Tailoring for travelling: tough, comfortable, plain

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In our recent articles on menswear destinations in Rome, a couple of readers asked about the outfit I was wearing for beating around the hot city. 

The individual pieces should be pretty familiar: 

The reason they were chosen, however, is to do with travel and work - working travel. 

All of the clothes had to be able to put up with a good amount of abuse. They were sat in while flying, they were worn two days out of four, and they received neither a press, a steam or even a brush along the way. 

The cotton jacket is particularly good in this regard. A vintage cloth that Nicoletta at Ferdinando Caraceni picked out from their archive, it is a little coarse, densely woven and tough. 

It doesn’t rumple in the way a lighter weight cotton would do, nor wrinkle like linen. It’s strong enough that you can wear it every day, and use the pockets perhaps a hundred times a day, to retrieve pen, wallet, phone, again and again. 

Dense cotton is not as cool as lightweight linen or wool/silk/linen, but neither would be this tough. I choose it for a working trip like this because it’s reliable, and I never have to think about it. 

The jacket’s other advantage is that it’s clearly smart, but not business-y. And while it clearly has some style, it’s fairly plain - the kind of thing people are unlikely to notice at the expense of you or your questions. 

Plain clothes are also easier to add items to - a tie, a handkerchief, a knit - when circumstances dictate.

High-twist trousers are a bit of a no-brainer. They’re the best material for retaining shape, and for dealing with a similar kind of abuse to the jacket. 

Ideally though, these would be the Drapers four-ply rather than two. The slightly heavier weight wouldn’t matter in terms of coolness, and I’m a little scared of wearing this pair through eventually, even though they’re hard-wearing. I just wear them that much. 

Perhaps I should have a pair made in the four ply. These ones were made the lovely Nicola Cornacchia and family, and they are nicely fitted. But the make could be a bit better and I’d prefer a slightly higher rise too. 

One to think about in February or March next year perhaps, for spring and summer. 

The shoes aren’t especially tough, really. Suede is a little delicate (except when it comes to rain) and these don’t have rubber soles or even a double leather sole. 

But the most important thing in a travel shoe is probably comfort. There’s nothing worse than being in pain when you’re trying to walk around city, inevitably a little late for the appointment, inevitably a little lost. 

And unless trainers are an option, your feet are always going to get tired. It’s pain, blisters and so on, that are the killer - especially when it’s hot and your feet swell.

It’s actually surprising these Belgravias are so much more comfortable than the lined version. 

After all, there’s still a lining around the heel, under the toe, and around the topline. The latter is required on the Belgravia (unlike, for example, the Piccadilly) because of its braided leather looping in and out of the shoe. This needs to be covered up. 

So the only part of the shoe that’s actually unlined is the lower half of the two sides, from the arch to the joints. This clearly makes a difference, but there are other little differences, such as a lighter sole, which perhaps make as much difference as the fact they’re ‘unlined’.

I should also say a quick word about the socks, as I seem to wear only two colours of long sock these days, ever. 

They are the dark-taupe cotton model from Anderson & Sheppard (pictured) and the normal taupe.

They’re very well-made socks of course. Fine mercerised cotton, hand linked, stay up well: luxury pieces suited to bespoke tailoring. You can get the same from Bresciani, Mazarin or Pantherella. 

The thing that separates these is the colours. The fact they’re both described as taupe could seem limiting, but actually the dark taupe goes well with pretty much every dark trouser: charcoal, grey, navy, dark brown. And the taupe goes with almost every light one: beige, khaki, olive, white, cream. 

They’re harmonious, but they also don’t match, so they also provide some (subtle) interest. 

On the subject of white or cream trousers, I used to wear them with a very similar sock, but in retrospect that was too stark. Something like taupe or beige is better, even if it theoretically lengthens the leg less.

So, versatility of taupe socks. A small thing, but I guess worth highlighting if you’re the kind of person that doesn’t need more than a couple of pairs of really fine socks. 

