I just got back from our annual summer holiday: two weeks in Portugal, in a villa with my wife and children, miles away from anything. 

I normally write a post running through things worn on holiday, as I know readers find it interesting having different perspectives on style. 

But rather than just go through it all, this time I thought I’d highlight the reasons behind the choices, and the role I think propriety has. 



Men find it perfectly natural to consider what’s appropriate to wear into an office, or into a meeting. Shorts are unlikely to be appropriate for the former, and you’re likely to smarten up a little for the latter. 

But with casual wear, these considerations often go out of the window. Suddenly anything goes, and the results can be disastrous. 

On the flight on the way out, I saw one father wearing cargo shorts, a brightly striped polo shirt, a tailored jacket and tan brogues. Nothing went with anything.



Shorts are a good dividing line in terms of propriety. For men they are often the clearest indicator that this is time off. 

A friend told me years ago that they’d never wear shorts in the city, and over time I understood why. Being in a city, or a town, means going to restaurants, hotels, shops – interacting with other people in their environments. It’s natural to be a little smarter as a result.

Contrast that with where we were on holiday.

On our own in the countryside, in and out of the pool, occasionally driving to the beach. There’s no one there to be appropriate (or perhaps better, complimentary) towards. 



It is in that situation that I’m perfectly happy wearing a pair of shorts, a T-shirt and an old kendogi Japanese jacket (pictured above). 

They’re practical clothes, to run around the pool in, play in the garden, change out of into trunks at a moment’s notice. 

But they’re still all pieces I love for their quality, their cut and even their beauty. You can see close-ups of that jacket at the bottom of this post.

When we went to town for a coffee, or out for dinner in the evening, I’d likely change into trousers, a shirt and knitwear or some kind of overshirt. 

It was probably more appropriate, but it was also enjoyable to do so.

As long-term fans of menswear will tell you, half the pleasure of being well dressed is separating these kind of occasions deliberately, and creating a little structure. 



In the image above, I’m wearing something similar – though in this case, merely for dinner at home because it was chilly. 

The linen trousers and cotton sweater are enough in the south of Portugal, where it might be 35 degrees during the day, but 15 in the evening. 

I should mention that it’s possible to be overdressed in this way, too.

I know friends who’ve gone to the French Riviera intending to wear nothing but cream tailoring, espadrilles and a panama hat. Unfortunately no one dresses like that, and you’re just as likely to be inappropriate as you would be in a vest and flip-flops.



On the point about shorts, I think this extends to questions readers ask about weekend clothing at home. 

If you’re playing with your children in the park, shorts are great, in the city or not. I remember one tailoring enthusiast wearing a suit and DB waistcoat to take his daughter to the swings: it looked ridiculous, like costume. You might as well be wearing a lace collar and a powdered wig. 

There’s nothing wrong with wearing shorts when they’re clearly suitable. Just make them good ones: not bermudas below the knees, not tight little running shorts, not baggy ones with 17 pockets, nothing with a loud ‘fun’ pattern. And a good T-shirt or polo too. 

Caring about fit and quality in this way is the best way to avoid the biggest risk of middle-aged men in the summer: looking like a schoolboy. 



I can imagine a newcomer to menswear thinking this all sounds silly. That it’s overthinking essentially casual, relaxed clothing. 

Perhaps. But you have to wear something. And if you care even the slightest bit about looking good, this is the reasoning to consider. 

You don’t have to dress like that: you might have a particularly flamboyant character and want to be like no one else. But it’s still worth understanding the rationales, because they’ve driven clothing for a long time – just like ideas of complementary colours, complexion or cut.

I think it will mean you understand why someone just looks good in their clothes. And it will give you more confidence in what you wear, too. 

At the very least, nice to base decisions on something other than how many influencers wear a particular trainer. 



Right, enough preaching to the converted. The clothes pictured are listed below. Any questions about any of them, let me know. 

Enjoy your holiday, if you haven’t had one already. I already miss the feeling of sand between my toes.

First outfit:

  • Khaki shorts from Permanent Style
  • White t-shirt from The Armoury x The Real McCoy’s
  • Kendogi indigo jacket, vintage
  • Suede loafers, Alden (the ‘leisure handsewn’) via Trunk
  • Red cap, Holiday Boileau



Second outfit:

  • Navy cotton sweater from Private White VC x Inis Meain
  • Olive linen trousers from Paul Stuart
  • Brown-cotton Japanese traditional bandana, Anatomica 


  • Indigo canvas trainers, Doek via Trunk
  • ‘Cal’ Berkeley cap, gift
  • Yellow cotton beach towel, Trunk
  • Chambray camp-collar shirt, Gitman Bros via Trunk

You can read the three previous ‘Holiday snaps’ posts here.

