Because your suitcase deserves better than a repeat of last year’s rotation.
Whether you’re heading to a whitewashed Mykonos terrace, a Côte d’Azur dinner that starts at nine and ends at never, or just a long weekend somewhere the sun actually shows up, the right dress does most of the work. Good holiday dressing is deceptively specific: you need something that survives a full day of cobblestones and still looks intentional by evening, or something so quietly elegant that the resort pool and the dinner table feel equally at home in it. The two are rarely the same dress, which is why packing is genuinely hard.
The good news: this summer’s options are very good. We’ve been through the rails, the wish lists, the URLs our friends sent us at midnight, and the designer concessions we are not remotely embarrassed about. What follows is our actual shortlist, broken down by occasion, with our honest opinions on all of it.
How we chose: We looked for dresses that could handle real holiday conditions (heat, cobblestones, a long lunch that goes into evening) without losing their shape or their point. We prioritised interesting fabrics, clean construction, and cuts that actually flatter, and we verified details, availability, and pricing before including anything.
Naked Cashmere Gillian Floral Silk Chiffon Midi Dress, Naked Cashmere
Best for: Slow mornings and sundowner terraces
Price: £304. Available in Matcha and Ecru.
There is something almost impossibly pretty about this one. A fluid midi in double-layer silk chiffon, it has a classic crew neck, shell buttons, a delicate keyhole at the back, and an allover floral vine motif that manages to feel grown-up rather than girlish. The semi-sheer quality means it moves beautifully in heat without clinging, and the double layer stops it feeling too risky. Naked Cashmere’s thing is refined simplicity done in exceptional fabrics, and the Gillian is a good example of why that formula works. The Matcha colourway, in particular, is exactly the kind of green that looks good on almost everyone. Pack it, don’t overthink it.
Maya Striped Cotton Dress, Ashaki
Best for: City days and long gallery afternoons
Price: $1,300
Yes, it’s a significant investment. Ashaki is a DTC brand with a very specific point of view: considered, artisan-quality pieces made to last, which means the price reflects construction rather than a logo. The Maya is a striped cotton midi with a sculptural quality that reads as genuinely architectural on the body. It’s the kind of dress that works in a city you want to take seriously, where you’re walking a lot, eating lunch at somewhere without menus on the wall, and need to look like you thought about getting dressed without looking like you tried. If you’re the person who rotates the same three pieces for ten years, this is for you.
Daisy Linen Dress, Schöffel Country
Best for: Village fêtes, coastal lunches, anywhere with gravel
Price: £135
Schöffel is better known for country outerwear than summer dresses, but the Daisy is a quiet hit for a reason. It’s 100% linen in a warm oat, charming without being precious, and the kind of thing that looks better slightly rumpled. Very much a “packed in a weekend bag and arrived looking fine” dress. Not the most directional thing on this list, but if you want something breathable, easy, and genuinely wearable for a long afternoon outside, it earns its place. Good news for those of us who iron reluctantly: linen’s whole personality is that it creases.
Jeany Silk Maxi Dress, Reformation
Best for: Evening, full stop
Price: $348 (also available via Farfetch in GBP)
The Jeany has become one of those quietly ubiquitous dresses that you spot in approximately every aspirational holiday photograph, and it’s earned it. Full-length, fitted, 100% silk charmeuse, halterneck with adjustable ties and an open back with buttons. It skims rather than clings. It catches the light without screaming for attention. In the Fior di Latte (a creamy white) or the Guava (a warm coral), it reads as properly dressed without requiring any accessories to justify itself. A word of warning: it runs slightly large, and the length is designed to graze the floor with heels, so factor that in before you check out.
Tania Maxi Dress, ba&sh
Best for: Effortless evening dressing without effort
Price: £325
ba&sh do a specific kind of French-girl elegant that never quite tips over into costume, and the Tania is a clean example of it. A relaxed maxi in vanilla, with a V-neck, a subtle waist cut-out framed by a small metal jewel detail, and a side zip for clean lines. The fabrication is a smooth recycled synthetic that moves well and photographs beautifully. It’s not the most complicated dress on this list, which is entirely the point. Throw it on, add sandals, done. The kind of piece that makes it look like you barely thought about it, which as we all know takes considerable effort.
