There is no such thing as a perfect holiday wardrobe, but I still spend considerable amounts of time every year trying to put one together. There is something so seductive about a well-curated set of items for a week or two. It’s difficult to get one’s entire life right, but surely one can nail that trip to Sicily! Or at least the clothes!

I have been particularly guilty of this mode of thinking this summer, as I’m preparing for a short stay in Greece. This process has, however, very clearly reminded me of what I already knew about (very) warm-weather dressing: that it’s not about trends or brands, but about finding comfortable, flattering clothes that work well for you.

You could of course say that this is true for every kind of dressing, but I believe it’s particularly true in summer. If you live in a cold climate most of the time, it can be difficult to imagine what 30+ degrees actually means, so people buy clothes for imaginary scenarios where they don’t sweat or wind doesn’t lift off that huge sun hat that does indeed look absolutely stunning – when not in flight. There is something slightly ridiculous about wearing very trendy or very elaborate things in the heat. Don’t get me wrong, if you can pull it off, I salute you. For me, it just requires more effort than I’m willing to put in most of the time (although trends are of course not created equal in this regard and neither are the holidays).

The bottom line is, it’s worth taking the extra time to find these really nice shorts that are the right length for you or those cool sandals that don’t rub, because chances are they are what you’ll want to wear for years to come. And there is absolutely no need to replace those items every year, as the main building blocks of a holiday wardrobe are relatively timeless and many of said blocks will actually look better with age. When putting this list together, I found a post from seven years ago – and there isn’t nothing there I wouldn’t gladly wear now.

Because I’ve spent way too much time thinking about Ultimate Holiday Essentials in recent weeks, I decided to share a list of things with you that I would (and actually will, in a few days) pack for a stay in warm weather. If you’ve been here before, you know I don’t mean this in a serious or, god forbid, prescriptive way. I just enjoy reading these lists myself and perhaps it’s the same with you. So here we go, things to take:

A tank top. This is of course a classic, but it’s also a more trend-led item than most on this list. Ten years ago, it would probably have been a camisole covering the same spot and a couple of years ago a strong-shoulder T-shirt a la Frankie Shop (I’m still bringing one, in fact…). Classics have trends too and tank tops are very in at the moment. Case in point: all Scandi influencers wearing the Loewe tank top. But let’s not get discouraged by this, I have been wearing my Toteme tanks – I have a black and white each – on repeat. They are expensive, but also pretty much perfect. In addition to this, I have just bought a black and a white cropped version from Zara (they were sold out everywhere else) for six euros and am happy with these, too. I suspect I will pack all of them: they take little space and work well with everything. When choosing the exact shape, consider how comfortable you are not wearing a bra (I’m a strong 9 on a 1-10 scale).

A linen shirt. I dare you to find an influencer capsule wardrobe for summer that doesn’t include a linen shirt. And I’m not arguing. Linen is a great fabric for this season and the wrinkles that drive some people crazy really do not bother me on holiday. In fact, a good beach shirt should be a bit rumpled and not crisp and rigid. White is a traditional choice, but there are many good options. I have a pale-blue-and-white stripy one and a cornflower blue version. Both are oversized and can be used as a beach cover-up, as again every influencer will tell you. But they DO look excellent over bikini.

Something short. If you are somewhere really hot, chances are you’ll mostly want to wear as little as possible. Whether you prefer a mini skirt or shorts is a question of preference (and some people will of course prefer not to wear anything short at all) – I will pack both. I have a cheap Zara dupe for this Isabel Marant skirt, which I’m finding an excellent shape for warm-weather wear: short but not tight and rather flattering. I also have a pair of comfortable white shorts and have ordered this very basic beige pair from H&M. In the holiday context, I would always go for linen or cotton shorts with an elasticated waistband and in addition to solid colours, I think stripes work really well here (you could go for a coordinated set with a shirt to maximise your options).

Denim shorts. Now, this is the best example of an item where I would pay little attention to trends and a lot of attention to whatever works best for your body. Denim shorts can be a surprisingly difficult category if you aren’t a genetically blessed 19-year-old. But if you DO find a good pair, it is a great staple to have. They give a bit more structure, a bit more of a look than the non-denim kind I mentioned above, which can veer into basic pyjama territory if you are not careful. I have this soft and comfortable pair from Frame, but you absolutely do not need to pay this kind of money for good shorts. In fact, most of the categories here don’t require much spending and sometimes the cheaper options are superior to the expensive ones (I will return to this point soon).