Close-ups of that vintage Japanese jacket, a gift from a very kind friend, below. Read more on the appeal of vintage Japanese fabrics here.


Notify of

Inline Feedbacks
View all comments
Paul Boileau

I may have to get one of those boileau caps……..on second thought maybe not…..don’t want to end up looking like William Hague…..


Or even Trump – “Make Style Permanent Again” anyone?


Yes, unfortunately for a majority of us Americans, a red baseball cap with white lettering has been ruined for the next 10-20 years.


Sensible stuff! On a spontaneous beach outing last week I ended up improvising with swim shorts, an oxford shirt and an overshirt, and espadrilles. I thought it was a decent improvised look, but my family found it hilariously incongruous. A good reminder that our internal logic often doesn’t work for others, for good reason.

My favourite outfit this summer has been Uniqlo’s wide baggy t-shirts, tucked into high-waisted pleated chinos, with espadrilles. Really nice balance between simple, casual and elegant, in my view.

Shorts: most of mine are old chinos that I had shortened and cuffed. Cheap, and better than most shorts you’ll find. I only wear them in casual summer situations so I don’t mind that they already look worn.


Yes, espadrilles have an amazing range. They’re basically canvas loafers, minimalist and humble.


Dear Simon,
Being on a budget, each piece of tailoring is carefully thought through. My usual tailor is Whitcomb & Shaftesbury, as they are the only ones I know off offering such a high-quality level at their price point, which is the only price point so far that I can more or less afford.
However, since I do not live in the UK, I have to factor in my regular trips to London, which I mainly do in order to go see my tailor, either to pick the cloth for a new order, or for a fitting. I’d usually stay overnight and profit from this occasion to do a few other things in the city.
Out of curiosity for my next garment, I contacted some other houses on the row, such as Henry Poole or Anderson & Sheppard or Gieves & Hawkes, some of which are offering trunk shows in my home country.
This is when I noticed the price difference between W&S and G&H or Henry Poole is equivalent to the cost of about a tad more than 3 trips to London (in which I considered the flight, transport in the city, hotel and food).
Hence, is the make and quality “better enough” at some of those well known, old house to justify investing there rather than at W&S and “skipping” 3 trips to London?
Thank you

Sam Tucker

How do trunk shows work? Doesn’t bespoke require several fittings, so do they do the fittings super quick within a few days, or do you just have to wait for the trunk show to show up again next year for the next fitting or can they do bespoke with just one fitting?

Jan Willem

That’s exactly what I struggle with. I just received my first bespoke shoes ever from an Italian maker. Ordered in May 2018, tried fitting shoes in November 2018, received the final pair in August 2019. Lovely shoes but there are a couple of issues with the fit and I am hesitant to send them back because I don’t want to wait another 6 months or year for a revised pair! No doubt that some makers are more user-friendly but the whole trunk-show-visit-twice-a-year-or-whenever-I-feel-like-it formula sucks balls in my humble opinion

Ian A

You have to wait until they next visit your city from a Trunk show to have another fitting.


Great article!

I must say that I may disagree a little bit about cargo pants and cargo shorts. I think that they, in muted colors, are very practical on vacation. You have a place for sun glasses, a power bank and maybe something else. They are not as smart as regular pants/shorts but I think there is a trade off that could be made. The cargo pants and shorts that I own are from Incotex in a pale cotton-linen mix and I think they work with a tee or polo shirt on vacation. Am I totally wrong?

Peter K

Maybe a small backpack for the stuff you want to carry.


I desperately wanted that Gitman shirt but they ran out of my size! Simon I blame you!!


Hi Simon.

Is it not too strong of a statement to say that wearing a suit and DB waistcoat to take his daughter to the swing looks ridiculous. Not that I would dress myself like this to go to the park. But I refer to your previous article about Gauthier Borsarello, who says that there are no menswear rules (nice article by the way and thank you for having included the link of his radio interview). I know that you do not necessarily agree with this statement, but I would think that there are no established dress rules when playing with your child or children in the park.