I feel like there must be more of those today. People that still love tailoring, but realistically only wear it a couple of days a week. 

In terms of travel, the advantage of those versatile taupes is that they can easily cover more than one pair of trousers. Just in case you change what you’re going to wear one day, or get a hole in one (in a bad way).

Photography: Milad Abedi

P.S. Yes, all but one of the cuff buttons are undone in the third image. But no, I still don't generally advocate wearing jackets like this. I had merely undone them to show someone the work on the inside of the (unlined) sleeves

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Nice article with beautiful photos, Simon and team. When comfort is a priority in shoes, shouldn’t B&L Sagan work well in this situation? Or is it because you also had to walk a lot and the Sagan would be not supportive enough?

peter hall

I’ve discovered that a good sorbothane insole removes much of the foot ache when wearing loafers or lighter boots for extended walking .


Thank you – all very persuasive; but why a DB-jacket given the heat?


Thank you. If I may: Is that more a recent development? I do have your post on un-done-DB in mind – but also remember an older one, where you emphasized the beautiful blue-DB-caliendo jacket as a perfect travel-jacket if it were not DB…


Hi Simon,
Great article on clothing for traveling and wonderful photos of Rome.
However I do have a question on socks. I often struggle with wearing casual socks with trainers at the weekend. I find that most mid calf socks don’t stay up as well as over the calf ones do. And I would rather wear a somewhat more simple athletic one with good quality.
Do you have any suggestions that work with trainers and denim or casual chinos?
Kind regards,


I like H&M in a set of seven short socks.


Taupe is such a great color for menwear, but somehow I never thought to try taupe socks. Maybe because it’s not such an easy color to find RTW. As you say, as an accessory, it compliments most other colors without trying to match them or compete with them. But it can also be the dominant color in an outfit.


Hi Simon, as you know I am biased but I find this one of the most flattering jackets you have. The long curved lapels and strong shoulder create a more masculine look than less structured jackets, that I think suits you really well. Great photography as well by the way.


Completely agree Andrew,
might as well go for something proper if you’re wearing something that is considered ‘formal’ by most nowadays.
I think people make the mistake of always trying to dress down(and thereby move remove the purpose of) something more elegant/flattering in order to turn it into something that attempts to play chameleon in a dressed down world.
When really, it never does.


I’m talking more so about the cut & style of specific items,
the worst offender of my previous complaint being these Italian knit ‘jackets’ with no canvas, barely there lapels and 10 inches too short. Basically trying to turn the silhouette of a jacket into a casual jumper, this is something I don’t like.
I love certain forms of high/low (with restraint), I frequently wear an old 4×2 Gold buttoned blazer from Brioni featuring strong roman shoulders with a well worn and faded (no tears) pair of Levi’s 501 and black loafers.
Although, I know this combination may only work because I’m still in my twenties.
I think a tailored jacket simply looks its best when it has shoulders, length and presence. No matter which context it is placed in.
(This may vary according to body type)
I think the examples you gave are great looks, but each element has to be the ‘thing’.
By this I mean the jeans in your suggestion should not be one of these pseudo formal jeans from many Italian makers. They need to be proper jeans, preferably in a mid wash.
PS: I recently inherited an old thornproof tweed jacket from my Grandfather made by Chester Barrie, must be at least 30 years old.
Although it has very traditional features like a long skirt, hacking pockets and a bellied lapel, it has no structure whatsoever in the shoulders. It can be collapsed, almost like these modern coats.
Was this a common way of making tweed coats at the time?
I think it’s an extraordinary piece because it has no internal structure yet drapes and looks very structured due to the heavy tweed.
Would love to know if you have more info on that.


Choosing the right clothing and shoes for a short business trip is very difficult particularly if “only hand luggage” is the top priority. In your specific case (August in Rome) you had the advantage of being able to disregard the rain factor. For a 2/3 day trip would you wear the same shoes for two days in a row ? If not, do you take shoe trees with you ?