Comfy trousers. I have an old pair of casual, cropped silk trousers that have seen me through seven summers or so. This time I forgot to pack them, so my new favourites in this category are these Massimo Dutti linen and cotton trousers that I have been wearing non-stop. They are a bit too heavy/dark for hotter climates, but the vibe is just right – slouchy, comfortable, not trying too hard. White wide-leg linen trousers are a very popular option for a reason, as they work well with many things, including a tan.  If this seems too predictable, you could go for silk in gorgeous colours and patterns – some pyjama vibes are allowed here, if balanced out by glamour.

A lightweight dress. This is probably the broadest category of the whole list, as it doesn’t matter if the dress is long or short, colourful or neutral, revealing or modest, as long as it’s easy to throw on and doesn’t cling to your sweaty body. So err on the side of roomy, although a slip dress with a bit of breathing room could work very nicely.  A white dress is lovely (and extremely on-trend, too), but so are brights and patterns. I would perhaps steer clear of black here, we will have a dedicated section on that next. I have to say that I don’t in fact have the perfect dress in this category – my tie-die dress (the one I’m wearing in the post from seven years ago) comes close, but that’s another item that I left behind. This is also the perfect moment to present the proof that pricy things aren’t always best suited for summer holidays, even if they are great. I have a wonderful Agua Bendita dress – it’s a gorgeous blue colour, very good quality and I look good in it. But I took it on a trip only once, because it is made of extremely high-quality linen and is fully lined, which means it’s heavy. It is also difficult to walk in (all that fabric!) and takes a lot of room in the suitcase. I paid around 600 euros for this dress. I cannot remember exactly, but I suspect I paid no more than 30 euros for my tie-die dress from Lindex. This is not meant as an endorsement of fast fashion, but there are now many smaller brands that do relaxed, sustainable clothes at reasonable prices. And in my defence, I bought my Lindex dress seven years ago and have worn it every summer since.

A black dress. I LOVE black in summer. In my view, there is nothing chicer and where I live, it’s also entirely possible to wear it throughout most of the summer months. If you are somewhere really warm, though, I would keep black for evenings. It is pretty much guaranteed to look elegant, especially if you pick a long body-skimming style or a nineties-inspired LBD. Some gold jewellery wouldn’t hurt either. My own version is this Sleeper dress that is perhaps less elegant and more dramatic (it’s interesting how it looks so innocent in white and has a completely different vibe in black). Still, I feel it has the chic factor and once you put it on, you need to do very little else to have an effective look. 

A kaftan/kimono. If there is one problem with my lived-in, well-loved summer style, it’s that it can be a little boring. All these classic items and neutrals and tan accessories… There are, of course, completely different ways of doing holiday style – crisp and preppy or glamorous and old school are just two options (and you can rather easily adjust my list to work for these styles, too). It’s just that I have found more demanding styles too… demanding. Keeping your pleated white shorts pristine and crease-free or wearing a Dolce & Gabbana dress with perfect make-up just seems too much effort for me in the heat. But I do crave something more than faded linen on occasion and this is where kaftans and kimonos come in. While you can do both in an understated way (I really like SU kaftans, for example), they are very easy to glam up without losing the comfort factor. You could, for example, go for the jewel tones of Tanel Veenre kaftans (I have the black one, I admit) or the glamour of the Riina Põldroos kimonos (all silk).

A cashmere sweater. If you have followed my blog, you know I am a cashmere super fan and I take a sweater with me everywherewhere, including in the summer. Even in places where the temperature never drops below 30 degrees Celsius, you may encounter an aggressive AC or need to visit the ice cream isle in a supermarket. ALWAYS BRING A SWEATER. I tended to gravitate towards white or stripy versions in the summer, but I recently saw Anouk Yve recommend colourful cashmere for one’s vacation wardrobe and she is absolutely right (she’s also a great person to follow on Instagram if you like simple and casual style with an elegant spin). Especially if most of your other clothes are neutral, a turquoise, orange or yellow sweater adds a really nice splash of colour. Just go for a lighter-weight version and you will thank me. (Merino is a lovely alternative if cashmere is not in your budget. But for example Uniqlo does decently-priced cashmere and COS has some really nice options in the not-crazy price category.)