I think it’s really a context issue. Look at this from those angles:
1. It’s a bank holiday, you’re off work, and you plan on going to the park with your kid. You especially dress in a 3 pieces suit for that => was it really necessary? Will you then be willing to go run after your kid in the bushes and clean the dirt out of him after falling in your 3 pieces suit?
2. It’s a working day, you’re at the office in your 3 pieces suit, and have the opportunity to see your kid that day over an extended lunch break and quickly pop-up to the park.
The context here is what makes the difference.


Thank you or your input Simon and Joel.

Yes, indeed context is important but, in my opinion, attitude is important as well.

If you wear a three piece suit in a park because you want to show off or, as Simon mentioned it, you think that this is how to dress properly when you go to the park, then indeed it is somehow inappropriate.

But if this person is genuinely feeling pleasure being dressed like this and if it is really “him”, then I would have a tendency to say “why not”. Even if it comes with a discomfort when he has to do activities with his kid(s).


I don’t know if it would be useful for you to do a quarterly post where you give a (v rough) outline of what we can look forward to. There is something annoying about commissioning something / diving into something when a post pops up a month later.

Even if you just say I will be focussing on expanding my suit style posts as well as looking at tailors from this region / design from these type of firms. Etc etc


I have that same Armoury x Real McCoy t shirt and find it a touch long to wear untucked. Seems to work for you though.


Hi SImn, did you get a medium size / 38 from RMCoys for your t shirt? I usually have the same length problem..M


Try the lightweight t shirts from Asket. I have the same issue. 5’9”, most t shirts are too long. They make shirts in three different lengths.


Hi Simon
Not sure about your comments with regards to looking out of place within reason. I have never wanted to ‘fit’ with what others are wearing or what is expected to be worn in holidays situations as in this post. Being part of the flock is all too common these days and, as standards have plummeted, even less attractive to me. Agreed you cannot wear a suit to the playground, as you quite rightly say but, being a tad overdressed but in a casual way gives one confidence, attracts comments and, sets one apart from all the others. Lets be honest, we all read your posts because they are all about being dressed up in one way or another. So proper shorts (so hard to find these days), with or without leather belt, linen shirts, chambray or knitted shirt/top (tucked in according to style), panama or simple straw hat, sunglasses and simple leather or espadrilles, always looks relaxed but stylish. Base ball hats are a no-no for sure (they are called base-ball for a reason)
An in depth post on shorts would be great and where to get them (1950’s and 1960’s Esquire style for example or even bespoke)?


Not sure anyone, including Simon and definitely me, can speak for every reader and their motives for reading this blog. Certainly from a personal perspective I dont think I really want to “dress up” and definitely don’t want to “stand out”… that all sounds far too much like trying to be a peacock for my tastes.

Personally I want short cut advice on dressing appropriately rather than up, how to combine things, learn from someone else’s mistakes who has much more time and budget to experiment than I. Many things recommended will be too expensive, too long or too slim for my wallet and body but it can occasionally be transposed to other options.

I do still attract the occasional comment, but its normally from like minded people who also appreciate a good linen etc. When its the random person on the street I start to think I’ve pushed things too far and need to dial it back. Things are different if a conversation moves on to clothes but then I’d rather my knowledge (much learnt from this blog) rather than my suit is what impresses.


Very interesting post, Simon! I’ve been thinking for a while that the terms ‘casual’, ‘smart casual’ etc are outdated and have serious 90s undertones. For me chinos and a shirt is quite casual but then how would I describe a t shirt and shorts? Ie these terms are quite relative for each person using them but somehow they do not convey the fact that there is no absolute standard of what casual actually means. Therefore, I think people should drop casual and focus on what is elegant (and my suspicion is that most people reading PS above all want to be elegant and not smart or casual or whatever). Somehow we too often think that ‘dressing up’ will immediately make us look good (not true, think of trump in white tie) whereas the picture of you in chinos, sweater and neckerchief is very elegant.

Also, I think a brief outline of what reviews we should anticipate would be helpful (indeed I would like to mention that reviews and the introduction of new brands, especially if they aren’t well known, are fantastic parts of your website)


You sir are a genius! “ the biggest risk of middle aged men in the Summer: looking like a schoolboy.” Brilliant and very true! Thanks for another outstanding article with sage advice.


Love your red MAGA hat.


Except he hasn’t ruined them for Kanye


“As long-term fans of menswear will tell you, half the pleasure of being well dressed is separating these kind of occasions deliberately, and creating a little structure. ”

Very much agree with this. When you dress for the occasion, seasons seem more seasonal, festivities seem more festive, celebrations seem more celebratory, vacations seem more vacation-y, etc. In short, dressing for the occasion makes every occasion feel more precious and unique.


