As I return from two summer trips – one for a week in Florence, the other a week in Naples – it seems a fitting time to run through what I pack for trips such as these. I know readers have asked about it in the past.

Of course, any travelling wardrobe is specific to the trip itself, depending heavily on the location, the purpose, and the people being met.

But Permanent Style readers will doubtless find a need to travel with a similar level of formality to the one described here. And the general principles apply more broadly.

I can look separately at what I pack besides clothes, in hand luggage, and more general travel points.


Denim shirt by Luca Avitabile; Linen blouson by Hermes



The list below is what I might pack for a trip of five days – so five full days on location, with travel either side.

For that travel, I would generally wear something more obviously comfortable than the tailored pieces I will be wearing every day.

However, I wouldn’t resort to jeans and a T-shirt; and I always want something where I can keep passport, boarding pass etc – without resorting to my back pocket.

So a summer example would be:

For an Autumn/Winter equivalent, you could swap in Incotex chinos for the shorts, and my navy-suede jacket from Stoffa for the linen blouson.

In my hand luggage I will often have a mid-weight piece of knitwear, in case the plane is chilly. I wouldn’t wear the jacket on the plane.


Musella-Dembech cotton suit (review coming soon), with brown silk tie from Paul Stuart and indigo pocket square


One suit

I rarely travel on a trip of this length without a suit. It’s always good to know I can turn to something more formal if the need arises – for a particular dinner, or an event.

That suit will usually be navy or grey, and I will aim to have something where the jacket or trousers can also be worn with other items.

A ‘three-way suit’ like my Pirozzi corduroy would be perfect in one way, as the trousers and jacket can be worn on their own with the right partners, and can be worn together as a suit.

However, such three-way suits tend to be in more casual materials like cotton, and therefore don’t cover my need for formality. An exception would be a navy cotton suit, or a heavy hopsack.

Suits I more usually turn to, therefore, are my brown Crispaire from Dalcuore (whose trousers are quite versatile) or my Anderson & Sheppard grey-flannel suit.

More detail on all these pieces can be found at those links.


Vintage-linen jacket by Elia Caliendo, Friday Polo by Permanent Style, green cotton trousers by Reillo


Two jacket/trouser combinations

For a five-day trip like this, I would also pack two jacket/trouser combinations. So two jackets, each with a pair of trousers to be worn with them.

If the two can be swapped over, or work with part of the suit, all the better.

As with all pieces taken on a trip, there is an urge to take the most versatile, functional pieces. Examples would be:

The advantage to these four pieces is that each can be worn with the other trouser. However, if this is overkill in terms of versatility, one of the jackets could be more unusual – such as the Liverano purple flannel.

Note also that cream is probably the most versatile trouser there is, in terms of what it can go with.

The only problem is that cream trousers are not suited to every destination and season. If they are in a particular case, bring them.

With these tailored pieces, I would have three outfits for the first three days.

On the last two days, I could then wear other combinations of these, or two of the outfits again (perhaps with different shirts or accessories).


Linen/cotton shirt by Simone Abbarchi; Linen trousers by Edward Sexton (review coming soon)


Shirts, ties and hanks

Shirts are usually most versatile in a plain blue, then white – or with subtle patterns that make them no different in effect from plains.

In order to avoid this being boring, I would tend to mix up materials (eg cotton/linen) or design (a long-sleeved polo shirt for a tieless day, instead of a button-down shirt).

Ideally the shirt collars are such that they can be worn effectively both with and without a tie – as most of mine now are, whether spread or button-down.

My favourite travel ties are a navy and black large-knot grenadine. But to avoid this being too boring, I would chuck in one or two more interesting options – perhaps my dusty-orange Mattabisch.

And I always have two handkerchiefs with me: a white linen and a dark silk or wool/silk, eg the navy Drake’s I wore on Monday.

Plus one brighter selection- eg yellow and cream from Rubinacci.


Baudoin & Lange Sagans, in my colour – bark grey


Shoes and everything else

I usually take three pairs of shoes, all brown.

One pair must be such a dark brown that it can be worn with a smart, dark suit – such as my Edward Green Oundles.

The others can be mid- or light browns, but as with everything else it’s helpful if they can go with multiple pairs of trousers.

In the summer, one pair at least is Sagans from Baudoin & Lange. And even in the winter, I try to fit in a pair, as a fourth shoe.

There’s nothing worse that finding one pair of shoes – for whatever mysterious reason – becomes uncomfortable when you’re travelling, and leaving you with just one other pair, to wear every day.

Having had that experience, on any trip of more than a couple of days I take three pairs of shoes.