Cotton-Blend Lace-Trim Flippy Dress, Reiss
Best for: The classic white dress slot
Price: £225 (approx)
Reiss makes very good versions of things that don’t need to be overthought, and this is one of them. A white cotton-blend flippy dress with delicate lace trim that elevates it just enough without tipping into bridal territory. The silhouette is relaxed and easy, which means it works equally well with flat sandals and a beach bag as it does with kitten heels for dinner. The kind of holiday dress that earns its suitcase space every single trip. Come on, everyone needs at least one white dress.
Tara Linen Tie-Waist Tailored Midi Dress, Reiss
Best for: City days that turn into dinner
Price: £255 (approx)
The Tara is proper grown-up linen dressing. It’s 100% linen in neutral, with peak lapels on the sleeveless bodice, pleat detailing, side slip pockets, a self-tie waist belt, and an open back with non-slip taping. It wears like tailoring that forgot to be serious, which is quite a specific trick to pull off. Good for a city you’re treating as a proper destination rather than a backdrop, the kind of place where you want to look considered and mobile simultaneously. The peak lapels are the detail that makes it; they stop it reading as a simple sundress and give it an actual point of view.
Solstice Logo-Jacquard Fringed Cotton-Terry Mini Dress, Zimmermann
Best for: Pool to lunch, resort without trying
Price: £395
Zimmermann does resort dressing better than almost anyone, and the Solstice is one of their best this summer. Cotton-terry jacquard-woven with a logo pattern, fringed hem, elasticated neckline, adjustable straps (removable completely, if you like). It’s essentially the luxury version of throwing something over your swimsuit that actually looks like you planned to be wearing it. Absorbent, lightweight, and the fringe moves well. The kind of piece that photographs like it cost twice as much. Don’t miss this one if you’re travelling anywhere with a pool worth dressing for.
Leontina Dress, Rat & Boa
Best for: Evening out, thigh-grazing confidence
Price: £195
Rat & Boa have built a devoted following on the back of exactly this kind of piece: a body-skimming animal-print mini wrap dress with real construction behind it. The Leontina has buttons on the centre front, a self-tie on the skirt side, and enough structure to look deliberate rather than thrown on. It’s thigh-grazing and not remotely apologetic about it, which is exactly what a holiday evening dress should be. Non-sheer, which matters more than you’d think when the lighting is unflattering. An instant classic in the brand’s world, and at £195 against everything else on this list, an easy yes.
Gathered Organic Cotton-Poplin Halterneck Maxi Dress, Matteau
Best for: Slow travel, the kind of trip you’d call a retreat
Price: £405
Sydney-based Matteau makes resort dressing for people who find most resort dressing fussy. Minimal, considered, and made from certified organic cotton-poplin, the gathered halterneck maxi has long lace-up ties at the back that can be adjusted to create either a strapless or halter neckline. A gathered bodice, a floaty skirt, hidden pockets. The NET SUSTAIN label means it’s made to a specific environmental standard, which matters to a growing number of us. It’s not the loudest dress you’ll pack, but in neutrals it has a calm, effortless quality that’s genuinely hard to replicate at this price point.
Silk A-Line Mini Dress, Camilla at Harrods
Best for: The resort hotel dinner you want to dress up for
Price: £770 (approx $985 USD)
Camilla Franks’ label is the ultimate resort splurge, and if you’re going to do it, the silk A-line mini is the one. 100% silk with a relaxed fit that falls to a fringed hemline and sleeves, in a Turkish-inspired print of florals and tiled motifs that is precisely as maximalist as it sounds and looks considerably better in person. The print work on Camilla pieces is extraordinary, and the silk quality is genuinely noticeable. For those of us who save the statement dress for the one really good dinner on a trip, this is that dress. It photographs like a painting, which, when you think about the prints, is almost literally what it is.
Cotton-Blend Asymmetric Dress, The White Company
Best for: City days, understated elegance
Available in Dusty Clay
The White Company’s asymmetric dress is the quiet one on the list, and sometimes that’s exactly what you need. A cotton-blend construction in the warmest dusty clay (a muted terracotta-adjacent tone that works with virtually everything), with a tiered asymmetric hem for movement and drape. It’s the dress for the city day where you want to look like you got dressed with intention but didn’t spend an hour at it. Clean, breathable, and the kind of thing that packs without drama and comes out looking fine. Pairs with almost every sandal you own, which we consider a virtue.