Mr. Tom Ford’s advice on shorts is, as always, spot on: no shorts in the city. If people would follow that wise counsel they’d be so much better off.


I really don’t get this “no shorts in the city” thing. Is it a maxim belonging with the “no brown in town” school of thought or merely the personal preference of some people regarded as influential? Yes, I can see the point about shorts not being worn in a professional environment, more formally styled restaurants and out of respect at some social functions but that applies just as much anywhere, urban or otherwise. Those PS shorts with a well fitted polo or linen shirt with some loafers etc are surely acceptable in a city? I assume, Simon you won’t object to this too much given your publicity shots are taken outside coffee shops, parks etc?


Simon, if I may challenge you just a bit on Mr. Ford’s rule being a just a suggestion. I’ve been following him for many years and he’s been adamant, best I can tell, on the issue of shorts. He’s said that really shorts were only appropriate at the resort,beach, tennis court, or gym and never in the city. And he’s been very clear that shorts are just not a good look in general on men. Now I consider Tom Ford one of the best dressed men on the planet so, I take his advice seriously and I agree completely with his position on shorts. If there’s one piece of Summer clothing that can make a grown man look like a schoolboy it’s shorts; and in the case of cargo shorts, a hideous one!


I happened to catch sight of somebody in shorts this week, on a very rainy Wednesday, in the Square Mile of all places. Although there was nothing particularly slovenly about the person’s appearance (there were plenty of other people walking around in ill-fitting trousers and white shirts who looked less well put together than this guy), the outfit was very noticeable given the setting and the weather, arguably not in a good way. I suppose it goes back to the point above about appropriateness – outside of the suburbs, in a business environment, shorts will be an incongruous look on most occasions. Combined with the sort of weather London experiences in the summer – where you often need to be armed with a raincoat and umbrella in August – the bizarreness of the choice is exacerbated.

Peter K

Simon a similar post on how to wear jeans would be helpful. Where I live (Canada) this is by far the most common thing men wear casually. Often matched with a t shirt and hoodie. Do you have some thoughts on wearing jeans in quite casual settings? I prefer to wear them with a henley or sweater in the cooler months but struggle with pairing them to a shirt in the warmer months.


Interesting article – as always. Good also to see you relaxing and away. The aspects raised about casual wear are valid but as a counterpoint I raise the following: that holidays are exactly that – a break away from the everyday – the mental, as well as physical; respite being derived from the suspension, albeit temporarily, from the repeated, every day strains that we are placed under. As such, the regularly be-suited may, with joy, abandon the structures and strictures of formal dress with a creative (read random) approach including tan brogues. That being said the Japanese jacket is a winner. Have a great summer!


Simon : what’s your take on golf attire for such summer activities? I find that a nice golf shirt and shorts, and maybe ball cap, can present a smart appearance while still keeping cool. My local climate can be quite hot.

I dropped cargo shorts when I realized how many dad’s dress like their 6 year old sons.


John Smedley polo shirts are not suitable for golf as they soak up sweat. It’s only in the last decade or so that golf brands have switched to awful synthetic materials that irritate my skin. Legendary players like Palmer, Nicklaus and Ballesteros played great golf in traditional cotton polos.

I still wear my old Ashworth polos that were made in the USA in a fantastic thick and soft cotton. They were bought 30 years ago and still look like new after being almost washed every week in the warmer months. I also wear Sunspel’s pique polos, thankfully back to the lighter weight cotton in a wider choice of colours.


Take a look at the polo models made by Sunspel, particularly the Riviera, as an alternative to the atrocious modern golf shirt. They’re beautifully designed, very well made, and comfortable.


Bless you Tony! You’re comment about fathers looking like their six year old sons is priceless!


Nothing too offensive here Simon albeit, the ‘kendogi’ is a bit grasshopper for me. Personally I’d have gone for a nice linen overshirt. Also, I don’t like trainers on the beach but there again, I don’t like trainers anywhere other than for sports.
Nice to see clothes more in action. What would also be interesting is to see the whole trip from a-z. Starting with planning the wardrobe, the actual packing, the airport, each holiday event, the return and a post analysis of what was and wasn’t worn. I appreciate this may prove intrusive and might mean you have to take Jamie with you but it would make for innovative flaneuring.
I’ve got to the stage whereby I’m so ruthless on packing that I leave out that vital item. Whereas in previous incarnations I’d have taken everything but the kitchen sink and brought half of it back unworn.
Decisions…. decisions, can a flaneur ever truly get it right ?


