A few years ago, I wrote a piece detailing what I packed when I travelled – focused on Naples in wam weather, but with application to colder weather too. 

However this was a ‘work’ trip for me. One where I was expected to give a certain impression, and tailoring was pretty much obligatory. 

If anyone is travelling for work or just wants to be smarter, the advice in that article still stands. But today, given I’m going on holiday soon, I though I’d do a vacation-oriented alternative.

Now, even though I’m on holiday, I don’t want to be wearing a T-shirt and shorts every day. I will take that and I do wear that, but I like more elegant clothing too much to wear it the whole time. 

Also, family holidays involve a small amount of variation in location. Although we spend most of the time in a villa with a pool, we will also usually spend a couple of days in a city too. 

And personally I think that for reasons of both style and propriety, I want to dress differently in an urban restaurant than I do at the beach. Most tourists appear to disagree with me, but I like to think it’s just because no one has explained this kindly and carefully them. Or pointed out that none of the locals are wearing board shorts and flip-flops. 

So, the conditions that variously shape my holiday wardrobe are:

1. Heat. This is summer, and I’m travelling south. Temperatures 20 to 40 degrees celcius.
2. Variation of formality. Beach, villa, city; playing with kids, travelling, dining.
3. Space. We’re a family of five; no one can take too much.
4. Style. Whenever practicable, I prefer to dress a touch more elegantly. Never in a tailored jacket, but not always in a tee either. 

With all that in mind, this is what I will be packing this summer. 

Tops

The thing that satisfies condition number four more than anything else, is wearing collars. A polo shirt or a casual shirt, rather than a T-shirt. Still, at least one T-shirt is just practical, for example when getting hot, sandy and sticky at the beach. 

• White knitted polo shirt
  • or cream, eg PS Finest Polo
• Black knitted polo shirt
  • eg Perro cotton polo 
• White casual shirt
  • or pink, eg A&S linen shirt
• White T-shirt
  • eg PS Tapered T-shirt

Bottoms

The second thing that helps retain a little sartorial interest is wearing trousers rather than shorts. A loosely cut, openly woven linen trouser can be just as cool as a short, particularly with an elasticated waist. 

The colour scheme above also starts to make sense when you consider the bottoms. Pretty much every top can go with every bottom, creating a maximum number of combinations in a small suitcase. It feels kind of boring, but actually it stops me being bored.

• Olive linen trousers
  • eg Anthology drawstrings
• Sand linen trousers
  • eg Edward Sexton Hollywood tops
• Beige cotton shorts
  • eg PS shorts

Outerwear 

I’m unlikely to need much here given the temperature, but will need at least one jacket-like item for travelling and going out. And at least one sweater for the late evening or early morning.

The downside of polo shirts is that knitwear often doesn’t work well over them – or at least, the thicker they are and the more structured, the less it does so. Hence why cardigans are useful.

• Dark-brown linen overshirt/shirt-jacket
  • eg PS Overshirt
  • or casual alternative: jungle jacket
• Cream cotton/linen cardigan
  • eg RRL Arran-knit
• Perhaps, something long-sleeved that can be worn on its own
  • eg Rubato long-sleeved T-shirt. So nice – cool as a T-shirt, but looks like a sweater
  • A warmer alternative: Colhay’s cotton/cashmere crewneck. Good just on the skin

Shoes

Versatility here is of course of particular importance, given you need shoes that can be worn on the beach, loafing around, for dinner and for travelling.

• Black espadrilles
  • any brand, just hand-sewn
• Cream tennis shoes
  • eg beaten-up (derby-front) Doeks
  • or another colour for variation: yellow, pink
• Suede casual loafer
  • eg Alden LHS

Others

Apart from the obvious, like a pair of sunglasses, a straw hat, and a pair of swimming trunks, some extras to sneak in are:

• Vest 
  • Useful layering to deal with changing temperatures. Under a shirt, polo or sweater
• Neckerchief
  • Cotton, tied at the neck. Again warmth, but also for sweat
• More than one hat
  • A nice way to add variation. As well as the straw, perhaps a cap, perhaps a bucket hat. Can add colour to otherwise functional tonality
• Short pyjamas
  • I have a set from Schostal, with a short-sleeved top and shorts. Both can do double duty as normal clothes in a pinch. (Swim shorts can do that nicely too, if not too obviously for swimming)

This is not comprehensive, excluding things like bags for travelling and the beach (also, by the way, nice ways to add some interest and colour) for example.

But the main thing is dealing with all four of those conditions, which isn’t easy when there are two kids and a baby. This basic list has proved to be a fairly successful way for me to meet them, and not lose sartorial inspiration entirely. 

Tips and experiences from others, as ever, very much appreciated. 

Other pieces that may be useful:

• The dedicated category on summer dressing
• The video on packing a suitcase
• A more casual summer capsule
• And lastly, ‘holiday snaps’ articles from previous years