Socks are pretty much all my favourite dark green. They go with everything, and they have a little personality. The perfect combination.

There will be one piece of knitwear in there, that goes with almost everything – usually a navy crewneck.

Plus (if I have room) one cardigan or similar that can add interest to an otherwise versatile (read: dull) outfit. Such as a cream or burnt-orange colour.

And last of all: a lightweight scarf. It takes up hardly any room but makes a big difference on a cold evening.

Any questions, problems, or votes on future travel pieces, please let me know.

Photography: Jamie Ferguson @jkf_man


Orange/brown reversible tote by Hermes; Suitcase by Rimowa
Notify of

Inline Feedbacks
View all comments

Great Pice! Would appreciate one article on how you pack it all in your Rimowa Suitcase. Is it big enough for all this clothes?
What size is it by the way, as I’m looking to buy one in the near future



Is the Rimowa a carry on?

Also, do you bring shoe trees for all thre pairs of shoes you bring?



Simon, could you do a post on more casual summer outfits like the one in the top picture? It’s a fantastic look


Seconded. I’m based in Miami so posts geared towards warmer weather are greatly appreciated. Thanks!

Human or dancer

Please say the weight of that M.-D. cotton suit jacket cloth you intend to review and presumably wearin hot weather so I can compare with the 10 ounce weight of a RTW cotton jacket (with viscose lining) I have an eye on to wear dancing for hours.


As previously discussed, when you tend to wear parts of an ensemble separately they might show different stages of wear. So am I right to assume that you only do the aforementioned when travelling but otherwise don’t to preserve the ensemble’s integrity?




I like your blog. Thank you. You should consider writing article about ski trip outfits. That would be great.


Just to clarify is it the Duke loafers you would be wearing with the Bardelli shorts for the summer travel outfit?

Lawrence Sanbourne

Great article! I know the typical half-inside-out folding method for suits but am considering the LAT_56 Road Warrior carry-on that uses a foam folding board. Do you know if this would be appropriate for bespoke garmentry?


Out of interest – I bought and use the SPS by LAT56. It has the advantage that it can be used inside a “normal” suitcase. I’ve had a suit rolled up in it for a week with little ill-effects.


whats the watch in the 4th picture down Simon?


Very interesting Simon. How do you stop all that getting creased in you suitcase?


How do you manage to pack all this in that small suitcase, without mentioning underwear, a dopp kit etc. (would be interested to see what you use by way if the latter)?

By the way the link to your navy handkerchief is wrong. This is 2017, not 2016!


I would argue, since you were visiting two cities, Florence and Naples, that shorts were not needed. Yes, it is hot in the summer and has always been, but the ubiquity of men in nothing but shorts for all occasions is simply depressing. I was just in Rome and Naples and in Rome especially everyone was in beach wear. Nothing destroys the elegance of a town more. When I was young, not too long ago, people wore pants and generally dressed up in cities, especially Rome, even in the heat of summer. Now its shorts, flip flops (or worse, velcro trekking sandals) and sports tops and of course lots a selfies to capture the beauty of it all.


I strongly dispute this verdict. Modern cities now have bike rental programmes that provide a fun way to see the city. On very hot days riding in shorts is much more enjoyable. I was in Paris in April, temperatures were 85F(29C).

Peter K

I picked up a trick for packing shirts I have found quite useful.

After folding, place the shirt in resealable bag (e.g. large ziploc). Close the bag most of the way and then puff a little air into it before sealing it completely.

This prevents other items in the suitcase form pressing against the shirt and causing wrinkles.

I’ve used it a lot when packing shirts in my cycling pannier in summer commuting. Even linen shirts come out remarkably free of wrinkles. The only trick is to make sure you don’t put to much air in the bag so it doesn’t take up too much space.


The shirt from Simone Abbarchi looks very good. I would be grateful for the exact coth information.


Simon, may I remind you? Thank you


Hi Simon. I’ve contacted Simone to commission a shirt in the same fabric as the one you presented in this article. You describe it as cotton/linen but it really looks like a chambray or denim shirt. Is it breathable enough for summer? Also, can you give any details about your upcoming PS chambray in terms of weight and for what seasons is intended? If they are similar I will wait for your PS version.


Great. I’ll be waiting for it. When do you think it will be available? I’ve purchased all the PS oxfords by the way (including pink recently) and could not be happier.

Ian F

Very interesting. What sort of baggage weight allowance does that all fit in?

Dave Carter

Whenever I wear my black grenadine here in the UK people make silly comments about funerals. Do you get this?