For me, the opportunity is to select the items for the itinerary, pack them and follow the performance of the selection throughout the trip and then to review the selection at the end – if that makes sense ?


Two points from me…
No shorts in the city… Yes it is a bit trite but I think valuable. cities (as simon points out) are formal, shorts arent (parks etc excluded). More importantly they are bleeding filthy!

2 – trainers with invisible socks are great for walking, around the house etc. For the beach / boat though not so good. I have a pair of woven leather juttis that are just the one.


My wife and I are a few weeks away from a 2 week vacation in Naples and the Amalfi coast. In keeping with our philosophy of not standing out as obvious tourists and travelling with only carry-on luggage my wardrobe will consist of the following. Navy,black,and light beige cotton trousers. A navy bathing suit which will also double as shorts for informal beach wear. A selection of pale blue and white long sleeve linen shirts in addition to several cotton polos in navy and white. For footwear one pair each of navy and black suede slip-on sneakers although I will wear a pair of black Clark’s chukkas for travel. In addition a light tobacco suede blouson for travel pockets and cool nights completes the selection. A beige Panama hat and perhaps a light grey fine wool sweater. That’s about it except for socks and underwear and it all fits neatly into a carry-on.


I hope there weren’t any arguments with the missus about her photography skills (I take it you got her to do the snaps of you, Simon?) One thing that no one has commented on is vacation washability – the best holiday garments should be lightweight and easycare, especially if a washing machine isn’t available. We all have favourite holiday garments that take a hammering on the beach but can easily be washed out in a sink with travel wash. Finding something casual with a bit of style compared to everyone else’s T shirts and shorts that is also easily cleaned is not always a simple task.


On balance, I agree with VSF and Anonymous on wearing shorts in the city: basically don’t, particularly when there are other alternatives. I’ve seen many wives of friends of mine literally cringe when their husbands wear shorts at Summer events in town. In fact, the women will often whisper in my ear asking me to suggest to their husbands that shorts aren’t the best choice. Needless to say, I politely decline those requests.

Owen Eather

Well, I suppose an Englishman would need to endlessly rattle on about ” shorts or no shorts” – starve the lizzards! Now, I live in Sydney, one of the most Cosmopolitan, racy and plugged in cities anywhere. We also have 22 surfing beaches within an hour’s drive from the Opera House. Casual we do as an instinct, not requiring a thesis to dress for a back yard barbeque or beach party. The very practical demands of Surfing – both board and body, sailing, Rugby football ( both codes), and hundreds other sports engaged in year round tend to drive casual garb. World surfwear brands, like Quicksilver, are favorite selections – rugged, practical comfort being built in. Of course you don’t wear board shorts to a board meeting ( deliberate and creaky pun), but that is bloody obvious. Now. I have three tailors, two in HK and an immigrant Greek, who do what they’re told and, like me, admire British style and suitings – the latter woven from Austrslia’s matchless Merino fine wool. However, the suits stay in the wardrobe when relaxation beckons. I don’t want to have to think too hard on clothing for doing not much. Ease up fellows, who cares what you wear when its fun time.


This is an interesting piece and underlines how fine the balance is between looking terrible and looking OK-to-good in the hot weather. I’m pushing 60, which represents a further brake on what works and what does not. I tend to work within the following age-inflected guidelines, with decent results :
1. No trainers unless they’re very low profile and canvas. Ideally not white – I’ve never seen white sneakers look good on oul’ fellas. Espadrilles are great especially in the extremely hot and humid weather. They work like magic to keep feet comfy and the esparto rope sole simply feels great on your feet. I feel like I’m on vacation when I wear them, even when I’m not.
2. No baseball caps. They’re just terrible on old people in almost all cases. A Cuban cap is almost the same, yet the small difference in shape makes it look less like you’ve given up. But really, a brimmed hat works best – not floppy or ultra wide-brimmed.
3. Shorts are a danger zone. Men’s legs seldom look good, and older mens’ legs….well….let’s just say that shorts can work by only choosing shorts that are not baggy at their lowest point and that stop at the top of the knee or slightly lower. No pleats, no cargo shorts. Shorts are the one garment that the ubiquitous “2% elastane” actually complements in holding in any threat of bagginess. Of course they mustn’t be figure-hugging either.
4. Top. T-shirts are fine as long as there’s no writing on them and they’re not sagging. Good cotton (pima is worth splashing out for). Breton striped shirts are a little hackneyed but they really do look excellent on men of all ages. At my age it’s best to avoid the traditional boat neckline and go for one that is a standard crewneck to avoid displaying a scrawny neck. Linen or linen blend shirts are excellent too, although I tend to avoid short-sleeved ones. Polo shirts are fine if they’ve no logo on them, camp collar shirts are à la mode and justifiably so. Again, they need have no loud print or writing, just a plain and well-made one will do nicely (Uniqlo does a great one using modal fabric which performs very well).


