how to dress for travelling

Attire for flying out to Florence this week.

Polo shirts make great travel items, particularly long-sleeved under jackets. They are comfortable, cool and versatile, and navy is the smartest option. Just make sure the collar is tall enough to not slip underneath the jacket, and tuck it into tailored trousers to retain both formality and a flattering line.

I tend to neutral colours anyway, but a navy polo is best paired with a navy jacket, in this case a cashmere version from Solito in Naples. Avoid navy shirts, however – if you want something darker or non-corporate, try shades of grey.

Fresco trousers from Gieves & Hawkes, fresco being particularly good at avoiding creases when travelling. Slip-ons in hatchgrain leather from Gaziano & Girling (on the off chance you have to remove them in the airport). Weekender from Bown, with Talarico umbrealla (the week promised thunderstorms, though none emerged) and my Sac a Depeche in the other hand. Dark hank. 

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Per Arvidsson

Very nice outfit and also nice photography, whoever is responsible should pat themself on the shoulder. I’d like to hear your opinion regarding fabric choices for long-sleeved polo shirts. All my polos are 100% cotton and I’ve not yet tried wool; how do the Smedleys wear compared to cotton ones?


Forgive my ignorance Simon but I always thought all polo shits were made with knit cotton (in order to be more breathable and durable, per Rene Lacoste’s original design.) If they are not knitted, what are they made from and where do you get them? Am assuming they have to be made bespoke…?

Great outfit by the way.

Paul Weide

Much preferable to the powder-blue velour tracksuit with a word embroidered on one’s rear end.

Michael Murray


That is truly a great outfit. Permanent Style is a constant inspiration for great outfits for all occasions. I just obtained a Zegna blazer at a deep discount and I am going to look to pattern a outfit after this picture.

All the best,



Thank you for your earlier post about long-sleeved polos. They are remarkably practical when casual-wear is acceptable, dress down or up well and breath nicely in the heat.

Interested in your preference for navy, tho’. My concern is that there is too much of a risk of a clash with the classic travel coat (a blazer). For me a heather grey long-sleeved polo is for casual shirts what the ‘pale blue shirt’ is for dress shirts. It may help that I tend to wear mid-to-dark grey trousers, so there is always sufficient contrast between the polo and the trews.

Kent Wang does very nice long-sleeved polos at very good price:quality. I particularly like the single button-cuff he offers and the slightly more structured collar.

Andy Liu

Hi Simon:
Nice pic! Are you wearing OB polo shirt in the pic?
How do they hold up the shape after a couple of wash?




Simon, your travel outfit is outstanding and your recomendation of long sleeve and the color navy for the polo is absolutely correct. I have several short sleeve Riviera model polos from Sunspel that are fantastic. The company also makes a long sleeve model as well that appears to be a true polo. Do you have any experience or knowledge of the Sunspel long sleeve polo?


Simon, I think you’re right about that. The Smedley cotton polo,Finchley I believe, may be the best choice for me for Spring/Summer wear and the Dorset wool model for Fall/Winter. Would you agree?


Talking of shirt alternatives, is there another Dartmoor production planned?

Sarah Gilfillan

Great outfit! Interested to hear why you suggest to avoid a navy shirt though? Personally I would be inclined to choose this (for my clients) over grey which I find can be a little austere. Interested to hear your thoughts.

Sarah Gilfillan

Thanks for the reply Simon. I’ll take your advice and try out some grey on future clients.


I agree with you,but appreciate Simon’s prespective.



Are you planning a post on this (new?) Solito jacket? Further, are the lead times at Solito still roughly a year?


Wow Simon, that is a very nice ensemble


May I ask why a navy shirt should be avoided?


I was wondering too.
A dark blue shirt, untucked and no jacket & a black beret is something I enjoy wearing.


I have been following your blog for the past six months or so. I love it! The only unfortunate part is visiting some of the organisations you mention (and recommend) and coming across awful customer service. TBH the traditional English brands are particularly poor: I have come across head cutters at some (highly esteemed) bespoke tailors who appear to have little time for potential customers and sales assistants who take a high-handed approach to selling. In this regard, I think the UK is well behind some of its European counterparts. Clearly the sales aspect is important and, for some, as important as the items they’re selling.


On the issue of Solito….6 months isn’t terribly long to wait. Have you moved on from Caliendo, or will you be commissioning jackets (no suits it seems?) from both?

Paul Weide

Related question, Simon. What are your thoughts on the turtleneck? Do you own one?


Dear Simon,
same question as above, why should navy shirts be avoided ?


Why not shoes or hats?
I have a lovely pair of blue suede brogues that are really rather dapper and go very well with grey trousers


Lovely jacket Simon, what mill is it?

Bertie Wooster

Simon, any other similar recommendations or alternatives like the Weekender from Bown? Thanks

Bertie Wooster

Great! Please oblige if time permits, or just drop a few names as I need one soon 🙂



Love the jacket. What jacket length do you go for on odd jackets? Should the jacket still cover the buttocks fully?



excellent response Simon! Quite frankly, I’m getting a bit annoyed with men who wear their jackets too short as is currently fashionable. The current trend makes men,in the immortal words of Tom Ford, look like flight attendants.


