneakers: I know they’re leather, but these are well made; I have the high tops:


Shoes Like Pottery have an all-white model.

Erik Schedin also does canvas sneakers from time to time, though I think these are running low on sizes and colours.


Hoy does the Anderson & Sheppard Bomber compare to the Valstarino?


Hi, great casual outfit. If you had choice between chocolate brown or navy linen schaket bomber which colour you would choose? Which would be more versatile?Thx


Regarding the Sagans, which shade of brown suede do you think would be best for a first pair? Dark brown, bark grey, or brown oak?

Rupesh Bhindi

Hi Simon,

Please could you provide the fabric details of the cream linen trousers and advise if the made to measure by Jean-Manuel Moreau compares to your other bespoke trousers.




On Rakan William’s comment, and your reply on caring for clothes, my grandfather advised me to look after all my clothes as if I would never be able to afford a replacement. Great advice as I’ve still got, and wear, items I bought over thirty years ago!


Isn’t the Converse All Star a basketball shoe, and not a tennis shoe?


Hi Simon,
Strangely enough, I’ve never seen a post devoted to the Harrington Jacket on PS. Frankly, I don’t know why. Would it be a prejudice of yours?
I hope I would deserve an explanation.


Thanks for your reply, Simon. To be honest, I don’t see how your rationale does make sense.
Indeed it doesn’t and can’t annihilate the sheer fact that the Harrington jacket remains a great piece for Summer.
And I musst add that I really do not see – as to levels of formality – such a difference between a Harrington jacket and the kind of suede jacket you are wearing on the pic above. Beyond suede being more expansive than cotton, I can’t figure out how a jacket made of the former could be smarter in matter of style. For both could exactly be cut the same way.
I remember the first Harrington jacket I bought while in high school had pockets cut like yours on the same pic. For years, it had remained the most expensive piece of wardrobe I had ever bought. A huuuuge amount of money back then.
Of course this kind of jacket could be worn with the same pieces you would wear with a suede jacket: from trousers down to shoes (loafers not being the single ones you could chose from).
We are speaking of … Summer smart casual items. Aren’t we? How then could you even envision a suede jacket to even be considered. As no matter how this leaher has been tanned and proccessed, it will remain heavier than cotton. Unless you ditched the notion of praticality as being irrelevant to style.
On many occasions, you have professed your interest in Ivy style (see the recent post on Ralf Lauren). How could one show such an interest to this specific style while ditching the Harrington jacket as being “rather more casual” (than suede jacket, and even the shawl collar cardigan, I suspect) is totally a mystery to me.
Yet I must confess that I doen’t own a Harrington jacket anymore, even though I do have a very well French made suede jacket. Indeed, surprisingly enough I’ve realized that I can’t find one that really meets my expectations, and for sure not the level of craftsmanship of the one I bought … decades ago.
The only one I’ve seen so far about which I could be willing to compromise perhaps is the jacket sold by The Armoury.


Hi Simon, I was going to ask you the same question about you and Harrington jackets on the John Simmons article but its a good thing I found this comment thread through the search box.

Now to ask a more specific question, what are your thoughts on Baracuta’s Harrington jackets? Is the quality worth the money? Or is it more of a high-street brand milking its heritage for profits? (apologies for being blunt)

I know you’ve previously recommended PW’s Harrington’s but the copper snaps on the collar doesn’t really appeal to me. I much prefer the buttons on the Baracuta models.



Great thanks Simon!



Those JMM cream linen trousers look fantastic. I am assuming that you will cover them later in your review of your JMM suit?

Also, on the topic of cream linen trousers, you posted a picture to your IG stories recently with you in a looser fitting pair under the title of Chic Summer. May I ask who the maker of that pair is?

Given how hard both summer dressing and casual dressing are for me I really appreciated this article. Please keep helpful content like this coming.


Great article.

Regarding Converse, I believe they offer a heritage model which is slightly higher quality. I haven’t tried Novesta but these may be worth a look too.

You may like the YouTube channel (Rose Anvil) where the guy cuts shoes in half to see the quality.


I am sorry if it’s been talked before but I’m kinda new to all things sartorial. Are you saying that only unstructured jackets can be worn casually? Or is it a personal preference? What happens if someone prefers more structure because he thinks it flatters his body type more? I highly doubt the average person you meet notices the shoulders being soft for example or that the jacket is structured as long as it’s in a casual fabric that works with the rest of the ensemble. I had trouble deciding what I would be more comfortable with and because there are zero bespoke or good mtm options where I live I bought online 2 heavily discounted suits, one from Tom Ford and one from Attolini. They are both pretty comfortable but I prefer the how the more structured one looks on my body type and that’s the direction I see my wardrobe evolving. No one ever noticed big differences between them even when I asked, for most one is blue and one is grey.