This is brilliant and very sound and wise advice indeed. Your comments on shorts, in particular, are so true.

Peter Erikson

So a couple of thoughts here guys.

What does in the city mean? City of London? Palermo? Palma de Mallorca? Paris? Manhatten? Milan? Madrid?

So the “no shorts” rule gets exposed as nonsense.

Smart casual? Who cares? Why fixate on something that you can’t proscribe? Am I smart casual, quite smart causal, smartish casual, very smart casual, overly casual? There is no answer to this. You may go to a casualish event and be spot on, over or under; until you get there, you will never know, because you won’t know in advance what everybody else is going to be wearing!! You risk being called a t+sser for being over dressed, or a t+sser for being underdressed. Nothing Simon tells you will help you avoid this.

And if you go to a “do” after work and you’re wearing a suit and take the coat off, and others are wearing shorts, or chinos, or linen I don’t know what, does it make you a style car crash? Of course not.

Simon, I think you re making life harder for people, rather than easier.

Stick to tailoring; that is where you have amassed some expertise over time.

You posted a picture of yourself on the holiday snaps post wearing long rousers with no shoes; that sums up perfectly how much you still need to learn before you can start to counsel others.

Peter Erikson

Well Simon let’s agree to disagree.

I had dinner in one of NYC’s most celebrated steakhouses the other Sunday evening. I would estimate half the male guests were wearing shorts; well cut, Ferragamo loafers, polo shorts etc. The ladies were dressed to the nines.

Nothing looked out of place.

And by the way perhaps the guy wearing brogues on your plane didn’t have anything else to wear. Don’t be so judgmental.


So the women were dressed to the nines, but half the men were wearing shorts and nothing looked out of place? You’re kidding us, right? What in the world has happened to New York? It doesn’t matter what kind of loafers the guys were wearing or that the shorts were well cut. Wearing shorts to dinner at a very nice restaurant in one of the greatest and most fashionable cities in the world is a stunning sartorial faux pas and so inappropriate, unbelievable. My wife would never have let me walk out of the house looking like that, it’s childish.


Does your wife tell you what you can and can’t wear VSF? My sympathy.


No, never actually. However, one of the many great things about a good wife is that she always looks after her husband’s best interest. So hopefully your wife, if you have one, would think enough of you to do the same and suggest that wearing shorts to dinner was ill advised.


Simon, it’s amazing to me the mental gymnastics that people will go through in an attempt to justify their poor clothing choices or bad taste. I mean trying to cast doubt on what a city is or feigning confusion about appropriate dress for a certain event for example is ridiculous. Grown men, particularly PS readers, should know these fundamentals and accept them.
By the way, trolling you on your own website is bad form, very bad form. You’re most gracious and willing to engage readers who disagree, as I can attest, with you and start a dialogue. This is a wonderful thing and how we learn and improve our knowledge. Personally I have benefited immensely from the back and forth discussions, as have other readers I’m sure. There’s a big difference however, between a respectful disagreement and an ad hominem attack. Please forgive me if I’ve spoken out of turn, but I think it’s important to point out.


Simon, I have to concur with VSF on this trolling matter. Quite frankly this type of behavior is rude, boorish and completely unnecessary. Vigorous discussion and differences of opinion will happen in this increasingly sophisticated and knowledgeable group and that’s great. However, comments of a personal nature should not occur and are highly inappropriate.

Mark Davies

In the interests of balance, I think Simon does a pretty good job in providing advice and guidance to those who seek it.

It was particularly evident during the early years of PS, when it was about bespoke tailoring and those who provided it.

However, PS has kind of morphed into a site where Simon has become an expert on anything related to style, and some of us do wonder where this authority emanates from.

The result is that anybody who seeks to present an alternative viewpoint risks being a bit dismissed and certainly having their own points of view slightly rubbished.

