Holiday snaps 2022: Illustrating versatile packing

Wednesday, August 17th 2022
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In recent weeks you may have noticed comments have not been published quite as quickly as normal. That’s because I’ve been on holiday - in the north of Portugal, where my wife’s family is from. 

It’s a beautiful part of the world, quiet and lush, and we usually rent a house in the countryside for a couple of weeks. There are occasional visits to Porto or Braga, or shorter trips at the beginning and end of the holiday, but otherwise it’s family days of swimming pool, river beach, reading and games.

Most years, I write a ‘holiday snaps’ post on PS with some very off-hand pics of what I wore or took away. You can see those by searching for that term. 

This year, it was particularly relevant because readers had asked for illustrations of the holiday capsule wardrobe I wrote about at the end of July. 

I made it clear in that article how restrictive my packing is - because we’re a family of five, and on reflection because we have a two-year-old who still comes with vastly disproportionate baggage. 

Pretty much everything has to work with everything. Every top with every trouser, every trouser with every shoe. And the clothes need to cater for city, pool and country walk. 

Have a read of that article if you want to read about how I deal with those requirements - and keep some interest in the clothes themselves. 

Here I’m showing a few of them in the wild, such as the biscuit linen trousers above, picked because they work with both dark tops like the indigo rayon shirt here, as well as white shirts or T-shirts.

Out of shot are my black-dyed Alden LHS loafers, the smartest option of the three pairs of shoes I took, and still the most comfortable non-trainer I own, so great for travel. 

Above, another dark top - my black Perro polo - worn with olive-linen trousers. The olive also works with the white or very dark tops, and is particularly nice with black. 

They’re an old pair from Informale, as I didn’t have time to get a pair from The Anthology before I went. I prefer the latter, as they don’t have the double pleats that give a rather baggy effect here, and they’re better made overall. 

The espadrilles are black, from Diego’s. It would be a little more interesting to have shoes in a different colour to the top, but these are the kind of little compromises required with a small suitcase. The black shoes go with everything. 

Another little rule of thumb I find practical, is that wearing one long and one short is an easy way to avoid the danger men often have in hot weather, of looking a bit like a child. 

You see it all the time, at least where I live. The wife is in a flowing linen dress or a chic pair of shorts with a Breton top, and the husband is wearing an old polo with slightly too-tight shorts. 

Now, chances are she spends far more time thinking about clothes than he does, and that’s the major reason for the difference.

But often all it would take to avoid that look would be a long item on the top or bottom - a pair of casual linen trousers with the polo, or a casual linen shirt with the shorts. It's not the only way by any means - shorts and a polo can look good - but it's often the easiest.

In the pic above (shot by my 11-year-old as she also relentlessly mocks me for having to do so) I think the linen shirt from Anderson & Sheppard makes the look rather more adult than a T-shirt. 

And it doesn’t have to be an expensive shirt at all, any loose-fitting and relaxed linen will do, just as long as it doesn’t look like office wear. Chambray or denim works well too. 

Which is not to say I don’t wear T-shirts. A good-weight T-shirt, like the PS Tapered Tee above, is a practical thing for more rugged activities, such as going for a walk through the woods, or renting a kayak and paddling down the river. 

Or in this case, trying to make the kids laugh by mimicking the cardboard cut-out at the local Intermarché. Nothing but Dad jokes, all summer long. 

Those shorts, by the way, are a nice pair from RRL I bought before the trip and am trying out. They’re in a strong right-hand twill, the same material I think as the ‘Field’ chinos that reader Cedric recommended in his recent profile.

What else?

My swimming trunks are from Aspesi but I’m not sure I can recommend them. The blue colour has quickly faded to a slightly unexpected mauve (above). 

My old Bate’s straw (below) looks better and better as it gets more beaten up. The two-year-old actually managed to step on it during the holiday, and put this hole in the top. It’s such a nice example of wear (and tear) that it almost looks fake.

And my Meyrowitz sunglasses continue to be one of the most versatile things I’ve bought recently - the Californian model in ‘amber mottle’ acetate (below). 

They’re very expensive, but so far I’ve managed to avoiding losing or damaging any of my Meyrowitz pairs (I have three) so as long as that lasts, it’s worth it. I just make sure to keep them in at least a soft case. 

That green alligator case is actually something else I’ve had for years and managed not to lose. It’s brought me such pleasure, with almost daily use during the summer. 

Searching for the original post on PS, I realise I’ve had it over 10 years. It’s hard to question the value of something you're enjoyed for that long. 