Simon — thinking about trying out Solito on the next London visit. How much did your jacket cost?



Really nice. Was just recommended by a friend.

My 2 questions:

– What would your attire be for traveling overland y public transport in places like Albania or Turkey (outside Istanbul)? In all seriousness; they are nice places, have been there, and people also take care of themselves, but as you can imagine, it’s not Florence. In fact, I am more interested your whole wardrobe for a week than just one outfit, including the bag you’d carry around by yourself.

– You are a well respected journalist. What would be a comprehensive book you could recommend to a beginner like, who wants more than just posts and articles, to “learn style” from level 0?

My attire is, yeah, as said previously, to travel to similar places in style w/ bag. – might be too utilitarian, but preferably style with function. I appreciate your work.


What’s the weight of the cloth used for your Solito cashmere jacket?

D. Jordan

Dear Simon,
I will be undertaking a very long flight [almost 24hrs] in the near future. I would like some advice as to the best options to consider for what to wear for such long-haul travel. I will be travelling business class, with time spent in first/business class lounges between connections, therefore it will obviously need to be smart. However standard smart-casual: jacket, chinos, loafers, long-sleeve polo etc, won’t do as there will be a decent amount of time sleeping in what is as close to a bed as an airline can provide. So what could I wear that has the comfort of “lounge-wear” but is tasteful/acceptable for such semi-public circumstances.
With thanks,


Hi Simon,

I was with Luigi Solito yesterday and was discussing getting a jacket like this made for myself. He didn’t have the same Zenga cashmere cloth you used. He recommended the Loro Piana Top-China 554017 or 554022, both of which were 10.5 oz (I think an oz heavier than yours) twills of different tightness…What are your thoughts on a twill version of this jacket (I assume yours is a plain weave)? What about midnight blue instead of navy?


Hello Simon, did you ever have Fresco made up as a suit or just trousers? I’d guess Hopsack is more of your summer uppers fabric but wanted to confirm, also on 8/9oz Fresco vs. 9/10oz for either suit or trousers. Any thoughts? Many thanks

Jackson Hart

Hi, Simon.
A few years ago I commissioned a med grey 9/10 fresco jacket. It’s very soft, so appropriate as an odd piece, so I thought. I am having trouble pairing it, however. ‘Any suggestions on what trousers to wear with a med grey jacket? Blue seems to create much more of a severe contrast than I am accustomed to wearing and most greys are obviously out of the question. How about very dark charcoal grey? Do you believe that fresco is textured enough for an odd jacket? And do you think it looks to “summery” to wear in the winter? And while I am on the topic, can hopsack be worn in the winter or is just a summer material?
Thank you, in advance, Simon.

Lindsay Mckee

Great Post. I’m a big guy, size 50″ chest, and I find that Lacoste Classic Polo’s in large 3XL in long or short sleeve are just great. Very hard to find my size in jackets and even trousers unless MTM or bespoke but as always, I’m willing to try new brands. I look for quality at all times.
Thanks for this post.


Nearly a decade after you posted this and I looked it up because I’m travelling this weekend. One thing that occurs to me (and which you’ve written about before) is how much difference the shape of your beard, the shaving of your head, and a bit of a tan makes to your appearance. Along with a little more build, you look significantly better nine years older than you do in this photo, which isn’t in itself unflattering. I think this aspect can be lost sometimes with the focus solely on the clothes. Even your posture seems better in more recent photos.

But anyway, on the off-chance you see this I had a couple of questions about this outfit. Would you still wear it, in this particular way, today? I think the navy polo with the navy jacket and lighter trousers might look a little top-heavy. You also say to take care to ensure you have a polo with collars that won’t slip under your jacket lapel – a major problem, I think, as I love polos like this but struggle to find collars that do work (and have not splashed out on yours yet). But in the photo it looks like it has indeed slipped under the collar on one side at least. Finally, would you still tuck your polo in like this? I’m in two minds as to that look.


Thanks – interesting, I hadn’t thought of an overshirt but yes, that’s a very good idea.

I suppose I ask on the tucking in because it always feels very ‘fashiony’, and I think I remember you saying the same somewhere to that effect, but if it wasn’t for that association (fashion advertising, generally), it would be a no-brainer. Any form of knitwear tends to look so much neater tucked in than a shirt because even if you have a washboard stomach the buttons will always ripple in between each other to some extent. I find it increasingly irritating. Perhaps it’s simply time for me to cough up for a PS polo!

Regarding the impact of physique and grooming, I guess it struck me because you look notably more put together, confident, and stylish in today’s post with the Tailleur charcoal suit than you do in this post. It’s encouraging to think we can improve with age.


Sorry, I wasn’t very clear. Shirts have buttons and knitwear tends not to. The way the bottom of a crewneck, poloneck or polo lies when sitting especially is much neater than with a shirt, but then you tend to lack the collar structure up top. I increasingly want both!