Glad to see you finally endorse good old Chucks. I have been a fan for decades, while sceptically reading praise of much more expensive trainers such as Common Projects, on the basis of an elongated last. Chucks have it, look no farther.


Hi Simon,
Nice watch.Riviera cool.
On a different topic,do you prefer canvas sneakers to leather ones and if so why?


I have a pair of Sagan Classics in dark brown, which I’m enjoying very much. They’re comfortable and incredibly versatile – I’ve worn them with everything ranging from high twist trousers to shirts.

What’s your recommendation for a second or third pair? Would you recommend sticking to suede or trying one in deerskin? And if I go the deerskin route, do you think it would make sense to “step up” to a Grand or stick with the classic?


Hi Simon,

PWVC have a Harrington in Linen and a Zip through Linen overshirt (with just the two pockets). Would you consider either of these instead of the buttoned overshirt ?
Also, wouldn’t a Denim Jacket work as well instead of the Blouson ?


Nicolas Stromback

Ah yes, this is great. I have been wearing the exact same variations with one style of pant. Its interesting how certain things go so well together with the same canvas, so to speak. On another note, how have your Sagans worn? Have you “worn out” any of them yet? I have been contemplating buying these or a welted, unlined pair instead from say EG.

Shem Teo

Hi simon are there any brands that would recommend for t-shirts which are solid in value and lasting (but not too thick). Also have you tried any short sleeve shirts thst you would recommend?


good ideas. for some reason i find the utility jacket outfit more casual and laid back than the bomber one. also for some reason i cant get around wearing short sleeves tops with blazer jackets. the blazer against the skin on my arms and no cuff at the wrist feels really awkward for some reason.


Hi Simon. Enjoyable reading as usual. So would it be PS heresy to even think of canvas shoes from say adidas or sperry or seavees? They make pretty neat canvas sneakers


Thank you this article Simon.
I’m currently waiting for a pair of Drakes espadrilles to arrive!


A bit late on the uptake here, but A+ on your Slim Aaron’s reference in section 3. I’m definitely seeing outfit 1 at Hotel de Cap or the B&T in Palm Beach where he would have been sure to snap your photo. If you like the Aaron’s genre and have nothing else to do one Sunday afternoon, google “Ellen Ordway NY Social Diary” and you will see numerous listings of her hundreds of photos of a bygone East Coast American resort life primarily in the 1960s. With the accompanying text, you will find American social history at its finest via her amateur, home photography. All very starchy, but that was the era. More importantly, great navy and white post. Thx.


Correction to above comment: last line should have read “navy and cream”, not “navy and white”.


Hi Simon,

I like the cream linen pants do have the name of the manufacturer and the swatch number.




One thing that popped into my mind when reading this post and the previous one in the series, is that the polo doesn’t really work, even on its own, in my humble opinion. I think it fits we’ll in the sleeves and torso but pulls a bit in the placket and the collar just looks flimsy.
I think these looks are marvelous but I’d opt for one of the short sleeved knit polos Saman Amel and now berg&berg offers. I think that collar looks better especially when worn sans jacket.

I really appreciate these kinds of posts, by the way. Keep em coming.


Perhaps the drakes one you wrote about recently for their site? The sleeves and cut are perhaps a but less casual, but collar looks like it’d fit well under tailoring at least.
I have no personal experience, but I find in theory, there’s a range from Iolo Korea that would fit the bill quite well,


I’ve got a pair of tobacco Sagans which work great with jeans. I’ve also worn them with light khaki or cream colored trousers. Do you have any other suggestions?


Which of the Sagan designs do you prefer? Seems to me the plain apron one is sleek and minimalist but looks a little like a slipper; the one with a tassel avoids that association (looks more like a shoe) but runs the risk of looking effete.

Dan James

Love following your site from afar as I am based in Japan. Not sure whether you can get them in the UK but Converse have done a lightweight all-white Chuck Taylor here for a few seasons now and they are my go-to-shoe for weekends here when the real heat comes (35℃+). Here they are-I’m afraid the site is all in Japanese but assume Professor Google can find a way around that.


By the way, the Converse web site lets you put together your own custom Chuck Taylors, so it’s possible to design your own off-white version and have it shipped wherever (I have an all-off-white version that I wear constantly).


Trousers look fantastic! Were they made by a certain chainsmoking neapolitan?


Perfect looks 😉 I love cream linen trousers in summer. But I don’t like espadrilles. I can’t wear shoes without socks.


Hi Simon!