Joe P

Hi Simon,
Are the socks plain rather than ribbed, and is that generally your preferred style now? How casual would you go with those particular ones: white denim and workwear chinos for instance, or are they too dressy for that? I often tend to go dark green as a catch-all, as it’s strangely hard to find neutrals that work across the board as these ones seem to. Thanks.

Joe P

Thanks, Simon. Could I ask what mid-calf taupe socks you’ve found that you wear with ecru denim? These A&S ones don’t seem to come in shorter lengths.


Tabio has quite a few taupe pairs in ribbed and non-ribbed at a mid-calf length. Unfortunately, I cannot attest to them as I tend to stick to knee-length.


Thank you for your interesting and informative article.
I have a more general question about dress socks, since I have started wearing (and buying) them more regularly.
A pair of good dress socks cost something between 25-35 pounds, at least. I’ve found that I can wear a pair about 20-30 times before it starts having holes. I can extend their lifetime a bit with mending them but not that much.
Has that been your experience with such socks? I love wearing them, but it feels a bit frustrating to invest that money in a nice pair of well-made socks, only to have to dispose of them relatively quickly (at least compared to other clothing items such as sweaters or trousers).


Thank you, that’s interesting.
I am washing them cold, so I think that’s not the culprit. I am wondering whether it has something to do with my shoes, since the holes appear in the same spots (at the beginning of the toe box). I wear dress shoes, but not yet bespoke ones; I will commission my first one this fall, perhaps I see a difference.
Budget-wise, I’m fine to paying for nice dress socks; they are absolutely wonderful to wear, and I can afford them.


I remember you saying this is not a very versatile jacket because it’s only good with grey trousers… does this still hold?

Guy W

Really like the practicality of this article, thanks Simon. I’ve also recently discovered how versatile and subtly different taupe socks are. I bought some for more casual trousers and found they worked equally well in more formal (ie work) settings. A question on socks, do you prefer cotton over linen in summer? I bought a few linen pairs thinking they’d be drier and cooler than cotton and equally hard wearing (if not more so). I haven’t found them to be very hard wearing, maybe mine were a looser weave but they developed some holes rather quickly at the tops of the toes. As a result, maybe mercerised cotton is the way to go but I thought linen would be better in the heat.

Also, what’s the point in crew length socks with casual clothing, like chinos and jeans, if they don’t stay up?

Guy W

Thanks Simon, I hadn’t really thought about the formality of the sock height, but it definitely makes sense. I guess I just haven’t found the right crew sock that doesn’t completely collapse. Any recommendations?


I haven’t had a good experience with Uniqlo crew socks, in regards to them staying up (their no show socks are fantastic though). So far the best I’ve found in the price range I’m willing to pay is Falke.


Great article. I have been wearing unlined EG (Padstow or Portland in Suede) a lot this summer, and they are indeed very comfortable especially in hot Med weather when the feet easily swell. But I would go further and usually wear hidden socks. Very breathy. So when do you decide to ditch your socks (even when in a cotton suit) and go sockless?


Very interesting. How did you find the dense cotton jacket to travel with? I would have thought that the lack of stretch would make it feel like a coat of armour whilst a plane or train. But the again we are all accustomed to wearing denim when travelling which is just as rigid.


Hi Simon,
For summer travel, I find wool/linen blends in an open weave, drape better, wrinkle less, and keep cooler than cotton and so are better suited for a jacket in warm weather. A jacket in this fabric without canvas (some structure at lapels) has served me well during travels in the summer months. An unlined full canvas jacket in hopsack weave also works for me, and I take a second navy jacket for evenings or more formal events. For trousers, I also prefer high-twist/fresco wool, over linen, as even the heaviest linen loses shape by evening.
I don’t wear loafers generally (when traveling for work) but lighter shoes with single leather soles and linen socks work well for me. I also always take a second pair of shoes with me unless returning the same day, and often a very light trainer to go to the gym or walk around parks/hills after work. All these and 5 shirts and three to four pairs of trousers easily fit in carry-on luggage.


