How to pack for a three-day trip: Video

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The 'travel capsule' posts we've done are always popular - I think because they are useful for actual travel, but also for anyone looking to build a versatile wardrobe in general. In that way they're one more addition to the 'wardrobe building' series.

So I thought it would be nice to do one or two of these as videos, to show the clothes myself and to walk through how I saw everything going together - how to get the maximum number of outfits from the minimum number of clothes (presuming that's in some way your aim).

This is the first of two videos, suggesting clothes for a three-day trip - basically wearing one outfit and packing another, but with every piece interchangeable. The second video expands on this to create a set for a seven-day trip.

Thanks to Globe-Trotter for lending us their space upstairs in the lovely Burlington Arcade store.



For other examples of travel articles, see:

The clothes shown are listed at the end of the video. If you need any more details, do ask below

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Lindsay McKee

Simon, this is the post I need right now. I’m generally prone to over packing!
It’s always a thrill to see one more article added to the “Wardrobe Building Series”.


Hi Simon, which tweed jacket are you wearing? Cheers


Thank you. It’s a rather good type of video for showing off the jacket because you’re moving a little – which brings the jacket to life much more than static photos – but you’re not moving so much that one loses the detail of the cloth’s texture, the shape of the shoulders etc.

Lindsay McKee

Can you tell me a bit more on the serge trousersfrom W&S and the cloth bunch please?

Lindsay McKee

Thanks again

Robert M

Short and sweet, very nice!


Words you wouldn’t want to hear from a woman.


That carry-on suitcase is gorgeous! How’d you compare it to the Rimowa carry-ons in terms of durability?

Il Pennacchio

This may be a holdover from my backpacking days, but I try not to travel with jeans. They’re heavy and take a very long time to dry once wet, be it from rain or laundry. On more than one occasion, I saw someone at the hostel throw damp jeans into their bag because they had a train or flight to catch.

Il Pennacchio

True that. The first time I traveled with tailoring, I had to get new luggage because stuffing a suit into a 35L Cotopaxi wasn’t going to cut it.


Hi Simon, are those jeans left hand twill denim from Brcyeland? They look new. Cheers.


Are these the 133s? If so, i also just got a pair. Am liking them so far!
Have you covered ever how to manage the fading on a pair of denim? These brycelands are the first pair of Ive ever gotten essentially brand new, while all my other jeans are either a washed style or vintage and have already come worn / faded / distressed to taste.
So advice on getting some nice fades (something about the frequency of washing right?) and then your thoughts on if the fading changes a pair of dark indigo in terms of formality or “look” would be appreciated.
Almost all photos of menswear guys online either show new looking jeans or a washed style, but i cant remember seeing a photo of a dark indigo pair (like a drakes or brycelands model) worn out in the wild but with obvious wear and fading.


Well-produced, informative and a subject that is important and not always easy. I think your recommendations are sound. The only thing that surprised me was the odd navy tailored trousers. I think that grey is more easy to combine with other stuff than navy trousers. I get that grey trousers could be a problem if they were to similar in light/dark than the herringbone sport coat.


How about replacing them with some brown or other earth tone (khaki, beige, tan, darker olive) pant in a less formal make, like a workwear chino (brycelands or armoury) or dress chino (rubato). Less formal for me, personally, as my line of work / style wouldn’t require tailored trousers, but it still is chic for personal and business. Thoughts?


I just wanted to say I like the video production. I think it captured the sense of personal advice and professionalism, which I think of when reading the blog. Not youtuber-in-his-bedroom but also not impersonal network television. 🙂


Hi Simon,

Thanks for the video. I’m curious about the trousers, since I would expect navy trousers to not be as practical as grey and with the possibility of them looking like an orphan piece of a suit. What makes them work as separates and in which other situations would you say navy trousers work?

Thank you


Nice video. I may have misremembered this, but I thought you weren’t keen on dark trousers with a grey jacket. Am I completely wrong or have I got the wrong nuance on what you said?


Thanks Simon – apologies, I was confusing my recollection of the navy trouser article you have cited, and the appeal to you of cream coloured trousers (“this feels like me” article) or grey.

Max Alexander

I don’t feel I need everything to work together for a 2-night trip—it’s enough to have one smart and one casual outfit. Thus I’d sub the suede loafers for trainers. And as others have noted, jeans are heavy to pack and slow to dry should they get wet; I’d switch them for khaki chinos. That all said, I confess to checking a full-size bag even on pretty short trips, especially in winter which allows a broader range of footwear and outer wear.


Simon, do you use shoe trees when you travel? I have always done so but finding they add quite a bit of weight.

Would it be worth picking up some travel shoe trees (light plastic) and if so can you recommend a source?




Simon what would you suggest wearing if you want to travel using a budget carrier like Wizz and can only take a tiny laptop bag with you to avoid paying the £50 luggage add on? The key is what you wear onto the plane, so would you say wear jeans, then a T shirt, jumper, jacket, coat? Any other suggestions?


Yes its not so much packing advice as carrying on your person your intended wardrobe) You see I need to travel short haul by Wizz quite frequently and the extra £100-120 for luggage adds up over time. Ive seen it done to ridiculous extremes and whilst Im slightly embarrassed going the whole hog I’d be prepared to go some of the way) I think a couple of T shirts, jumper, a coat & putting a pair of spare shoes in the bag could work. Im also toying with the idea of mailing some of my wardrobe by post to my accommodation at the other end and then mailing it back again before return.