I’ve been meaning to ask this question and this article appears to be the most apt so here goes – as someone who works in the “tech industry” (think Silicon Valley and the classic jeans, t-shirts, hoodies, sneakers combo), thoughts on balancing the desire to wear classic menswear pieces such as those here on the PS site and described in this article versus fitting in the office culture?

I know it may be easy to say “You are who you are, wear what you want.” but would love your thoughts on this matter. I wonder if it’s more around “a jacket may be too much but an overshirt is more casual”

Thank you!


Ah. I have not seen this video. I will definitely have a watch right now while I have my morning coffee and breakfast, perfect for a Sunday morning here in the Bay.

Noted on the Casual Clothing category as well, will keep browsing through that.

Thank you again, love and appreciate the content – always looking forward to seeing the newsletter come through my inbox!


Hello Simon,
Great article as always.
Do you think that the following combination would work:

– keeping the rather “casual unlined blue blazer”
– replacing the blue polo by a white one
– linen/silk mix light “latte” trousers


Thank you for this great read, Simon. Would you believe swapping cream linen for cream wool gabardine would also work?



Do the suede sagan loafers pair well with chinos (not workwear, but not necessarily anything too formal, either)? They obviously work very nicely with linen tailoring, but I’m wondering just how casual they can get on the formality scale.

Dennis Bush

Hi Simon, nice post. Does anyone make a casual linen shoe for summer wear?


Hi Simon, maybe these
you like them, total simplicity.


Hi Simon,
In your opinion, if I could only choose one due to budget constraints – would you say cream trousers in cotton or linen were more versatile (for the purposes of mostly casual outfits and the rare sport coat)? Or would there be an even more versatile colour for casual trouser/chino (other than khaki/beige)? Appreciate your every post and engagement.


Hi Simon!
I just love reading your articles and so amazed to learn how easy it is to be well dressed. Thank you.
After reading your article i have also to decided to buy for myslef a good navy overshirt for summer months. I just had one doubt in mind and would love your advice.
1. Can i wear dark olive green chinos with navy cotton overshirt or do you advice that there should be a considerable amount of difference even when wearing an overshirt as you generally propose for sports coat?


Thank you so much for the reply Simon!
Certain times you have also suggested that a person can play around with fabrics to create much needed difference between trousers and jacket if i am correct.
What would be your opinion about ‘navy blue cotton twill overshirt combined with dark olive green linen trouser’? Would the fabric over here create the much needed difference according to you?
Do you believe that for such casual jackets the rules are not that strict? I can totally understand the rules for sports coat and blazers because there is a risk for it looking like a mismatched suit and therefore in your opinion can i try breaking up these rules for such casual jackets?
I am putting forward this question for the sole reason that sometimes during night out at a pub or certain similar places i find a light colur trouser to be a bit inappropriate for the occasion and therefore looking to find a solution to it.


So would you suggest going forward with this combination?


Hi Simon! Merry Christmas to you and your family.
Love reading your articles and so very kind of you to have solved so many doubts of mine.
I was going to order a ‘dark brown overshirt’ for the summer/spring months and therefore was going through your articles on safari and overshirt to get a brief idea and your piece advice on it and while reading your articles, certain doubts arose in my mind and therefore would your advice on it.
1) Most of the overshirts you have worn seemed to me to be a bit larger than what would be for a regular jacket. Can i make an overshirt for myself the same size as my jacket? If not then what should be the correct fit?
2) What cloth should i chose for my overshirt so that it could also be worn with denim? Can i go for cotton- linen mix for my summer and spring months and wear it casually with chinos and denim?


Loved the outfit in which you are wearing an overshirt. One advice needed if you could help.
Can i keep the whole look the same but just replace ‘espadrilles’ with dark brown penny leather loafers? Would leather penny loafers match the outfit?


Hi Simon!
Could this linen overshirt or perhaps a cotton overshirt for instance be worn with a dark indigo denim jeans?
Would love to hear your reply!


Hi Simon, consider perhaps Seavees Racquet Club or Monterey sneakers. Let me know what you think. All the best for the season, Zeke


Actually their website makes a great deal about them being vulcanized. The racquet club seems to be discontinued although available through third party vendors. I have 4 pairs, the only complaint being that the side strips can get grubby.


Very informative post Simon.
I really want to wear jackets but was not able to do so because nobody around me would wear one. After reading so many articles of your i am fully satisfied with the view that i can wear an overshirt without looking out of place.
I would be going to a tailor and would be asking him to make a cotton overshirt for me which i could wear even with jeans. My only consideration being that wouldn’t a material such as cotton look more like a shirt rather than a jacket or am i wrong in thinking that?
I have never ever made an overshirt for myself and so very naive in these things. Any advice from your side would be of great significance.


