Adam: Can you offer some advice on packing for traveling and extended holidays? I will be on a 10-week holiday in western Europe this late summer-fall. I am at a loss as to how many sport coats, shoes etc I should pack. I know that I will be able to do laundry, which helps with some trousers and shirts. Given your obvious propensity for rigor and depth, the type and degree of information I am looking for would be something like: Can you recommend a shoe that is suitable for traveling and walking through museums etc. a lot? Some days will be touristy, while others are less packed. How does one look cool, wear cool shoes and not wear down shoes or kill one’s feet? Trainers/converse just won’t do. (Other questions: how many shoes? Should I bring my polish kit?)

Wow, that’s a lot of questions Adam. Specific advice on what you should take would require more information though – on your taste, formality of dinners or evening events etc. But I can certainly pass on some advice.

First, once you’re away for more than two weeks it doesn’t matter how long you’re away for. The amount of clothes is the same. You just have to look after them better and wash more.

Next, the key to shoes and jackets is to take a range that is flexible and, together, will fit any situation. So, for jackets I would take something like: navy cashmere blazer, checked sports coat (in perhaps a pale grey ground) and a corduroy or Harrington jacket.

The idea is that the blazer would be smart enough for anything, bar the opera; and the corduroy would be rough enough for anything (walk home across a field from a country pub, perhaps). In between these two extremes, they provide variety. And they can be alternated during the day as well – donning the blazer for a nice dinner out, for example.

Three is also a good number for shoes. You need at least two, so they can be alternated every day, and three means they can also be changed in the evening if they’ve had heavy wear.

Again, you want to cover all your bases. So at one end, perhaps a smart pair of Oxford lace-ups in chocolate calf, at the other a pair of desert boots in biscuit suede, and in between something for variety – monk-straps, perhaps, or slip-ons for easy days at the hotel.

These will cover all eventualities unless you want to go running, hiking, to the beach or to a business meeting. Unless there are any formal evening events, you won’t need black shoes. And the desert boots will be rough and ready enough for that walk back from the pub.

As to your more specific questions, a good pair of well-fitting leather shoes should be the best thing to walk around in all day. Lace-ups support you better than slip-ons or boots. And you probably won’t need your shoe-polish kit. Just brush the shoes down every day after you’ve worn them and take at least one pair of travel shoe trees, to put in after you’ve brushed them.

Make good use of good dry cleaners and cobblers where you are staying, and give all of your clothes some love when you get back home.

Any more specific questions, let me know. And enjoy your trip!

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Great answer to an interesting question.

If a gentleman wants a pair of crepe-soled shoes that are comfortable, lightweight, and nice enough to wear with a jacket & tie, then I would suggest a dress shoe by Rockport. The non-leather sole means they are comfortable and watertight, and many of their shoes are light as a feather. They also have a full range of casual shoes.

They are not “permanent” shoes; the crepe sole will wear away and cannot be repaired or replaced. Then again, the same is true for athletic shoes, boat shoes, and many other kinds of casual shoe.

Full disclosure: I am a satisfied customer with no financial interest in this company.


I consider myself something of an expert on packing. My wife and I have done weeks in Europe and Asia with one carry-on each. Here are some thoughts.

1. Shoes-Cole Haan has licensed the Nike Air technology into a large number of “dressy” shoes. I have found two pairs that are comfortable for all day touring and walking but are good looking enough to wear to a smart lunch or dinner. The intergrated Nike Air technology is either hidden or subtle so there are no compromises. Take shoe trees of course to refresh the shoes and reduce odor and wetness each night.

2. Clothes – You haven’t described your schedule, but you only need enough clothes to prevent someone you know from seeing you in the same outfit twice. If you will be no more than three days in any one place, you can certainly get by with only four outfits (three pairs of pants, 4-5 shirts that match with all pants, and two light sport coats (one if you can be OK with it being in most of your holiday pix). Plan on doing regular washing or laundry.

3. Don’t forget your chargers. There are some great universal chargers for multiple electronic devices that will save weight and space.

4. Do not be tempted to bring cargo shorts or pants. They should be removed from your wardrobe. I also advise against bluejeans if you are a grown up. If you look like a tourist you will be a target of pickpockets. Many disagree with me on this, but when my wife and I travel, we are almost always approached by tourists for directions, with the tourists attempting to speak the local language to us. As a guest in a country, I want to look like I fit into the country.

5. If you are going to be staying in one place for an extended period, I strongly advise shipping most of your clothes to your hotel in advance, and then shipping them back when you leave. Travelling with no or very little luggage is a luxurious treat usually reserved for those with personal assistants.

Ah, every time I stop by your blog it is like a breath of fresh air, imagining the stylish men following your advice 🙂


Great insights Simon!

There is one thing I would juist like to add, which is that when packing lightly, a good pair of (dark and unwashed) jeans could be a great companion.

Jeans are pretty sturdy, go with about anything and can be dressed up or down. So when I don’t want to take too much with me, a good pair of jeans can be replacement to two or three pairs of trousers.


(Original Questioner Here)
Thanks for the great advice. I must admit, my question was untimely since I just arrived in London yesterday. I think I did ok by Mr. Crompton’s advice. Part of the catalyst (as it were) for my question was a dearth of information on the subject, which I think is part of the vision of this blog. Anyway, I’m off to the Paul Smith sale shop.

Thanks again Mr. Crompton and everyone else.


Easy and Elegant Life

I agree with kingjnod on the choice of the Nike Air tech shoes. I’ve got a pair of brown suede brogues that fit the bill for a long day of sightseeing. A little waterproofing spray makes sure they’re up to all conditions.

A pair of Belgian shoes lets me sail through security and double as very formal slippers for an evening out.

And I usually take a lightweight cashmere sweater, just in case.

Great advice and I know that Adam is going to enjoy his trip all the more for it.

Evan Rose

What kind of desert boots are those? They look great.