A few years ago, I wrote a piece detailing what I packed when I travelled – focused on Naples in wam weather, but with application to colder weather too. 

However this was a ‘work’ trip for me. One where I was expected to give a certain impression, and tailoring was pretty much obligatory. 

If anyone is travelling for work or just wants to be smarter, the advice in that article still stands. But today, given I’m going on holiday soon, I though I’d do a vacation-oriented alternative.



Now, even though I’m on holiday, I don’t want to be wearing a T-shirt and shorts every day. I will take that and I do wear that, but I like more elegant clothing too much to wear it the whole time. 

Also, family holidays involve a small amount of variation in location. Although we spend most of the time in a villa with a pool, we will also usually spend a couple of days in a city too. 

And personally I think that for reasons of both style and propriety, I want to dress differently in an urban restaurant than I do at the beach. Most tourists appear to disagree with me, but I like to think it’s just because no one has explained this kindly and carefully them. Or pointed out that none of the locals are wearing board shorts and flip-flops. 

So, the conditions that variously shape my holiday wardrobe are:

  1. Heat. This is summer, and I’m travelling south. Temperatures 20 to 40 degrees celcius.
  2. Variation of formality. Beach, villa, city; playing with kids, travelling, dining.
  3. Space. We’re a family of five; no one can take too much.
  4. Style. Whenever practicable, I prefer to dress a touch more elegantly. Never in a tailored jacket, but not always in a tee either. 

With all that in mind, this is what I will be packing this summer. 




The thing that satisfies condition number four more than anything else, is wearing collars. A polo shirt or a casual shirt, rather than a T-shirt. Still, at least one T-shirt is just practical, for example when getting hot, sandy and sticky at the beach. 




The second thing that helps retain a little sartorial interest is wearing trousers rather than shorts. A loosely cut, openly woven linen trouser can be just as cool as a short, particularly with an elasticated waist. 

The colour scheme above also starts to make sense when you consider the bottoms. Pretty much every top can go with every bottom, creating a maximum number of combinations in a small suitcase. It feels kind of boring, but actually it stops me being bored.




I’m unlikely to need much here given the temperature, but will need at least one jacket-like item for travelling and going out. And at least one sweater for the late evening or early morning.

The downside of polo shirts is that knitwear often doesn’t work well over them – or at least, the thicker they are and the more structured, the less it does so. Hence why cardigans are useful.




Versatility here is of course of particular importance, given you need shoes that can be worn on the beach, loafing around, for dinner and for travelling.




Apart from the obvious, like a pair of sunglasses, a straw hat, and a pair of swimming trunks, some extras to sneak in are:

  • Vest 
    • Useful layering to deal with changing temperatures. Under a shirt, polo or sweater
  • Neckerchief
    • Cotton, tied at the neck. Again warmth, but also for sweat
  • More than one hat
    • A nice way to add variation. As well as the straw, perhaps a cap, perhaps a bucket hat. Can add colour to otherwise functional tonality
  • Short pyjamas
    • I have a set from Schostal, with a short-sleeved top and shorts. Both can do double duty as normal clothes in a pinch. (Swim shorts can do that nicely too, if not too obviously for swimming)



This is not comprehensive, excluding things like bags for travelling and the beach (also, by the way, nice ways to add some interest and colour) for example.

But the main thing is dealing with all four of those conditions, which isn’t easy when there are two kids and a baby. This basic list has proved to be a fairly successful way for me to meet them, and not lose sartorial inspiration entirely. 

Tips and experiences from others, as ever, very much appreciated. 

Other pieces that may be useful:


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Ian Skelly

Still looking for a slim tapered white chino that isn’t a bit see through! anyone got any ideas ? thanks

Gary Mitchell

Hi Ian,
Trouser, I cant help; Chino, try RRL officer chino, tapered and smart. I also wear Drakes white jeans but they are much more casual looking

Ian Skelly

Hi Gary thanks for taking the time to reply I will have a look at them, kind regards Ian


Hey Ian-
Chino is a broad term. I have several white polished cotton pairs from agjeans.com that are fab. Check out the Marshall and Graduate cut (5 pocket). Not cheap, $200 US, but half that with yearly sales.


Try Billy Reid


Jack Donnelly ivy fit 3. Perfect taper and room at the same time.

Ian A

Cordings have thicker summer unwashed chinos! I have them and satisfied for the money! Take them for tapering to an adjustment tailor!


Drakes Chinos?


This fits largely with what I’m planning to pack. What would you normally fly in?