A straw bag. I think the coolest holiday bags I’ve seen have all been random old straw or raffia bags from unidentifiable brands. My daughter has a small one she picked up from Dille et Kamille, and it looks great. The main benefit of these kinds of bags, apart from looking nonchalant, is that they go with almost everything. And they are cheap. I am of course immediately going to undercut myself by saying that I ordered an expensive straw bag from Loewe (if you want to go designer, I think Loewe does the best ones). Then again, it looks like it will not arrive on time for me to take it to Greece, so I may still end up buying a local 20-euro version. Just a word of clarification: I am not talking of true basket bags here. Although they have a similar vibe and work well in summer, basket bags that are actually shaped like baskets are difficult to pack.

Black bikini, white swimsuit. Swimwear is the part of my holiday wardrobe that I struggle with the most. Somehow now matter what style I wear, I end up looking much worse than I do naked. But, well, something has to be worn. Leaving aside the cut, as it’s extremely individual, my view is that black and white are the most stylish options. I am going with a black bikini (I have a Marysia set that is a few years old) and a white one-piece (from Arket, just bought), but you do it the other way around and look equally great. If you are serious about maximising a small travel wardrobe, look for something that works as a top as well – the Arket swimsuit absolutely does.

Tan sandals. My position on this topic has not changed for at least 15 years: a good pair of tan/brown leather sandals is the single best option for holidays. I do like the iconic Hermes sandals that are ubiquitous on Instagram. While they are outrageously expensive, you could easily wear them for ten years without feeling unfashionable. For now, I am happy with my Dune sandals (you can see me wearing them in that old post) that are going to be a decade old soon: I haven’t found anything I like significantly more and I’m perfectly content to continue wearing them. I love that they are secure around the foot, but there is nothing between my toes – I cannot stand the feeling. Otherwise I probably would have ordered these Soeur sandals, as I really like how they look. Sezane has some nice pairs as well, as do Ancient Greek Sandals (you just have to wade through the myriad of options).

Birkenstocks. I know this is very specific, but hear me out. While I adore stylish leather sandals, most of them are not designed for longer walks – they don’t support the foot at all. Birkenstocks do. I’m sure there are also other brands that do similar styles, but 1) Birkenstock is the original and 2) the brand is currently also very fashionable. I am very grateful for the latter, as I fully admit I would not have checked them out otherwise. I don’t think there is a better combination of comfort, hot-weather-appropriateness and trend-consciousness out there at the moment, so carpe diem! I own these. (If your hot weather holiday is in a city, I would replace Birkenstocks with lightweight trainers, something with mesh like New Balance 530s – I find a closed shoe works better in a big city.)

Large sunglasses. This is likely to be controversial, but I say that if you need to choose one area where to spend, I would spend here. It’s not because I think designer sunglasses are so much better than non-designer ones – my current favourite pair is from & Other Stories. It’s because if the rest of your summer wardrobe is rather casual, luxury sunglasses will add a bit of polish and ‘elevate’ the look, as influencers are fond of saying. It’s also the easiest way to add a bit of a fashion edge to classic clothes – something from Bottega, for example? But if the budget doesn’t stretch to that, I think sporty, futuristic sunglasses can have the same effect for the fraction of the price. For Estonians (and why not others), SU.VI does a wide selection of great mid-priced sunglasses. I love my yellow pair.

A scarf. This is not an essential and I’m in general a bit skeptical of these gimmicky ‘you can wear it in 400 ways!’ things. But a silk scarf takes very little space in your suitcase and if well chosen, can be helpful. You can use it to cover your hair, wear as a simple top and tie to your bag. The latter trick is particularly useful when you only have one bag and you want to add a colour to it that it originally doesn’t have, to make it work better with your outfit.

I’m afraid this is horrifically long and also too late for most people, as we are already in the second half of August. But if the main thesis of this post holds, it should be exactly as relevant next summer…