Get serious

Why don’t you reply to their silliness by asking if they would please tell you if they know a more serious colour than black and see what replies you get?

Terry C.


What happened to your beloved Globe Trotter case?


Very interesting article! I salute your commitment to so much tailoring for a 5 day trip, but I travel way too frequently to deal with hold baggage. As a result, I usually make do with two jackets (one worn for the flight and one in my carry-on Rimowa) which I mix up with different trouser and shirt combos, two pairs of shoes, and my PS crew neck for the flight. It means each item gets worn at least twice, but I don’t think most people notice, and I don’t have to waste time at the check in deck / baggage carousel.


Agree with the other commenters that the outfit pictured at the top is really great. I’ve had very little success whenever I’d tried to smarten up shorts with a tucked in shirt and loafers. At best it looks rather twee, and at worst, is a bit of a “newsreader” look, but your outfit doesn’t seem to have either of those problems. I’m assuming my issue is with the cut of the shorts (I have pretty basic J Crew ones, having never really considered the idea of tailored shorts.). Any advice?


For me, the shorts and the blouson’s tonal-warmth plus texture are what make them so attractive. The desaturated yet colorful linen is in the sunlight.

Simon, A&S haberdashery makes linen shorts, do you have other recommendations for linen shorts which are not skinny and can be purchased on-line?

Many thanks,
Chicago, USA


Very interested to hear more about the PS version! Have you had any experience with the ones from PWVC? I notice they weren’t featured in your top picks for summer article…


Are there any online retailers for Bardelli? Even better if they are UK based for speed of delivery


Which brands of tailored shorts would you recommend then? Struggling to find anything online that arent overly casual


Personally, I find it preferable to have my butler travel ahead with all of this stuff.
That way she can have everything pressed and organised for my arrival.
For the price of an economy ticket and a cheap hotel nearby – it has to be worth it.
The other advantage is, if she forgets anything , I can always bring it with me.
That said, she knows that forgetting is a disciplinary offence!
As for packing – thankfully I can’t remember the last time I had to do that.
Nice case though – I’ll have her order a couple.


Wow ! Can you also get your butler to comment on your behalf ? She might add add more useful comments as she is one doing all the packing.


The main thing is colour co-ordination.
With the exception of leather jackets – most of Mr David’s attire consists of different shades of blue and grey and by looking at his schedule and events I find it easy to pick what he needs. Simon gives great advice on how to pack and I certainly try to avoid creasing but I can always take care of that on arrival. One important point is I always have A&S sponge his suits before I go. Mister David hates dry cleaning.
Another important point is luggage. Frankly I’ve looked at these Rimowa cases and they aren’t a patch on Tumi.
Tumi are the best when it comes to serious luggage because they are so tough. I don’t have to do a lot of wheeling because we use porters and drivers but when I have had to move a case, Tumi’s wheels are great. Hope these tips help.


Dear Simon

What are the dimensions of your RIMOWA suitcase (But, alas, you do not have the Junkers plane to go with it) for a five-day trip?


JP (Paris)


Hi Simon,

When you pack shoes do you include trees? I ask as I am currently sitting in a departure lounge and moments ago had to pull out my shoes at security (the springs inside the trees were the reason).

Just wondering if there is an ideal alternative for next time when not checking in my bag (as I’d hate to stuff my Edward Green’s with socks as a DIY tree for holidays)


Hi Simon – love this article. I was also interested in your choice of luggage so I’m glad it came up in reader’s questions. It’s something I struggle with – either lugging round a huge family suitcase half empty, or even worse, taking too small a bag and being faced with having to re-wear socks and pants more times than I’d ever admit to on this blog


Hi Simon,
What are your thoughts on recent news regading workplace dress codes? I refer to MPs no longer being required to wear ties in the Commons. I also recently read an article (in the FT, I think) about JPMorgan extending their dress down fridays to cover the other 4 days of the week…

Nick Inkster

Agreed Simon, but what is worse is the shocking lack of style amongst MPs tie or not. Suits that don’t fit, shirts collars too tight or too loose, sleeves miles too long, shirt/ tie clash. And it seems that the “stylists” have persuaded them all to go dark suit/white shirt/satin shiny tie.

I recently found myself standing next to the leader of Her Majesty’s Official Opposition on a railway station concourse. Good grief.

Maybe the idea is that you are so shocked by their appearance that you don’t pay any attention to the drivel they mainly speak.


^^ I completely agree. You wrote a line several years ago that I am still struck by; that you aim to “dress simply but well”. Simply doesn’t mean lazily.