What do you think about bringing something like the B&L Lune for the airport or around a hotel? Many thanks.


Hello Simon. Blessed Holidays with your only one wife and many childrens ? Peace be with you!


Hi Simon,

It would be great to see a follow up post covering these outfits in the various situations you desrcibe and what you felt worked. Appreciate you might not want to work on holiday but it would be a nice post.


Hi Simon, what are the espadrills pictured?


interesting, do you find they fit true to size?


I have found the sizes also varied in Diegos. Ordered my usual size Euro E44 last year and they were huge, went with the E43 this time and they are tiny.

Tommy Mack

Very nice. I’ve been thinking along very similar lines for my upcoming family holiday. Don’t understand why people wear beachwear out to dinner – where’s the sense of occasion?

My father-in-law possibly takes this too far the other way, sweating in his black Farah slacks and M&S dress shirts on the terrace but there are ways to look smart and keep cool too! One thing I’m also packing which you don’t mention is a light pair of cotton chinos as a slightly dressier alternative to my linen trousers. Sadly my wife hates my loafers so they won’t be coming with us – I’m substituting a pair of suede sliders alongside my canvas pumps.

One thing I must say I’ve struggled with is your “knitted wool cooler than knitted cotton” polo shirt tip. I get the physics behind it but I struggle, maybe more psychologically, with wearing wool in the heat. It’s something I keep meaning to try as polos are a staple of my summer wardrobe at home and abroad – I like having a collar, for style but also to protect my neck from the sun. My older polos get repurposed as beach wear once they get worn out.

On a similar note, I’m a recent covert to Sunspel’s Riviera polos and thoroughly recommend them for the hottest days of the year. The cut and collar are just right for me: flattering without being too tight and stylish while still being casual enough for “day wear”. I’ll definitely be buying some more.

Anyway, thanks for another great piece and enjoy your holiday!


Canvas pumps?

Tommy Mack

Tennis shoes really, rather than pumps per se (i.e. laces not slip ones)

Ottavio Rizzo

Usually in Southern Europe, even in the middle of the summer, a tailored jacket would be appropriate when dining out in any place fancier than a pizzeria.
It would not be required, of course, but it would not look out of place unless you were dining open air in a very humid spot.

Or is it just a question of luggage space?

[Last year, in a restaurant in the hills above Florence, my wife pointed out to me that I wasn’t the only one sporting a blue linen blazer with white shirt, grey tailored trousers and blue espadrillas: she joked about it being some sort of Milanese uniform]


If you were eating in Florence, why would your wife say you were in a Milanese uniform? Florentine perhaps, but Milan is many many miles away!

Peter Hall

I’m a fan of a Teba. Great to travel in and smart for evening. My wife swears by her white denim jacket. I always pack several vests-really handy for high humidity.

You appear to have missed out the tradition knotted hanky for headwear ,Simon.


Great set of recommendations and pretty much whatI take.
Except, I always wear Sebego Docksiders throughput the summer. They stand the rigours of sea and sand and are comfortable / robust enough for long walks. You can also wipe them down and wear them on an evening.
That way you only need one pair of shoes and trainers for sport.
Also, I don’t agree that polo shirts don’t look good under a sweater. It’s a question of which polo and which sweater.
A Sunspel Riviera in either white or navy looks great under a navy A&S cotton sweater – particularly with the collar popped (v JFK) and it’s my staple for chilly mornings or evenings.


Thank you for this very timely article, Simon! One issue I have struggled with in the summer is white shirts/tops turning yellow-ish rather quickly at the collar, particularly when sweat and sun cream are involved. Therefore, I’m not sure if your recommendations work for me. Do you have any tips on how to avoid these stains or how to get rid of them effectively?


A few years ago, I was driven mad by the yellow sunscreen stains on my favorite t-shirts, and I tried different ways of removing them. What worked for me: make a paste of baking soda and dishwashing liquid, apply generously to stain and let sit for about an hour. (Possibly a paste of baking soda and water will work just as well – not sure.) Then soak in water with vinegar, and wash as normal. This worked for me!

Certain zinc-based sunscreens don’t stain at all, but they’re hard to find and they tend to be very opaque and white, so you look like a ghost all day.

Evatt Gibson

Hi Simon, may I ask if you bring an iron for the items that require it such as trousers or shirts? Or do you iron before travelling and carefully pack?

Christopher Lee

I find every cottage I’ve stayed in within the UK has an iron available. In Italy it’s more hit or miss though I do not hesitate to request one. Hotels have them on hand too.