Here’s hoping you’ve all managed to get away this summer, and take some sartorial pleasures with you. 

If you have any tips yourself on packing for such trips, or recommendations for clothes that have worked out especially well, I’m sure readers would be as pleased as ever to read about them in the comments. 

Now I can't wait for autumn - with coats, scarves and hats galore. 

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Hi Simon, we just got back from a few weeks by the sea in Corsica. Even though I always pack a lot more, I find the only clothes on holiday I ever use are long sleeve linen shirts, linen trousers and swim shorts. Linen shirt and trousers in the afternoon and evening after the sea, then reuse the shirt and throw on swim trunks the next day to go to the sea. Shoes are espadrilles or Sebago boat shoes.

As an alternative to Aspesi, I like Fedeli Madeira swim trunks. They have lots of colors and also nice patterns, aren’t too long, and dry quickly.


For an autumn/winter trip, I would recommend a wool pakol. Mine is used for headwear, keeping my wallet under, cushion, neck rest for flying and occasionally a substitute cricket ball.

Rupesh Bhindi

Hi Simon,
Which fabric mill is the cream or oatmeal linen trousers made from worn with your brown linen overshirt?

Erik P

My holiday wear were sport shorts and neoprene socks – the merino t-shirts look good anywhere though. Excellent material for both long hours in the kayak and everyday wear on shore, even on hot days. Helps downsizing my wardrobe when they are so versatile

Eric Twardzik

I bought the same RRL shorts two summers ago, and have worn them near daily for the past two seasons. This summer I bought a second pair just to rotate them and save the first from wearing out too soon. I find that the the flap pockets at the rear and the military-style fabric add just enough interest to differentiate them from the million pairs of anonymous khaki shorts worn on the American East Coast each summer.

Prince Florizel of Bohemia

Nice article and pictures. May I ask you what part of bottoms you take for holidays is machine washable? I might be especially messy, however, on holidays, when I spent a lot of time outdoors, having easily washable clothing is part of the practicality of packing. And I don’t want to bother with dry cleaning on holydas, let alone not knowing how reliable the local service is. Thank you.


Hi Simon,
I hope you are enjoying or have enjoyed your holiday.
I couldn’t agree more on shorts with shorts especially shirts- it just looks funny and not stylish. The example you mention is very common
I think a semi fitted polo or t-shirt and looser fitting shorts are ok as you demonstrate the latter in your picture. Fit is important even on casual clothes.
Other than a polo I prefer a linen point collar or cotton (plain or well washed madras) with sleeves casually rolled with shorts. It just seems to balance out.
Your advice is good as with any capsule wardrobe the optimum interplay of items is critical. Ideally if applied to one’s whole wardrobe we’d waste and spend less, but that’s easier said than done and I’d like to say I do it but sadly not!
Not sure if you have ever written a about packing? Which may be of interest; eg rolling vs folding?
li you, I’m looking forward to autumnal and winter dressing – but not the fuel bills! Now there’s an idea – stylish and warm at home!
All the best.


Thanks for another insightful article Simon. Your reflections on footwear were of particular interest.

I’ve been thinking through footwear options for my next hot weather trip and have noticed an increasing number of deck shoe / loafer hybrids on the market. Walking around Edinburgh city centre this afternoon (in the most fantastic weather) I noticed Loake, Church’s and R&B were all offering a rubber soled (often natural in tone) suede loafer which feels very much like a crossover shoe, designed to span the breadth of day and evening activities you might undertake over a holiday break. Perhaps the best example I have seen is the Sagan Stride. Do you feel those shoes offer a good compromise or are they perhaps too casual for smarter (although still relatively relaxed) evening wear.

Thanks and hope you all enjoyed Portugal. It sounds like a great way to pass a few weeks. Scott


I agree wholeheartedly with your long/short recommendation. However, I would suggest that the long should always be the bottom. Save the shorts for the beach, tennis court, or gym as advised by Mr. Tom Ford. Shorts don’t flatter men, but men stubbornly still insist on wearing them. So leave the shorts for school boys and dress for the Summer like an adult.


Of course the practical side is an understandable exception, particularly concerning young children. By the way, I really like the hat that your two year old daughter stepped on. The hole adds character and a story so keep it as long as possible.


Lovely article Simon, thanks for sharing the photos with us.

Those RRL shorts, mind if I ask, are you wearing a 32?

I’m loathe to spend substantial amounts (relative, £100+) on shorts, simply because of the weather where I live, even in the summer ‘shorts weather’ is limited to a matter of weeks at best.