Hi Simon,
very helpful article.
One question related with this article, I think it addresses an issue many might find troubling.
The biggest issue in my wardrobe are socks, more specifically whether to wear over-the-calf socks or “normal” (mid calf) socks. With tailored trousers, I always prefer over-the-calf socks but nearly always have to pull my trousers down. I wear trousers with a quite slim hems – 17-20cm, as many of us do on the continent…. and I do no like the look of wider hems.
I have tried various sock-materials, with very thin Fil d’Écosse cotton being the best to counter this problem, but still far from perfect. Do you use a smoother/more slippery sock material, maybe silk or even synthetic to counter this problem.
Kr Markus


Thank you Simon. In fact it seems to be a 17,8 or a 18,5 hem with tailored trousers from the brands I mainly use (Cavour an Pini Parma). I am rather short (175cm) and only weigh 65kg from tons of cycling and running. So my jackets are also quite slim and the whole fits together (makes me appear rather taller), I believe. On part of tailored trousers, slim fits me best, however with a light taper or pleats because me upper legs are rather strong from the sports I do. If you have another brand suggestion for trousers, this would of course be highly appreciated.


Thank you again. Great help, as always.

Dan James

This article couldn’t have come at a better time.
First, as it allows us all another look at one of your finest jackets. It really is beautiful and never fails to impress.
Second, I have 2 week trip to the UK, France and Spain coming up at the end of September and beginning of October and this has given me a lot of food for thought. I don’t have a durable cotton jacket that will survive that length of time so two jackets (1 wool-linen and 1 pure linen) to swap between formal and informal. I run hot so you’ll have to forgive me for the linen. 2~3 pairs of trousers to match both jackets and enough shirts to last the first week and make use of a laundry service in the middle weekend. All of the items will be plain to be un-noticeable but still smart.
I can only hope that the warm weather persists but a raincoat might still find its way in my suitcase. Do you know of a ‘good/reliable’ packable raincoat?


Suggestion on socks seems quite popular and useful, I think I’ll also take advantage of that, shade of colour seems key here.

Regarding soles on the EG loafers, you would prefer rubber, like some kind of “city sole”, for traveling? I think for comfort you would even want Blake construction but that coupled with unlined make wouldn’t be something I call durable. I once had unlined suede loafer with classic Dainite sole, what a mistake that was- neither elegant nor comfortable.


Hi Simon,
Actually, the title of this post could have been: “Tailoring For Travelling: Tough, Comfortable, Plain and … chic”!
The whole post is so instructive that I’ve already read it twice! Any item you mentionned is really worth pondering: the jacket, the trousers,the loafers and last but not least the socks! What you said about the latter is absolutely compelling! I don’t know if all long-time PS readers would agree with me on this, but I really think that your suggestion on this specific topic is the best compared to the ones we usually consider when having to wear a similar outfit.
Personally, my usual choice in such a case has been inspired by Ethan Newton at Bryceland & Co, That is, a pair that matches the color of the loafers, and thus expectedly dark brown! Mind you, it was a sounder alternative to the navy usually favored by Italians!
As to these loafers made by EG, I couldn’t help but muse over how great tradition and skills are reflected in their construction. They are truly amazing!
By the way, a word could have been added with respect to the link between outfit and environment…
Thank you for this very interesting post, Simon!


Great article, Thanks Simon. I have been considering to make a summer travel navy jacket (probably with MTM). Against wrinkle and damage with a good breath, I heard high twist is the best option. But whilst many wears tropical wool trouser, not much on sepearted jacket. I find Hopsack is kinda risky with travel. How´s tropical wool jacket for traveller compare with Cotton? Lite Fresco HM, Springram 2ply, Eco Traveller HM I consider in British ragne.


