The Difference Between A Holiday Wardrobe And A Suitcase Full Of Regret

Why the clothes that look most “holiday” are often the ones you wear least — and what to pack instead.

Every holiday I have ever been on has taught me the same lesson, which is that I’m apparently not to be trusted near a suitcase.

At home, I’m fairly clear on who I am; I like simple clothes, I know the colours I wear, I understand, broadly, the amount of fabric I can handle before I start to feel like a decorative lampshade and I don’t tend to leave the house dressed as a woman who owns a villa in Hydra and says things like, “We’ll just take the boat round for lunch.”

And yet, the moment I start packing for a holiday, all self-knowledge appears to leave my body. Suddenly I’m holding up a dress I’ve never worn and thinking, “maybe this is who I am in Spain”. I start believing in complicated straps, I consider colours I wouldn’t wear to answer the door, I pack shoes that have never successfully completed a school run, let alone a cobbled walk to dinner and I develop a mysterious confidence in white linen, despite knowing full well that I am travelling with a child, SPF 50 and the general aura of someone who will be handed a melting ice cream within fifteen minutes of getting dressed.

The most memorable offender was a dress I packed for a family holiday because, in my head, it was going to be perfect for one of those easy, golden, “we’ll just wander down for dinner” evenings. You know the sort — salt in the hair, slightly bronzed shoulders, child behaving like a small European prince, husband relaxed and appreciative, everyone eating grilled fish under a tree.

In reality, the dress required a bra I hadn’t packed, a tan I didn’t have, a level of abdominal confidence I couln’t summon after a bowl of pasta, and a restaurant with absolutely no wind. It stayed in the suitcase all week, folded with its own quiet judgement, while I wore the same black dress three times and felt extremely relieved every time I put it on.

That, I think, is the difference between a holiday wardrobe and a suitcase full of regret.

The latter is packed for the woman you briefly become in the days before you go away. Whereas the holiday wardrobe is packed for the woman who will actually be there: hot, slightly tired, carrying sun cream, trying to find the room key, and wanting to feel chic without having to negotiate with her clothes.

And this is where packing so often goes wrong. We don’t pack for the itinerary, we pack for the moodboard. We pack for the woman in the saved folder, the one walking through a whitewashed village with damp hair and a basket bag, wearing a skirt that has never encountered a high chair, a snack wrapper or the faintly hostile lighting of an airport bathroom. We pack for the dinner that might happen, the beach club we may not go to, the boat trip that will involve less sun-dappled elegance and more wind, salt, wet towels and trying not to flash someone’s father-in-law.

We pack for an imaginary version of ourselves who doesn’t sweat, bloat, spill, burn, get tired, get irritated by bad lighting or regret a shoe by 8.04pm.

A holiday wardrobe, by contrast, is much less romantic in theory and much better in practice. It’s not a random collection of holiday pieces, it’s a small, intelligent ecosystem; everything earns its place, everything has a job. The pieces speak to each other, the sandals go with the dresses, the dress works with the swimwear, the shirt can be worn to breakfast, over a swimsuit, with trousers, with shorts, and possibly as emotional support when the air conditioning is aggressive.

There’s a colour palette, a shoe strategy and no panicked dress that requires a special bra, a perfect tan, a different body and a level of social commitment you don’tcurrently possess.

The best holiday wardrobes are usually quite boring on the bed and very chic in real life. A good black swimsuit, a white shirt, a linen trouser, a cotton dress, a flat sandal, a basket bag, a simple gold earring, a slip dress, a lightweight knit and a pair of sunglasses that make you feel expensive even when you are eating crisps from a packet on a sun lounger.

None of this sounds wildly thrilling but that is exactly the point.

The mistake is thinking that holiday clothes need to be more exciting than normal clothes. They don’t! They need to be easier, lighter, more comfortable, more repeatable, more forgiving, and more adaptable. They need to make you feel like yourself, only with better shoulders and a drink arriving shortly.

We’ve been sold the idea that holiday style requires reinvention. The “summer wardrobe”. The “vacation edit”. The “destination pieces”. Suddenly everyone is telling you that you need a crochet trouser, a shell necklace, a raffia platform, a printed co-ord, a sarong, a resort shirt, a beach-to-bar dress and something described as “sunset-ready”, which is marketing language for “you will wear this once, feel faintly overdressed at dinner, and then ignore it until next June”. But the women who look best on holiday rarely look like they bought a costume.

Jane Birkin in a white T-shirt and basket, Jackie O in black sunglasses and a headscarf, Carolyn Bessette-Kennedy in simple swimwear and a shirt, Carolyn Murphy in those old Ralph Lauren images, looking as though all she needs is salt water, good genetics and a pair of trousers cut by the gods. What those images all have in common isn’t novelty, it’s clarity.

The clothes don’t look like a break from the woman wearing them, they look like an extension of her. They are simpler, lighter, easier perhaps, but not suddenly from another planet. No one appears to have panicked near a resortwear rail. That’s the dream, really; not to have the most interesting suitcase, but to have the one that feels the least hysterical.