Still, I was caught out this week past as a heat wave rolled in. I was actually eyeing up a RRL pair similar to these, but navy and garment dyed. Think they might prove a solid long-term investment. Leg length and rise looks perfect too.


Cheers Simon. Yes, I think you’re right, not quite this same tougher fabric by the looks of it.


At a guess as these are the ones I saw after reading this article


Hi Simon,
We came just back from a journey through Portugal starting in Porto over Lisbon to Sagres. Maybe even more than you I had to consider that nearly half of our vacation was in cities and the rest in the countryside / on various beaches.
What worked well for me were beige and navy linen chinos from Luca Faloni (with a hidden drawstring), white / cream and navy poloshirts in cotton-pique and linen, white and navy t-shirts, a white and a pink linen shirt also from Luca Faloni, a beige and navy linen baseballcap, a stone/beige linen crewneck and a navy cotton crewneck in cotton from John Smedley.
The shoes I took were white canvas sneakers, beige and navy espandrilles and unlined brown leather loafers.
This allowed me to vary my combinations in a way that I could wear dark on top and light as trousers and vice versa. Your previous post “what to pack for summer vacation” was an extremely good guideline when I started packing.


A PS: As swimming shorts I can recommend Mr. Marvis. I have had two pairs now for the second year and they hold up well.

R Abbott

Simon, I’ve noticed in recent posts that when you wear casual shoes, they tend to be black rather than brown. E.g, the black sagans on the trip to Florence and the Black Aldens and Espadrilles in this post. Any reason for that? Do you think that black gives you a different look, or were you just in the mood to wear black rather than brown? I’m in the habit of wearing brown but looks like in many situations (e.g., olive trousers linen trousers and white shirt) you could go either way .


Thanks Simon, interesting point that the shoes in different color than the top would look better. I always thought the opposite. You think dark brown would have been fine in this outfit (black top)?
p.s the olive ps overshirt would also fit perfectly in the last outfit, i used recently this combination 🙂


Big family—how lovely!


Honest post.
Long sleeved linen shirts that are rolled up +1
Tshirt/polo – no bueno for us tall guys unless covering them in a overshirt. Not sure why but short sleeve doesn`t work anymore.

Caleb C.

What color linen trousers do you find the most useful? If you could only pack one sort of thing.


Now this is a vacation sideshow presentation I sitting through


What are the “black-dyed” Alden LHS? Curious what you mean by black dyed…


Wow. That’s brilliant. I’ll keep that in mind for when I inevitably destroy my snuff suede LHS some day.


Simon where did you get this wonderfull aligator case ? I know chester mox makes some great cases by the way..


Lovely article Simon thank you. Where is the straw hat from and what style is it?


Hope you had a good time, and glad you made a new friend (referring to the cardboard cut out, bad joke I know.)
Regarding swimwear I was looking into Boggi Milano or activewear brand something like Lululemon for my winter get away, not sure what would you make of those brands considering you were unhappy with Aspesi, something to look into if you haven’t already.
One thing I have noticed is in terms of style is that Portugal is big on trainers/sneakers, I think several brands are made there Uniform Standard, Oliver Sweeny (which I will admit I like the look of or not sure of the quality) and whenever I’m shopping for trainers online ,I always see the words “made in Portugal” almost as a badge of quality, so I was wondering did you go shopping for trainers or visit any manufacturers whilst you were out there during this/previous trips?


A number of higher end brands, Sunspel for example, have their knitwear, coats etc made in Portugal. What is it about Portugal?


Well it would be an interesting project to investigate this question further by discussing it with various brands that use these Portuguese plants for some of their production. If you could arrange factory tours to evaluate quality of manufacture that would be very helpful for readers.


In the vintage shirt world, I would say the the ‘best bang for the buck’ are Gant button downs made in Portugal (especially the standard fit poplins). Well worth tracking down on eBay/Vinted etc. They are very good shirts.

Tommy Mack

Just got back from Nerja on the Costa del Sol. Very hot down there as you might imagine. My holiday staples were:

– Sunspel Rivera polos, mainly dark colours though I also have a white one (can’t recommend them enough – the perfect fit and collar for me as well as being extremely light in the heat)
– Luca Falloni linen trousers. Again, effortlessly light to wear and a perfect fit for me (I’m a small, slight guy), fitted without being tight. I’ve had cheaper linen-cotton trousers in the past which were bordering on skinny, negating any of the loose airiness you need from linen. I went for the sand colour as the most versatile. If I’ve a criticism it’s that they’re perhaps a shade too light to wear with white. I’ll probably pick up an olive pair when I’m next in Piccadilly.
– Navy canvas shoes: fine round town and smart enough for alfresco dining. As I’ve mentioned before my wife sadly hates my chocolate suede loafers so they stayed at home!

