Packing for travelling between seasons: cold then hot

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When I travelled to Thailand last month, I had a slightly different packing challenge to usual: in London it was eight degrees (celsius) with cold drizzle; in Bangkok it was 30 degrees and balmy. 

Now I wouldn’t be outside in the UK that long on the way to the airport, but it would be long enough. And I didn’t want to be that guy walking to the airport wearing a Hawaiian shirt and a panama in winter. 

Another wrinkle was that I had less room in my suitcase than usual, because I was carrying stock to give to the guys at Decorum. I had to be even more efficient with my packing. 

In terms of occasions, I needed clothes to host an event for readers, something else smart for visits and dinners, and perhaps more relaxed clothes for a day off and travel. 

My first thought was to find some way to combine clothes for colder and warmer weather, but in similar colour palettes so everything was interchangeable. This would allow me to swap things during the journey, and create other combinations when the need arose. 

So I went with a white/black/olive colour combination, and the smart version of that (pictured above) was:

  • PS olive linen overshirt
  • Thom Sweeney cream knitted-cotton T-shirt
  • Black linen trousers from Whitcomb & Shaftesbury 
  • Black Piccadilly loafers from Edward Green

This was nice in the Thai heat (though it was, apparently, cool for the time of year) and did well for walking around shops and galleries, as well as for a couple of relatively casual dinners with the team. 

I would normally have worn Sagan shoes from Baudoin & Lange with this kind of outfit, but the Piccadilly loafers were able to bridge this outfit and my evening suit. 

Then there was a more casual and warmer option, in basically the same colours. This (pictured above) comprised:

The advantage of everything being interchangeable was seen at various points when I swapped the field jacket for the linen overshirt, for example, but kept everything else the same. And swapped the boat shoes for black loafers in the evening, so it was a little smarter. 

For travel from the UK, I wore this outfit but with a grey PS Cashmere Rugby underneath the field jacket. This was warm enough, and the Rugby was nice on the long flight. 

I also wore a PS watch cap (black) and an Arran scarf (charcoal), both of which could easily be removed once I was in the airport. Things that can be easily removed like this are the best for transitioning between temperatures. 

The Rugby, in the same way, was removed and hung around the shoulders once I arrived in Thailand. The field jacket was of course perfect for travel, with all its multifarious and poppered pockets. 

You can see these various pieces in the picture above - the standard one readers will now be used to of everything laid out on my bed. It’s useful for these articles, but it’s also how my brain works through the various combinations. 

The only change I made (there’s always one, always last minute) was taking the field jacket instead of the Anderson & Sheppard chore coat you can see here. This was the right choice I think - the A&S one was wool and would have been too hot, even if it would have been nice to have another colour to play with.

Oh, and the grey cashmere crewneck was swapped for the Rugby. The grey work shirt you can see at the top and the olive Dartmoor on the right were alternatives to wear with the brown suit.

The black alligator loafers (vintage Polo) were what I ended up wearing with that suit, but could also have been worn the other pairs of trousers. This is always a nice thing to have - if you’re tired and on your feet all day, it’s nice to be able to swap shoes in the evening, or avoid wearing the same shoes two days in a row.

The suit is a new one from Cifonelli in a superfine wool. I’ve never really had anything in a superfine, and indeed recommend against it for readers that are just starting out. But I decided to try this as an experiment.

I’ll cover it at a later date, when I’ve put it through its paces.

The other things pictured or shown on the bed are:

  • Brown linen shirt from D’Avino
  • Vintage gold-rolled Caravan sunglasses
  • Clan Milano sunglasses, via Connolly
  • Vintage silver navajo cuff
  • White handkerchief from Trunk

In terms of bags I used my normal Rimowa check-in case and carried a Connolly 48-hour bag for the journey, which fits very pleasingly over the suitcase’s handle. 

Having deposited the linen overshirts with Decorum, I wore a super-soft old Big Mac denim shirt on the way home, having bought it at the vintage shop Wooden Submarine during our shopping trip on the Sunday. 

Nice to have the change, and nice to have the half-empty suitcase.

Thank you to the Decorum team for everything - the event we held, and my reflections on my short time in Thailand in general, have been covered here

The PS Linen Overshirts were with Decorum in Bangkok and are now in the Singapore store, to allow customers to pre-order them ahead of our delivery in March. Anyone local, do pop in and have a look. 

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Arthur

Hi Simon, will there be a restock of the olive overshirt this year? Really like the look of it. Cheers

Steven

Oh yay! I thought I’d seen you comment elsewhere that the olive wouldn’t be restocked and I was a tad disappointed. It’s a really nice colour and weight for this sort of ‘escape from northern hemisphere winter’ trip.