Thank you for your answer, Simon. I have a one kinda worsted Hopsack off the rack jacket, but it makes long lasting wrinkle so easily after a trip, so I was afraid of that Hopsack is not appropirate for the travel. I gonna look up HM Mock Leno, looks super.


Hello Mr Crompton,

Firstly, I would like to say ‘thank you’ for your continuous endeavours and ever-lasting enthusiasm for the elegance and beauty of menswear that we all appreciate and love. I am a newcomer to London as an international student. Before moving to the UK, I have already gained a little experience in customising my own clothing in Japan and China to have some essential elements ready in my wardrobe (during which what you shared with us provided an important source of inspiration). Yet still, I know a little about things around here other than what I have read from your writings – which I enjoyed pretty much, and a few other correspondents I have followed for a while.

Now I am planning to visit a Savile Row tailor for the first time, with a budget of 6000 pounds (this is not a fixed number, but hopefully not to spend too much on one single piece of clothing to realise more considerations simultaneously). Therefore, if that were at your convenience, I would like to seek advice from you on where to go and how I should spend that budget. Considering my limited budget, I welcome those shops with innovative offshore manufacturing options, such as Cad and The Dandy, Steed on Savile Row, and Edward Saxton as well.

Again, thank you very much for your time on my question (also my gratitude to those gentlemen who would like to share their wisdom about my question).

Yours sincerely,


Dear Humphrey,

Thanks for relevant question. I am not an expert in any shape or form – however, from my read – it seems you can have a good (and within budget) experience with Whitcomb and Shaftesbury. Give it a try and share your experience either ways. Good luck.



Hi Simon, when you caught up with Anthology did you see their fawn cotton DB jacket? It was relatively solid fabric (almost sueded), but the colour and texture was amazing. Curious to know how you casual you think that type of jacket could go.


Hi Simon. Thanks for the article.

How do you care for your clothes when you get back home? By which I mean, if you’ve really beaten them up whilst away in a hot city, what do you do to return them to their previous state? Would you just arrange a sponge and press or are there other things one should do for fine clothing?


Hi Simon,
I did a little search and could find some articles on people doing professional sponge, but not living in London and not having bespoke suits I would be very interested on learning to do it myself. May I suggest an article like the one on how to deal with certain types of stains, but showing how the sponging is done?
I also found an article or two outside of this site, but I would trust an article here more 🙂


Yes, that one has saved me more than once already 🙂
I was wondering if there is more to the sponge process than the spot cleaning shown there.


I see you have come around on unbuttoned jackets. I like the relaxed look.


The sport coat looks amazing and I could see it travel well. What is the easiest way to get one?


Hi Simon, very interesting article. Our styles are definitely different. I’m a more middle of the road, definitely less elegant sort. But I think I have found my all purpose shoe. These are a moderately slim split toe penny loafer in a dark brown but with a lightweight commando sole. Sounds horrible but the sole is on the conservative side and the toe shape is round/almond but not bulbous. Works with jeans, wool trousers, chinos and in an extreme emergency walking shorts.


Very interesting comment about the heavy cotton. I have a suit from Drake’s and was surprised how well it functioned in the heat. The stiffness of the trousers with the fairly relaxed fit, did allow air circulation. Generally I’d go for high twist, but as you observed, something more informal was needed, and cotton was the perfect compromise, in a way that even linen would have appeared too formal.


Are the pants flat or pleated? You seem to be wearing more pleated pants these days.


Hi Simon,
Would you consider a jacket in the Ascot 4-ply for this weather or just trousers? It’s a great fabric, being both high twist and tough as nails, just curious what it’s limitations are in your mind.


Love the outfit Simon. Do you take a translator on trips like this?



Do you mind providing a fabric code for the trousers? These look great here, just a touch lighter colored than the grey odd trousers I wear from this bunch. In the past I’ve went a bit too light grey and they were less versatile. Curious as to this shade. Thanks.