Thanks Simon, another interesting article. I’m interested in how long this selection will sustain you for? Do you feel there are enough combinations here to comfortably cover a fortnight-long vacation while satisfying your need for sufficient variety in what you wear. I have a bad habit of not properly planning my travel capsule and as a result often lug around far too many clothes which is an inconvenience in itself! p.s. Hope you and the family enjoy the break.

Aaron Lavack

I’d love to read a piece on dressing well while being a parent. I’ve tried to keep my standards up since they arrived (which has been harder when combined with work-from-home conditions and the extra child exposure it entails), but the sequential child-stain/wear related destruction of some of my favourite pieces makes it harder and harder for me to make myself wear them.
Are there strategies you employ? I’m the main caregiver, so have to spend all my breaks cooking, cleaning, bathing, etc – but I still try to dress respectably/enjoyably for meetings, etc.
hearing that you’ve got three kids and still make it work makes me hope there are some smart tricks I could be employing.
Some common problems: stains of all kinds everywhere, knees getting worn/stretched from crawling, knits stretched out of shape from tiny grabbing hands, seams going from parenting contortions.



Simon, I’m really looking forward to this piece. I would also be interested in some of your colleagues’ takes as well


Simon, do you have a suggestion for strong oxfords ? That sounds really interesting



Sort of off topic, but what luggage are you using these days? I think in the past I saw you had Globe Trotter, but that picture at the end looks like a Rimowa. In the market myself at the moment…


May I ask what is impractical about Globe-Trotter?

Andy Palmer

I’m a bit of a luggage geek, having spent most of my working life on a plane to somewhere. Tumi, Rimowa and GT are all great bags, but the brand I have stuck with for the last 20 or so years is Briggs and Riley. They may not have the “look” of Rimowa but they are way better in terms of durability, and are about half the price. In addition, they come with an unconditional lifetime guarantee.

LVMH bought 80% Rimowa in 2016, after Samsonite hade bought Tumi, but they haven’t increased the prices, which are pretty close to where they were 10 years ago.


Hi Simon,
Do you use both the cabin and checked in luggage from Rimowa? If you do use the larger luggage sizes from Rimowa, I was just wondering how it holds up (dents etc) when travelling when handling is likely to be quite rough.
Sorry if this question is a little off-topic. Maybe warrants a post of its own.


I’m currently on holiday and I have a similar wardrobe. I’ll add:

– Dark shorts that are easy to hand wash (I have a pair from uniqlo). With small kids these are used a lot during meals (not at restaurants) or playing with them.
– Some sort of rubber sandals (ie Birkenstock). Easy to wash and works on the beach or by the pool.

In general, aim for items that dry quickly in case you need to hand wash them.

Tommy Mack

One of my holiday essentials is sunglasses: Ray- Bans for in town, cheap old ones for the beach. I’ve lost a couple of pairs into the sea doing watersports so definitely won’t be wearing my Clubmasters for that!


curious why so much white and (probably much?) black.?


interesting. and navy instead of black wouldn’t work? I have black shoes and black polo, but I find they are last things I reach for. somehow charcoal and navy polo seems much more wearable with cream, beige and olive trousers… and somehow I suspect I’d be happier with navy espadrilles instead of black ones too!

white… white is nice, but too much trouble for me to keep clean!

but with the rest I completely agree.


re dark brown. I’d be happy to get a reasonably priced polo/knitted polo to try but anthology is a size too small for me, I’m not sure wool or cashmere is right for me, and I haven’t seen any more nice dark brown cotton ones /.(even if I would want a colhays, I’m not sure if they are not a size too small for me too, they seem quite borderline).


I’m in the markt for a white linen shirt for vacation use. Does anyone have experience with the linen Giles from Orlebar Brown?
It seems casual enough to pair with their swiming shorts to grab a drink or a snack near the beach but als formal enugh to wear to dinner with long trousers and maybe a blazer.
I’ve been looking at the offerings from A&S, Rubinacci and Drakes and they are all a little pricier (and on the formal side) and given the limited use durig most of the year I’m not quite convinced I want to spend that extra.


Hey Simon, thanks for this one. I’m not travelling any time soon but I enjoy these for future reference (and to live vicariously through anyone going on a trip of course).
On a somewhat related note, would you be interested in doing a piece on climate change and how that will affect our perception of which clothes are to be worn for what and where? Geography is of course key to so much of how we approach clothing. I know the UK is in a similar heat wave to what BC experienced last summer that really shook up our notion of how our society has been operating — for example, our lack of air conditioned spaces and how urban centres can be full of heat-reflective surfaces and don’t provide much in terms of heat shelter in summer. I think, perhaps with a guest, you could add a great perspective.