Thank you for all the work you’ve put into this over the years


It’s the thin end of the wedge. Some of us live at the thick end, and it’s ugly as sin.


Great post, thanks, I’m thinking of buying the cleverley reindeer washbag, aside from cost, which is high, does the leather wear well and any other suggestions for high end leather wash bags? Thanks


Firstly thanks for taking the time to put this article together – I love articles such as these. To round off; 1 travelling outfit, 1 suit, 2 sports jackets, 2 dress trousers, 3 shoes, 3 ties, 3 hanks, 2 pieces of knitweat, a scarf. I particularly like the thinking around green socks. I would add the copper Shibumi tie, it just looks so great and the texture would work with the blue cotton suit. I’d also swap out the Solito (never really liked it) for the Caliendo tan linen/wool jacket, match it with the Paul Stuart green linen trousers and replace the cavalry twill (not really understood outside of the UK) with the grey Crispaire trou from the Disguisery to match the blue hopsack – plus I think the silhouettes would marry better. My only other comment is that travel practicalities are not covered; the need for rainwear, exercise wear, sleepwear, eyewear, umbrella etc. Perhaps this could be covered by an accompanying article on travel accessories? Pierre Cardin once said that after many years of travel he distilled his wardrobe to 3 necessary outfits; 1. blue suit, 2. sports jacket and grey flannel trousers, 3. dinner jacket. However I think this a little limited, especially across 5 days or so. By the way the Abarcchi/Sexton combo looks great – looking forward to the review.


I’m curious on your thoughts on “comfort” shoes. If you are on a trip where you expect to spend 8+ hours on your feet sight-seeing, which shoes would you pack? Presumably you won’t be wearing your Sagans for that, and I assume the Oundles are not the most comfortable for that amount of walking (and you probably don’t want to risk their getting damaged).

Thank you in advance for your thoughts.


Simon, can I buy the Bardelli shorts anywhere online? Thanks!


Hello SImon,

What will you recommend for a 15 days European trip in Autumn/ Winter?
Also, will you bring 15 different shirts for the trip?



Hi Simon,

Nice bomber jacket! What is the weight of the fabric, and is it lined? Would it be better with a thin fabric and lining, or a thicker fabric? Thinking about pockets and similar..


Hi Simon

What’s your solution for bulging pockets when travelling? When I take city breaks (as opposed to more rough and ready holidays) I’m usually at a loss as to how to carry the various items I need with me when sightseeing or wandering around a city – especially in warmer climates where I may be wearing some light trousers or shorts and a shirt or polo. I usually have my phone, a small camera, wallet, sometimes a travel humidor for cigars, and I ways end up juggling everything in my hands. Even if I’m wearing a light jacket the items cause unsightly bulging if I stuff them in my pockets. I was considering some sort of small ‘day bag’ but everything I’ve found seems to lean towards the messenger bag style which seems a bit ‘young’ and lacking a bit of sophistication.

Many thanks


Christopher Vinson

What about a nice dopp kit? I’ve also had trouble finding stylish, yet functional toiletry containers that don’t leak from airplane pressure.


Hi Simon, very interesting post. You have mentioned the three-way suit here and elsewhere on the blog a few times. I know it is not the ideal thing, but I travel frequently for work, often with limited luggage (not so much because of airlines but because of needing to share cars at the destination with colleagues) so it is to have a suit can be worn both formally and casually. Any chance you might do a post on the three way suit? I suspect it would also appeal to those of us on more of a budget and starting out on the bespoke journey. Thanks.


lovely atricle


How many suits would you pack for a three day trip wearing a suit every day?
Would you pack three suits? Or two suits with one additional trouser so that you can wear every day a new trouser and one suit jacket two times?

Generally speaking, is it ok to wear a suit two times on a business trip because ideally a suit should only be worn once a week?


IMHO, an update to this topic would be great for the upcoming summer (What you pack when travel). As readers might have noticed some aspects of your style has changed, for example, I can see you have incorporated more and more high-quality casual items in your wardrobe. It would be interesting to see.


Hi Simon. I can’t seem to find the link to the Edward Green Tan Suede Loafers. I’m looking to get a pair of suede loafers for the summer and am comparing the EG Polperro versus the Baudoin & Lange Sagan (preferably Ginko). Any thoughts on the 2?


I highly recommend the unlined Duke from EG. Supremely comfortable and stylish, if you like a more classic / robust shape than B&L and something more substantial than the Polperro. I have a lovely biscuit coloured pair that gets ten times as much wear as the Polperro loafers which are just to flimsy and loose for my liking