Sagar G

Hi Simon, I’m Sagar from Chicago. I have been following your blogs for quite some time now and I must say, your content made me change my view towards the wardrobe. https://s.w.org/images/core/emoji/14.0.0/svg/1f60a.svg Your blogs and videos are very informational and contemporary. Thank you for that. So, now I’m slowly building my wardrobe but having an issue with access to good tailors. I’m seeing that every custom clothiers offer access to European fabrics but the fit and style are always questionable. And using European tailors with trunk shows or visiting in-person adds up overhead costs. Can you please share/create a blog on affordable quality tailors in USA? Or if you do have one then I’d love to know.
I think you can agree that not everyone can carry a huge budget for the wardrobe. So, I’ll appreciate your help on this.

Sagar G

Hi Simon, thanks for your response. I am requesting references for good bespoke tailors from USA (Chicago preferably) irrespective of whether they offer MTM or not. I like your content about the capsule wardrobe where you mentioned the tiered structure and later on shared the potential tailors. Most of them are from Europe. So, if possible will you be able to share a similar list of bespoke tailors from the USA? Thanks.

Sagar G

Thanks for the clarification. This is my experience too with a US-based tailor. But thanks for sharing the article. I will review it.


This tailoring for traveling article was a pleasant read. I know these three are different style-wise, but I was wondering how did you like these Belgravia loafers as compared to the Capri from G&G and the Sagans from Baudoin & Lange in terms of comfort and durability. Thank you in advance!


Gotcha. This will be my first pair of high quality shoes I’ll be acquiring. I am definitely more in the casual chic camp with semi-smart trousers, oxfords shirts, and jacketing. I have been pairing them with my white sneakers, dark brown suede desert boots, and medium brown adelaides. Would the unlined Belgravia be a good option to be add to the rotation or should I go with the fully lined version of the loafers? I do walk a decent amount since I live in Boston.


Hi Simon – are your trousers grey or taupe like your socks? They seem to have some brown in them.


Hey Simon, great blog!
Two quick questions:
1) Reading your post – fair to say then that cotton (c.13oz) will be more durable than heavy linen? (I’m thinking about damage-control at drunk weddings ha)
2) I’m looking to get a dark olive 13oz cotton suit made (MTM: Amel, Anglo-Italian, Moreau). This would be my only cotton suit (I have a navy high-twist wool S.Amel suit for summer. For winter I have grey flannel), and I’d like this to be for weddings/slightly more casual affairs.
Question: Which 13oz cotton would you recommend for versatile dark olive?
(you said in the comment section that your Ciardi cotton choice could have been a bit darker: Drapers, Cotton & Cotton 4844, 13oz)


Thanks for getting back to me on this – really appreciate it! All the best


Thank you Simon for the recommendation of taupe socks. I can also recommend the „vulcano“ color from Falke. I think it is quite nice with my ecru Rubato. But I agree that a light or mid grey is the logical choice if I am wearing sneakers. Speaking about Rubato: have you seen their natural color socks? The color looks useful (and quite taupe) online. But they are wool so maybe again a bit smart for denim.


Hi Simon, do you take the same size for both the lined and unlined versions of the belgravia? Thanks.


Hi Simon. I was wondering about sizing of unlined Belgravias. Did they begin a little snug in the width and loosen out ? I seem to be snug in one size and falling out of a half size above ! Length is fine in both. Would be grateful for any advice or experience you may have ? Thanks as always !


Hi Simon, wouldn’t the unlined loafers give you even less support around the arch areas? and eventually, make the feet more tiring and uncomfortable?

Many thanks,


The color of those socks really is excellent. Perfect for the kind of cold colored wardrobe you’ve talked about before. I do prefer wool though, and finding something similar has proven to be an unexpected challenge. Rubato offers wool socks in great colors, for example, but only ever in a shorter length. Plenty of brands offer long wool socks, but primarily in brighter/warmer colors.
Do you know of anyone that offers these colors, with an over-the-calf length, but in wool?


Hello, if I am in between sizes (8.5), do you suggest a size down or up with the dress socks?