For summer and spring months what would be your preferred fabric for an overshirt?


Hi Simon!
I have a dark brown cotton overshirt from H&M. Can i wear a dark brown shoe with it or should i go for burgundy?
Would dark brown look too matchy because i don’t find the shade to be too different?


What size are you in the Drakes linen overshirt? I’ve always liked the piece and find that I’m fairly consistently one size below you. Thanks!


Hi Simon, great looks and article! I’m looking for a linen overshirt and I’ve come across this one from Flax London: Do you (or other readers) have any experience with their products? The style looks similar to yours by Drake’s, at least for the pockets. Thanks


Thanks, that’s very interesting news.

If it’s not too much to ask, could you tell the price range? I’m sure it will be an excellent piece, but it’d help to know if it would fall roughly in my budget. I totally understand if it’s not yet set, of course.


Thanks Simon!


In the second look how would a tshirt with sagans look.
Would swapping a shoe from espadrilles to sagans make much bigger difference in formality then shifting from polo to t shirt?


Simon I find navy knitted polo to be more formal than navy chambray or navy linen shirt. Do you also feel the same?


Do double pockets look good on chambray shirt? I want to wear it without a jacket


Hey Simon,

Maybe this could be a good alternative to Converse?

Wasn’t all that impressed by their leather sneaker, but this one seems to tick most boxes, save for the fact they’re off-white.


I always thought espadrilles to be a substitute to slippers, but your article has convinced me to think that it can also be a good alternative to sneakers if ‘long walks is not involved’.
Do you think on a casual Friday when everybody else in office is in trainers, then would espadrilles look good?


The reason I am asking you this question is because I want to know till what extent could espadrilles be used.
Would in an establishment or venue which requires closed toe shoes, would espadrilles fit the bill?


Hi Simon, could I ask what size you wear for the A&S suede bomber? Also, would the jacket only be wearable during the UK’s spring and summer?

Many thanks,

Joe Pickering

Hi Simon, with summer approaching, I was wondering if you ever found an alternative to all white All Stars that you were happy with?


Rui Lima

Hello Simon,

Please have a look at these:

John Lennon used to wear them…


Hi Simon,
May I ask what it was about the Doek’s that were problematic for you? I thought you liked them a lot. Were they just too cream/off-white as opposed to white, and you prefer the white for summer?


Oh did you go for the indigo AND white?

I checked out their website and only white is available (I think they have a store in NYC which I may visit).


Hi Simon,

I have been looking to pick up a piece of Navy Suede outerwear for a wild now. After heavy consideration I have narrowed it down to:

  1. Navy A&S Bomber (pictured in this article)
  2. Navy RLPL Harrington (pictured in your t-shirt article)

I wanted to ask your opinion on the usefulness of both garments and any differences you have found. Which one would you recommend for someone who will only add one piece to their collection?


Hi Simon,

It does indeed complicate things! Found the RLPL size for cheap here in Japan, so considering pouncing on it.

Regarding your A&S Bomber, I remember you said you took a Navy. The site says it fits slim and recommends sizing up. Do you feel that is the case for yours? Also, do you still wear the jacket regularly?


Hi Simon,

Decided to hold off and wait for your Navy Suede Jacket next year!


The sagans look rather pointy at the toes. Did your feet ever hurt after wearing them?

Also, do you recommend wearing socks with them, or barefoot?


Would outfit three look of sneakers with linen trousers look appropriate with a casual shirt instead of a polo?


I thought when you mentioned soft breathable shoes with casual shirt and trousers in the summer chic article then it also included canvas sneakers. If I may ask then could the look be not part of the summer chic wardrobe?


Simon, I realize that your stated the Drake’s overshirt is in linen, but I came across this on ebay ( looking very similar saying this is in wool-linen. Could you kindly confirm which is the case?



Hi on the subject of tennis shoes, have you tried Moonstar? I find their Gym Classic style perfect, looking sleek with a good fit through the waist. I think they are linked somehow to Shoes Like Pottery, but the bonus is they don’t have the “blue blob” – I don’t like that either!!


I have read in your post about tan shoes that with a darker shirt tan shoes doesn’t look good and I know with white there is more of a leeway but in the third look if I replace the cream linen trousers with dark olive linen trousers and then pair it with white canvas sneakers then would the outfit look good because now no piece of clothing is light in color?


how would a normal napoleon jacket compare against the double breasted jacket? I am thinking about buying my first summer jacket (the decision is between a hopsack linen or a linen db jacket (weave unknown)) both in navy. Also would you wear white leather sneakers (common project) with the double breasted jacket? Sure the trousers have to be darker in that case…