Surprised to see a black polo in the summer. I would only consider wearing it in the evening. Is it what you intend to do?

Depending on where you are going, wearing a jungle jacket might look a bit costumey. Mainly in countries with mandatory service.

You linked to the Wax Walker instead of the RRL Arran-knit.

Most Japanese brands stop at 44EU.
Do you have an alternative for the Doek for those with bigger feet (44.5-45EU)

A woman who loves to read about men's style

Simon this travel capsule wardrobe sounds chic, comfortable, and versatile. Thank you for encouraging men to avoid board shorts and flip-flops groupthink. Whenever I meet a male friend who is wearing flip-flops in a setting that is not near a body of water, I offer to buy him shoes.


Hi Simon – what size is your Rimowa suitcase and is it a good all rounder?


I’d strongly recommend sticking to carry-on luggage right now, as the lost luggage situation is out of control in Europe. On a recent trip fully half the plane’s checked bags didn’t make it past the connection. I still don’t have word of my things weeks later.


Hi, given that this is a family trip how do you plan on doing the watching for this and everything else? Or are you committing to daily hand washes?


Thank you


I thought the PS Harrington jacket by PW would be on your list of vacation outerwear. Wouldn’t it be very suitable?


hi simon i’m wondering if you will ever do a piece on the anthology linen trouser? Keen to see how you will style and wear it. I like the colours and am keen to try the style but am on the fence.


Did you find a need to size down on these? I order a size 52 and they seem rather large (relative to say your PS shorts in the same size that is).

Ben R

I was a it shocked at the lack of Friday Polos… I love my knitted polos. But I am practically living in Friday Polos these days. Often, I am rolling the sleeves during the day. And then have the sleeves down and add a blazer or Overshirt in the evenings. I find mine work just as well untucked as tucked. But I suppose a linen shirt could work fulfill the same roles while adding the button-through variety vs the other pop-overs you are bringing.


Hi Simon,

This is very useful, thank you. I’ve been taking a similar approach recently, albeit unintentionally.

I find it harder to conserve storage space with cooler weather getaways because of the heavier outerwear.

Have you adapted this structured approach for the cold?


Simon G

Great article and perfect timing! I’m headed on a small family vacation in a couple days. As I also have a baby in tow, so this really resonated and gave me a lot to mull over. Thanks!

Oh, and I second the article on dressing well while caring for young children. I just haven’t yet bitten the bullet to get my white jeans hemmed for fear of sartorial destruction.


ive got two very young kids and i have stopped wearing anything remotely fine around the house. almost no shirts and pressed trousers. only jeans, chinos, tee shirts, sweatshirts and rugby tops. nothing that needs pressing. although the current heat spell in the uk means i am wearing loads of linen drawstring trousers and loose pop-over shirts.


This could easily be a casual capsule wardrobe for people living in a tropical climate.
For someone working in a casual setting, probably this can be working attire suggestion as well.


I’d be interested to see an example of the short Schostal set if you could link / direct me to that.


Hi, do you have a really large closet or do you have some of your clothes stored away?


Hi Simon,

What hat brands would you recommend for a straw hat?
Secondly for other hat options such as wool hats would you recommend any in particular?
I was at a music festival recently and spotted somoone wearing one similar to this:
https://willandbear.com/products/andy-oak and thought it was rather nice.

I’m a fan of these slightly western influenced hats, with the narrower leather band over the broad ribbon seen on classic fedoras (perhaps from watching too much of the tv show Justified) but I struggle to envision when I would wear it. Unless i’m in a hot climate or in jeans and a white t-shirt in rural California I think I’d feel very self-conscious in a hat like the above. I’ve considered taking a leaf out of Indiana Jones’ book and purchasing a hat from Herbert Johnson but the concern then is that it veers into cosplay and frankly a lot of money for an item that might not get much wear.

Any direction would be much appreciated.


Rowan Morrison

Could you suggest (or just throw a few names for sites I could check) where the straw hats and bags for the beach might come from?

A Casual Observer

My concerns about cashmeres, linens etc are that, if you’re away for more than a week, you’re going to need to launder stuff – and hand-washing in the villa’s bathroom basin isn’t very holiday.