What we should be doing is sharing experience, successes, failures. What we should not be doing is assuming that Simon sets the benchmark against which we can or should judge ourselves.

Wearing long trousers without shoes, at home or not, is never going to be a good look, so why post a picture of it? Equally, wearing black shoes with cream/white and a blue shirt top is a disaster, and should be called out as such.

PS is great for reference, but don’t take it as gospel, because it isn’t.

No such thing exists.

Mark Davies

Hello Simon. Apologies, I should have been clearer on my point about black shoes with your outfit.
I suppose my view is that black is the most formal of colours for a shoe, and thus looks out of place against this very informal combination. For me, any shade of brown suede, dark blue leather or suede, or even a red leather or suede driving shoe would have made a much more appropriate match.

Calvn Man

In all of Simon’s articles I have read here on PS, I think Simon has always advised on dressing for the occasion/situation, your own body shape and comfort – and not dressing relative to anyone else. I would like to think that most readers of PS understand that and appreciate the advice.

Sam Tucker

I agree with most of your points, but there are a few things I’d challenge. The first is pleated shorts. Pleats vs. no pleats is I think really an issue of your body type. Men with small hips are probably better off with flat fronts, but men like me with big hips benefit from pleats. There are also advantages in terms of comfort. These look quite nice (at least to my eye).
comment image

Personally, I’ve found I usually prefer rolled-up chinos to shorts. If your chinos have turn ups (mine do, I always prefer that my trousers have them) you can easily roll them up to whatever height you’d like, and the resulting look is even more relaxed looking than shorts.

The only other thing I really disagree with is the printed camp shirts. I’d avoid the really busy prints, but a simpler print against a plain background can look nice.

Calvin Man

Having just returned from Rome, where it was beautifully (and sometimes uncomfortably) hot, dressing appropriately needed some thought. Not only are our Italian friends always immaculately attired but many places (e.g. the Vatican) required a level of conservative clothing. In the end, I settled for shirt (sleeves rolled up) and linen trousers or smart, cotton shorts cut to 2-3 cm above the knee, which seemed to work well and didn’t get any rude looks from the locals. I will add that my shorts are all old, slim-fit chinos that I cut down to given them another lease of life. A panama hat would have completed the look but packing a baseball cap (not a MAGA one!) was far easier.

I totally agree with Simon that below-the-knee or baggy, “cargo-style” shorts seldom look good on anyone.


I really like you choice of the linen pants and shirt with rolled up sleeves, very nice. However, I’d suggest that shorts was not a good choice with other more appropriate, and comfortable, choices available. So, cotton pants, or a cotton and silk blend, along with a Sunspel or John Smedley polo shirt would have worked very well and been comfortable, even with the heat. The subtitle of this piece “Or, No Shorts in the City” is wise advice, but often not taken. One PS commentator on this thread referred to shorts as a danger zone and that men seldom look good in them and he’s right.


The well travelled Alan Whicker regularly wore a blazer. “You can wear it on the beach or in the Governor’s palace and not look out of place.” …

Sam Tucker

I’d be too worried about getting sand or saltwater on my blazer to wear it to the beach.


I’m sure Alan Whicker would have placed it loosely over the shoulders of one of his bikini-clad lovelies if it were necessary to do so, Simon. It would then look just right.


Hi Simon, You may be right, though Scarborough does get chilly mind!!

Michael K

Hello Simon,

Writing to let you and others know which PS-reviewed brands have rescued my hiking holidays from the tyranny of heavily branded chain store outdoor wear.

For this year’s holiday we needed ten days of clothes that could stand 30 degree heat during the day, and 1 or 2 degrees on a cold mountain evening at 3500 metres. Boots and trekking socks apart, almost everything had to do double duty as town clothes and be presentable enough to come straight off a trail and sit down for lunch or an afternoon glass of wine in a restaurant that didn’t cater solely to backpackers.