David

Do you think the olive will pair well with brown linen trousers, ecru and indigo jeans? Thanks

Alexander

Will the timing of the small topup be mentioned in the February product update, or is this expected earlier such that I should be keeping an eye on the shop ? Many thanks.

Alexander

Dear Simon. Will you be doing a re-run of the linen overshirts closer to summer, and when will you be doing an article summarising product updates for the year more generally? Many thanks.

Alexander

Splendid. The olive overshirt looks fantastic in these pictures. And always look forward to your product updates.

Anon

The black linen trouser from W&S
Do you remember the cloth bunch?

Anon

Yes, please do

Alexander

Also, could you provide any further details on the style of the trousers please? I know you have a few W&S trousers and may have covered this elsewhere apologies.

Anon

Many Thanks

Alexander

1) I applaud you for managing to travel with a superfine wool suit. Did you have to deal with heavy creasing and if yes, how?
2) What happened to the hem of the bryceland’s jeans, if I may ask? On a similar topic: I really tried hard not to get any grey creases after washing my black bryceland’s jeans, removed the jeans immediately after a low spin. But the creases came nontheless on the side down where the wet and heavy jeans make a fold while hanging on the clothesline. The wet jeans are too heavy to hang them on the belt loops. Any special tip on how you hang dry your jeans to prevent this? Thanks

Alexander

Nice. I have the same marks on my buzz rickson chinos after leeting down the hems a few weeks ago. Seems like a lot of people now want their casual trousers just a tiny bit longer again. Although the trend I see on IG with a clear break or even stacking up at the shoes (guys from the Anthology etc.) is not for me.

Steven

Y’all are showing your youth. Having grown up in the 1970s (bell bottoms and platform shoes) I’ve always thought trousers with no break look too short. Which goes to show how elements from the era we grow up in stick even as the overall trends change out from underneath us.

Anonymous

Hi Simon
Surprised to read the word balmy when describing the climate in Bangkok. I used to travel there regularly on business and humidity was my enemy. Everything was slightly damp. Having to wear a suit and tie was horrible, even if the cloth was the best of Fresco. You can understand the habit of wearing a vest under your shirt.
Which airline/class of travel did you use? Wearing a cashmere rugby on board an aircraft would be too warm for me but I can understand it from a comfort viewpoint.
Thanks!

Antony

What are the reasons you don’t wear bryceland jeans with tailoring?

In addition, would a narrow leg opening go better with tailoring?

Antony

2) I had them hemmed a little too short, so let down the hems, and now I rather like that slightly ragged look. Helps that I don’t wear those ones much with tailoring.

Sorry I understood the above text you wrote as you are not wearing the jeans often with the tailoring.

I saw ango Italian jeans have narrow openings and they think that suits well with the tailoring.

Antony

Interesting, thanks for the clarification

Stephen

Useful. Good to see I’m not the only one who takes two pairs of sunglasses when travelling!

David Smith

On another subject Simon, I’ve recently placed an order with Charlie Borrow for a pilot bag as featured in a previous article on your site . Having visited Charlie at his shop in Shoreditch and decided on a few customised additions to the bag ( Charlie couldn’t have been more helpful & is a really nice guy ) I just wanted to thank you as without reading the article I would never have know about Charlie or his work . Looking forward to collecting my bag later this month. Thank you once again.
All the very best for 2025

Raj

Definitely challenging, my first thoughts would be to use a preppy base for my casual clothes that style can lend it self to layering quite well, having a few nice shirts in which the sleeves can be rolled and also some light blazers and having quite few Ralph Lauren pieces on your holiday illustrates this and I suppose suits work incredibly well as well , even in places warmer parts of Italy a suit is a staple amongst men as even in hotter climates it can still keep you cool.

Just out of curiosity you said, you said you were in Thailand did you check out some of the local tailors out there , obviously there selection and skill may not match more well established brands with a prestigious reputation ie Savile Row and Italian tailors, but it would be interesting to check it out from a journalistic perspective at something that might be at the budget end of the market.

Winot

I’m interested in your luggage choice. Could you explain what made you choose the Connolly 48 hour bag over the Bennett Winch SC Holdall? Thanks.

Zawaad

Hi Simon! Would there perhaps be a chance of having a XXL in stock for the linen overshirt this time around? I have the XL in the navy I picked up last year and although I do love it, I find it fits more like a regular shirt, so it’s just fitted and has less room to layer underneath. Something a bit fuller would be lovely. Cheers and happy new year!

MS

M65.in Thailand was an interesting choice. Were you at all concerned about the connotations of such an iconic piece of clothing which is so intrinsically linked with western military intervention in that part of the world? I own one myself but make a point of not wearing it around my Vietnamese in-laws, it just seems insensitive. Perhaps Thailand, despite undoubtedly being SE Asia, was far enough removed from the conflict that made the jacket so iconic that it doesn’t have the same connotations.