Yes it’s hard to beat linen when hot, yes it creases but that’s the look & it feels great. Ditto linen short as per Drakes at the moment. I also like shorts with cargo pockets which saves being cluttered with a bag or using chest shirt flap pockets which can drag the shirt a tad & cur down the circulation under the linen shirt. Something you’ve not got on your list Simon which I find best in heat are leather Roman sandals which are robust in most terrains & keep your feet cool & look great.

Ben Frankel

Excellent advice. This year I’ve travelled all navy/ indigo – with some black also- there’s a photo of Armani in dark navy T and loose cut navy shorts (just above knee) that looks terrific!
Cos have drawstring cotton loose trousers- slightly cropped length- nice for evening or travelling- black, navy and spice brown – all one needs..wash well also. Jil Sander Uniqlo fine cashmere crew neck sweatshirt in black or navy useful.
A few Indian scarves /shawls nice to travel with. Make a T more formal
Birks in rubber or the camo print v nice to wear. Spray ankles and legs for insect bites! Above packs easily to carryon flight.

Rowan Morrison

Does the shirt jacket really go that well with the polos? I’m never quite so sure myself, they seem, to me, to come from two slightly different paradigms of dressing, maybe – the polos more classic and the shacket more street/contemporary – meaning that they are slightly incongruous in a way that, say, shacket and t-shirt, or polo and Harrington, aren’t. But maybe there is something about the specific examples of these items that you have chosen, that makes them work? I don’t see the combo featured in any of the pics so it’s hard to judge.

Rowan Morrison

Ah, see, with that button-up shirt the jacket immediately makes sense, and says “workwear”. And I just don’t see the polos having the same effect – they say “sport” or “classic” to me. I only say so because I have a fair sized collection of polos myself, of different styles, and also a fair collection of overshirts/shackets. They are certainly both summer staples, however I find it hard to put them together into looks that feel congruous.

If I was making a capsule like yours, I think I would force myself to pick between either the white or black polo, and substitute the other one for another linen shirt in a different colour, which I just think would fit better with the jacket options.


Have you tried the Colhays cotton/cashmere sweaters? If so, how are they? Are they appreciably cooler/breezier than their cashmere and superfine lambswool counterparts?

Lindsay McKee

It might be interesting to do an article on how and what to pack in a good quality cabin,(carry on) bag in a hard shell,eg. Rimowa. Why do I suggest this?
With check-in luggage going missing ,big time,these days,that’s exactly what I’ll be doing shortly on my trip to London to get measured up for my bespoke commission, which leads to another dilemma…getting it home! I’ll probably wear it ,unless the airline allows a suit carrier on board the aircraft. Has anyone had this problem….what’s the best way around that?


Lindsay McKee

Thanks-I’ll check that one out.


Useful and well pondered advice as always Simon.
I realise every summer that I take too much, had I only read your post before leaving…
This summer I was also expecting a variation of temperatures, spending some time on the Atlantic coast and on the Med. But the heatwave this summer made my vest, my thin knit and my chore jacket completely obsolete. Then I have the obstination of wanting to travel with at least one jacket (I took two this time, expecting to use them in the city) and ALWAYS pack a tie as one never knows.
In the end, 4 shorts, a pair of trousers and many OCBDs were all I needed.
Hope that you had a great summer, L


Are you still using your rimowa?
What I heard the quality is lacking in recent years, but I don’t know if it’s true of course…? However, I chose a tumi carry on last year and very happy with it so far!


ok! did you buy the original or the classic cabin?
They are very stylish and I like the look, I have stayed away from the alu ones because of the weight of the cabin size and because my friends check-in bags have been quite beaten up pretty fast.

Harrison Thompson-Parkin

Hi Simon, what colour rubato long sleeve did you go with? Thanks


Does anyone have a recommendation on a cream merino polo, like this that was previously offered in the PS Shop? I see this season that cream is not offered, and the closest I can find is a silk/cashmere on Colhays.


Sorry for reviving an old discussion, but I found no newer suitable article so here come my questions:

How do you deal with sunscreen? I’m reluctant to use any of my more elegant/expensive clothing (e.g. PS merino polo) on holiday during daytime due to my need for sunscreen. I therefore default to cheaper polos (e.g. Uniqlo) and linen shirts which are somewhat ”expendable”.

Continuing along the same line, how do you carry stuff when out and about? For fear of wear I’m reluctant to use anything with shoulder straps when wearing expensive clothing. Thus again defaulting to the ”expendables” since carrying camera, water, and other heavier items by hand in a tote or similar soon gets tiring.

This all leads to the nicer summer clothing being used far less than I’d like, essentially when in the office or in the evening.

Best regards,