I also took an old pair of stone chinos for eating out in slightly fancier restaurants (being almost white, these are a bit too dandyish for me these days and I seldom wear them in the UK but in the hot weather they go well with the dark polos) and a couple of pairs of tailored shorts.

Interestingly, one of the pairs of shorts is a black pair I bought on impulse and slightly regretted because, well…black shorts? But I found they look good with white or a very pale grey stripe John Smedley polo I also took.

Finally, I threw in a couple of old linen-cotton shirts for the beach. I don’t tend to wear T-shirts in bright sunshine because I prefer a collar to protect my neck a bit.

Tommy Mack

Btw: you’re a braver man than me, taking your best sunglasses on the beach. I have a couple of beaten up old pairs (and a watch) I keep for just that!


Hey Simon a few observations:
1) wow the informale trouser looks messy at thr hip area! Not a good look
2) i really like the white linen shirt with the khaki shorts. Given your recent love of rayon shirts have you tried bryceland rayon shirts? They look nice tucked out over shorts but beneift from being long sleeve too

Ned Brown

Fantastic post. Love the hat.

A woman who loves to read about men's style

These outfits all look great on you, Simon. Relaxed but sophisticated. Well done!


It’s good to have constraints in your travelling wardrobe, it concentrates the mind on what is really needed & what is not. And as ever often based on the weather or activities some items are not worn. I find that freshening up linen shirts & stretching back into shape along seam lines ( if done correctly) often is enough for a casual look & makes little difference once on after a short time, I’d expect the same for some shorts & drawstring linen trousers. But Simon, how do you cope with such travelling with a straw hat ( before it was stepped on ) presumably not a hat box; I have this predicament with a newly purchased crushed straw hat; otherwise it’s a bucket hat.
p.s. I’d put those lovely sunglasses away before they too are stepped on, they’d not be so forgiving for the beaten up look;-)


Thanks for posting this! I find these articles some of the most useful. If you don’t mind, can you please let us know what belt you are wearing with black shoes (both the loafers and espadrilles)? I find my black belts too dressy for this sort of use and am in the market for something more casual.

Patrick Hanrahan

A good article and lovely country. Perhaps more relevant now than it was is the issue of sun protection on a summer holiday. Long sleeve linen is perfect, with the sleeves not rolled up! Is a turned up collar to protect the neck OK? And the weave should be dense enough to offer some SPF. A decent hat like the straw one illustrated rather then a cap, as ears need protection is good and I endorse the other comment made about longer trousers, although I find myself in shorts generally. I also was surprised to find that very fine wool trousers are more comfortable in the tropics than cotton, but look too formal unfortunately.


It’s nice to see a person in ordinary, unprofessional photos in a natural environment. I especially liked the photo with the bottle) Well, the background with the fountain was well shown …

Alan Johns

One of the main issues I have with clothes in hot weather is sun cream. I don’t want to wear a top I care about that much because I think the sun cream might stain and ruin it (over time at least). Is this just me worrying about nothing?


Hi simon i think breton striped long sleeve knit look great on women and im thinking why i dont see more men wearing them or even shops selling them. Are you aware where one can purchase them with the usual menswear details? Eg short length with ribbed knit, made of cotton or linen.

Peter Hall

Have a look here Shem

They are decent quality,but cut slim.


Dear Simon! Regarding the RRL shorts: are you still wearing them? Would you choose a size smaller in hindsight? (You said you had to take in the waist.) Do you have any other suggestions for this kind of workwear short? How do these RRL shorts (made in China, I believe) compare quality-wise to the Japanese brands like TRMcCoys, Fullcount, buzz rickson‘s etc? Thanks!


In the picture where you are wearing black polo and olive linen trousers, would swapping black espadrilles for ecru canvas trainers work? I have this outfit in mind for casual summery outings but unsure whether ecru shoes would look fine or not with an overall darker outfit


i`ve just ordered a pair of informale drawstring (i know You prefer Anthology these days, but I have yet to find out how much I will use such a pair, and informale is a bit cheeper). But I have a question about the informale You might can answer? They are cut long because you can roll the hems. But how many “layers” is normal when you roll the hems that way.
i don’t think that a 5 cm hem is what there is intended?
hope my question makes sense?


Thanks for the answer 🙂