Six brands that I’ve tried on the basis of Permanent Style reviews and recommendations made up the vast majority of what I wore: Sunspel, Zimmerli, Inis Meáin, Drake’s, Baudoin and Lange, and PS itself. A Sunspel polo will fold down to a size that can comfortably stored in a waterproof plastic bag at the bottom of a pack for an emergency. This year’s Sunspel camp collar holiday shirts are beautifully made, and while not elegantly or closely cut, they are airy enough to hike fifteen miles in and still smart enough to put on over a pair of Drake’s khaki trousers with B&L sagans on the feet and a grey-linen half-zip sweater from Inis Meáin for a nice supper out. And one can substitute a pair of jeans for the chinos just as easily, for lunch in the village square. Meanwhile, Zimmerli is the ultimate base layer — it stays warm in the cold, it wicks better than most ‘performance’ fabrics, and it cleans up with a bit of gentle soap in the sink of the hotel. Zimmerli pants for everything then, and Zimmerli vests as a hiking base layer under an Inis Meáin crewneck wool-linen blend that I bought four years ago, decided was too casual for anything but the outdoors, and that has proved an indestructible hiking companion — the combination of linen and wool breathes wonderfully when it’s hot and sunny, keeps one warm as the temperature drops, and most importantly (and unlike too many mass produced ’technical’ top layers) both dries out every night over three or four consecutive days of hiking without needing a wash *and* without getting noticeably smelly. And then there’s the PS cashmere watch cap, which made all the difference between going inside and sitting on the veranda watching the sky darken after the sun set and the wind picked up. (And I still use a JPLC brown leather Aviator as my day bag/man purse, and La Portegna slippers for the long-haul flights, two other PS articles doing their thing…).

What’s missing from this string of PS brand successes? Hiking boots are, I hope, never going to be a bespoke fashion, as the Italian designer brand versions that were everywhere in the magazines a couple of years ago looked absurd, but that said, mass production of hiking boots in China has been a disaster for both performance and durability — brands I wore in the 80s and 90s are now junk. I now rely on Asolo, who still have one line that they claim is manufactured in Italy (I suspect Romania) but that is heavy, consistent, and stops one breaking an ankle with proper resoling. I doubt they can be bettered, but I am sure some enterprising high quality brand could take on and produce a sun hat that performed as it must if it’s to be useful — blown into a thorn patch, crushed under stones, exposed to merciless sun, and washable without stains no matter how much one sweats into it. My wife and I both have ancient Tilley hats that we owned long before we met each other. They are ugly beyond belief, but they have never stained or become misshapen, which means nothing has yet bettered them; for better and for worse. Finally, a pair of hiking trousers must surely be the biggest gap in a good workwear/outdoor wear brand’s portfolio. They must be robust enough not to rip at the seams from unexpected movement, trips, slides, stumbles etc., while the fabric has to resist tearing when snagged in the above circumstances, and ideally, there should be a way to elegantly roll the trouser leg to just below the knee for extremely hot weather and/or shallow fords. What they should not have is the bane of the typical mass-market version — several dozen meaningless pockets confected as a silly fantasy of mid-century photographers in warzones, integral belts that insist on either cutting into one’s midriff or dangling uselessly unfastened, velcro (anywhere, of any sort — it simply collects wool from one’s sweater or hiking socks), or zip-off trouser legs. And the cut should be non-tragic. I’ve yet to find any that meet all the right criteria.

Regardless, thanks very much for introducing me and others to brands that look good while performing well, amidst the sea of holidaying men dressed head to toe in identikit branded leisurewear.

Rich Murley

I enjoyed reading this.

What do you wear to fly? I like jackets because of the pockets for passports/tickets etc. but worry they can look a bit formal but then don’t know what else is best, so I tend fall back on a linen jacket and jeans (I always find aircraft cabins cold at least).

I like the comment about avoiding looking like a schoolboy.

I’d love to know a stylish, practical way of dressing for flying these days.


What’s wrong with bermudas? I was wearing shorts (other than swimwear) for the first time in many years and thought a bermuda would be more elegant.


Shorts are a challenging look under the best of circumstances. So, as Simon has advised, proper fit is essential for the man not to look like a school boy or just plain goofy. If shorts go below the knee that is a seriously goofy look. You might as well be wearing Capri pants so, best to avoid that.


Influence or inspiration, accepting or rejecting a certain look is very personal. I received my own kendogi last night, so thankyou for you’re inspiration Simon…..


Found a taste of paradise in the south of Portugal, no?
All in all a great scenario for staging relaxed clothing.
Please return!


hi simon can i ask if your alden loafers in the picture above (with the shorts) are a snuff or dark brown? They seem a very nice shade of mid brown that is not too light and not too dark – something i find useful


‘It’s possible to be overdressed in this way, too’.
If such an outfit which you are wearing or for example an outfit like a shirt/polo with linen trouser and espadrilles can seem overdressed then what does the average crowd wear?