Mark G

Ironically, I was in Thailand myself in November to early December, I think I missed you by about a week. Not only did I have a similar challenge coming from New York but I actually had several meetings in NYC and went directly to the airport from them. I didn’t need quite as much formality as you, which helped. I wore a tropical weight navy blazer and dress trousers to my NYC meetings and Alden cordovan full strap loafers. While more like summer business casual, no one really noticed. I travel quite a bit to Asia and Latin America for business during the US winter. I have two pieces of advice: first, always pack/dress for the destination, even if it means a little discomfort until you’re in the airport. (And you are usually indoors or in cars, taxis, or similar most of the time anyway.) Second, the two items I ALWAYS have, winter, spring, summer, and fall, are a scarf (thanks to you) and a packable down vest. Even when traveling in the US summer to a tropical location, you can never be sure of the temperature in the plane, lounges, etc. Or you can pack it into its pocket and use it as a pillow. On my rather chilly day of NYC meetings prior to heading to the airport, I’d wear my vest and scarf under the summer weight jacket. It might have looked a little silly — or like a tech bro — but I don’t think anyone really noticed. And I’d fold them up into my (Permanent Style – Frank Clegg) tote bag when I got to the lobby of my meeting locations. When I finished, I essentially had exactly the wardrobe I needed for the balmy weather of Bangkok and Singapore.

R

Hi Simon,

Have you considered doing a review of your Rimowa luggage? I know you did a couple when you were using Globetrotter for travel. Would be interesting to talk about your experience and why you made the switch. Would also be of interest to me because I am considering upgrading my luggage from Samsonite (which I have been using since my early 20s) to a brand like Rimowa or Globetrotter or Tumi.

Cheers!

Anonymous

Briggs and Riley offer Tumi quality for much less. And their bags are built to last.

A

I have used a Rimowa classic for 8 years and wouldn’t unreservedly recommend. In particular with todays LVMH markup. I got my medium sized checkin luggage for ~ 570€. Today it would be double that.
Contrary to the reputation, Rimowa aluminium luggage is not indestructible. They do get a lot of dent’s, which could be seen as patina and quite attractive if they held forever. Mine got a hole in the skin, which is thin but doesn’t flex much, thus is at a higher risk of piercing compared to something more flexible like polycarbonate. I banged the sharp edges with a rubber hammer, glued a piece of wood on the inside and put silver tape on the outside. At least it is now easy to identify at the airport. Then the screws from the top handle came loose which I fixed with loctite. It is also unnecessarily heavy, like all aluminium luggage. But the wheels are nice, and it did look nice from a distance. Up close, you see the telescopic handle is an ugly brown plastic trying to imitate leather.
If you need check-in luggage for clothing, I’d suggest polycarbonate or nylon. Higher ranges of Samsonite are then as nice as Rimowa, except perhaps, the wheels. I’d also stay away from anything unnecessarily heavy. It is impractical when a cabin trolley weighs 4-5kg and the allowance is 8kg. In economy class, my cabin trolley got weighed on two occasions the last years. And yes, they did force me to gate check-in the time it was over 8kg. If you really do need something robust, then I’d look in the direction of Peli and similar cases, but again not Rimowa.

joners

Simon,

In the UK, do you think one could wear linen suit for most of the year, given appropriate outerwear is observed?
I have wondered about this for a while

Paris

Hi Simon – I am heading to Yorkshire on a holiday in a few weeks, and I wondered if you are aware of any mills/fabric stores that are open to the public to visit? I believe – for example – that Lafayette Saltiel Drapiers in Paris is open for the public to go and take a look, is there anything similar in Yorkshire?

Thank you

MB2468

Hey Simon, would you be able to tell me more details about your a&s wool chore? Is it made of heavy wool, suitable more as an outdoor piece?

Dan James

Thank you for this article Simon.
I often find myself going from North East Asia to South East and in winter it’s always a challenge to get the balance right. I must admit to standing on a freezing platform in Japan in just a linen shirt after returning from the Philippines-not a wise choice but at least the wait wasn’t so long. Layovers in the Middle East can offer the same challenges and so keeping my Finest Crewneck in my carryon helps with the flights especially those at night.

Dartmoor enthusiast

Hi Simon,
Are you planning on re-stocking the Dartmoor in the olive color? I missed out on getting one in L and it would be great to get one in the updated fit.

Kenneth

Another good article…Simon Crompton means Globetrotter..everyone enjoy your week….cheers and much peace..

Dario

I went back in October to Sicily. Even if it was 4 degrees in Copenhagen at the time I had to go to the airport, I just dressed and packed for the destination. And in the metro to the airport I could see that most people were doing the same (in regards to dress of course, didn’t open their suitcases).

Gab

Hi Simon, woud you care sharing where this grey shirt came from?