I used to think the best holiday wardrobe was the one with the most beautiful pieces. I now think it is the one with the fewest opportunities for regret.

The older I get, the less interested I am in packing for the fantasy of a holiday and the more interested I am in packing for the reality of one. The one with heat, walking, a child in tow, the dinner reservation, the swimsuit situation, the fact that linen behaves beautifully for approximately eight minutes before becoming a historical document. The need to feel like yourself, only slightly more rested and better lit. This is why the fantasy item is almost never the hero item.

The fantasy item is the printed dress you bought because someone in a campaign wore it barefoot on a terrace or the plain black dress you can wear with flat sandals, wet hair, gold hoops and no emotional admin. In short, the fantasy item is the thing you imagine being photographed in.

I have now developed a fairly reliable test for this, which is: would I wear it on the third night? Not the first night, when everyone still has enthusiasm and clean hair or the fantasy lunch, when the light is perfect and nobody has yet asked where the goggles are. The third night — the one where the suitcase has started to look faintly ransacked, your skin has entered its own relationship with sunscreen, and you want to look nice but not at the cost of your nervous system.

If the answer is no, it probably shouldn’t come. The third-night test is how you identify the clothes you actually trust. The dress you don’t have to think about, the shirt that works over swimwear and with trousers, the sandals that do not become a character-building exercise after 600 metres and the bag that fits sun cream, sunglasses, a room key, a snack for a child who denied being hungry fourteen seconds earlier, and still somehow looks chic.

These are rarely the most exciting things you pack. They are, however, the things that stop a holiday wardrobe becoming a costume department for a woman you invented late night whilst panic-scrolling resortwear on Pinterest.

The other test is: does it have friends? This sounds ridiculous, but it’s possibly the most important packing question. An item can be beautiful, but if it goes with nothing else in the suitcase, it’s not a holiday piece, it’s a hostage situation. It demands its own shoes, its own bag, its own underwear, its own weather conditions and, sometimes, its own personality.

A holiday wardrobe works when everything has friends — the white shirt is friends with the swimsuit, the trousers, the shorts and the slip dress. The sandals are friends with every hemline. The basket bag is friends with breakfast, beach and dinner. The black dress is friends with flat sandals, gold jewellery, slick hair, damp hair, a tan, no tan, tiredness and one more glass of wine.

A suitcase full of regret is full of items that refuse to socialise. There’s always one dress that only works with one shoe, one top that needs the bra you forgot, one skirt that looks good standing still but becomes a legal issue when it’s windy and the one heel packed for a restaurant that turns out to be down a hill, across cobbles and through the sort of charming old town that was obviously designed before anyone cared about ankle stability.

The problem isn’t that any of these things are wrong, it’s just that they ask too much of you and, personally, on holiday, I want my clothes to ask very little of me.

This is the real luxury of a good holiday wardrobe — not designer labels or a different look for every imagined moment. It’s ease and being able to get dressed after a shower, with damp hair and slightly sun-warm skin, without trying on six things and ending up cross. It;s knowing that the dress works, the sandal works, the bag works and your feet are not filing a complaint.

Of course, this does not mean holiday dressing should be joyless, quite the opposite. A good holiday wardrobe should make you feel better than your normal clothes, not less like yourself. It should have a little lift, a little romance, a little “I am away, please don’t email me unless something is on fire”. But it should be rooted in who you already are.

If you don’t wear colour at home, you probably won’t suddenly feel effortless in a tangerine maxi dress because there’s bougainvillaea nearby. If you don’t like fussy clothes in London, you won’t love fussy clothes in Mallorca, where you’re hotter and holding more objects. If you never wear heels, don’t pack heels because a restaurant has tablecloths — tablecloths don’t require arch pain.

Your holiday wardrobe should stretch you gently, not abduct you.

The point is not to become a new woman, it’s to become a more relaxed version of the existing one and perhaps that’s why packing is more emotional than we admit. A suitcase is not just clothes, it’s expectation, hope and who we think we might be if we were rested, glowing, away from normal life and briefly not responsible for the dishwasher.

No wonder we make strange decisions. But the most stylish holiday wardrobes aren’t built on reinvention, they’re built on recognition. Recognition of your body, your habits, tolerance for discomfort, your actual plans, real shoes and tendency to overheat. So before you pack for your next holiday, don’t ask, “What would a woman on holiday wear?” Ask, “What would I wear if I wanted to feel comfortable, attractive, unbothered and like myself, but better lit?” THAT is the sweet spot.

The holiday wardrobe isn’t the one with the most interesting piece, it’s the one that lets you get dressed without negotiation and one where the swimsuit works with the shirt, the shirt works with the trousers, the trousers work with the sandals, etc etc.

The suitcase full of regret is packed for a fantasy and the holiday wardrobe is packed for a life you might actually enjoy living.