Exactly. I just feel bad for anyone sitting next to me as Ill be like the Hulk with all my layers on 😉


I travel to Italy to visit family a couple of times a year for around 4-5 days and refuse to pay Ryanair’s luggage surcharge (that’s money I could save towards a clothing purchase!). With a slightly bigger bag than a laptop bag (but still small enough to fit under the seat in front of me) I can fit in 3 spare shirts and a spare pair of trousers. If I wear a jacket and a thin intermediate layer like a cardigan or jumper while travelling, that gives me nearly as many options as what Simon has packed in this video. The only thing I forego is a spare pair of shoes.


Extremely satisfying. 😎


Really enjoyed the video. I travel a lot so very interesting to see what you would pack, Simon.
For me, the major missing items are: (i) toiletries; and (ii) running/gym kit. The former need not take up much space but some of us need quite a bit to keep ourselves looking pretty. The biggest challenge with the second is trainers, which can take up a lot of room. I deal with that by swapping out one pair of shoes.
Both of the above much helped by travelling with an added tote that meets airline ‘personal item’ dimensions.


What is the reason for choosing Piccadilly instead of your unlined Dover? I think Dover should be more comfy and versatile. Also what is the shirt you’ve worn Simon? It looks fantastic with angled cuffs. Cheers.


Simon, what do you recommend for luggage these days at various price points, both for carry-ons and checked luggage? Maybe the subject for a future article? With luggage, it seems hard to balance style, utility, and price, especially because there just seem to be fewer options for luggage than there are for, eg, shirts. Your guidance would be very helpful.


I theorize that a shetland submariner could be all-occasional for the midwest and esat coast weather in the states. I am gonna try it out this weekend with a four layer setup: merino layer, PS oxford, the submariner, and a covert coat. Might seem rather clumsy, we’ll see.


Hi Simon, it occurs to me that, for even greater versatility, instead of the shawl-collar cardigan one might opt for a piece that can more easily fit under the jacket – do you think anything could work well here both as a stand-alone outer layer and under the jacket?

Peter Hall

I do plenty of short business trips. One factor which has decreased packing(post covid) is the need to step off the aircraft and be ‘meeting ready’ .

Tweed has certainly come into its own as a travel jacket. I actually take more smart/casual evening wear as so much business is now conducted in a less formal environment. I would swap out the shawl for another wool jacket, but these are my circumstances.

I will add that warm weather business packing is more challenging!

John Doe

Nice video! Being that I’m green to this website, I haven’t heard you talk, Simon. For some reason I was expecting a Nordic/Scandinavian accent even though I know you live in England. Cheers.
-Finnish American


As someone who spends a lot of time in planes and airports, I keep wavering between wanting to wear the favourite clothes I am bringing with me because airports are places where you see and are seen by a lot of people, and needing to wear my least favourite clothes because I wouldn’t mind them getting dirty, frumpy and possibly damaged during the trip. Still not sure how to resolve this quandary. Any advice, Simon?


Simon, I’ll have to grumble about the white sweater. In any other color, dyed wool works (Kelly green, navy blue, scarlet, etc.), but if you desire a white sweater, I think it’s best to go with natural, undyed, even unscoured, thus off-white wool. As it was on the sheep, minus the bits of straw. By contrast, a bright white (thus obviously dyed white) sweater just looks odd, as if somewhere along the line, someone felt the beautiful natural off-white of the sheep’s wool was unsatisfactory!


Ah, interesting. I guess it’s because I’ve never worn cashmere that I was mistaken about what I was looking at.
By the way, on the topic of sweaters… I’m sure you’re familiar with Inis Meáin. Any thoughts on them? Years back, I came across one at a nicer thrift store for just $35. Probably about a tenth of the original price. It’s very nice. Probably the lightest weight sweater I own, but I don’t know that it merits the original price tag. Their marketing/ website is very appealing anyhow.

Rowan Morrison

Do you think a sand flannel trouser would work as a substitute for the navy tailored trouser?
Never been a big fan of smart, navy trousers for some reason, perhaps because they won’t work with a navy jacket?
But the sand flannels will obviously work with the grey jacket – and might also look good with the cream cardigan and white shirts as it will all be slightly different tones of white? (with the look broken up with a brown belt and shoes of course).


Simon what do you think of the look where someone wears a suit but no tie? The suit and dress shirt can look perfectly fitted, but to me, it looks like something is missing still.


Simon are those suede loafers lined or unlined? And is there a benefit to either option for light travel?


Cheers Simon, your linked article has all the info I was after.


Would it be okay to wear flannel trousers when travelling?


Thank you for your prompt response. Hmm, it may not be the ideal choice for me. I have a couple of cavalry twill trousers which are obviously first-rate at holding up their shape. The downside is they often look too sharp for my outfits. Perhaps I should get a pair of serge trousers similar to yours. I’ve found some options from Dugdale. Should I go for them?


Any other suggestions on an ideal pair of trousers which would not bag at the knee when travelling?