What to Wear in Santorini – Silk Maxi Dresses

Santorini has a way of making everything feel more beautiful — the light, the landscape, the pace of life. What you wear should match that feeling. Whether you are wandering the clifftop villages, lunching at a beach club, or watching the sun sink into the caldera, the right dress makes every moment feel effortless.

"When packing for a holiday, I start with the key pieces I love, my Monterey orange silk kaftan, my white cotton Paloma beach dress. Not forgetting my go to holiday dress that has travelled, and in so many photographs my silk yellow Santorini dress. I then lay out each kaftan and dress on the bed and build my accessories around them. Daytime chunky sandals that are comfortable and have a leather upper are a must. Delicate metallic sandals that I can pop into my beach bag if I go straight from the beach to dinner." Lindsey Brown, designer and founder.

What to Wear Sightseeing in Santorini

Exploring Oia's winding lanes and Fira's clifftop paths calls for something that moves as beautifully as the scenery. For daytime sightseeing, our white cotton beach dresses are a joy to wear in the Aegean heat. The Toulouse is a lovely choice if you prefer a shorter length, while the Paloma, our best-selling cotton beach dress, with a short dropped sleeve and flattering v neckline, offers a more covered silhouette that protects your arms and shoulders from the sun. Available in three colours and sizes XS–3XL, it is true to size and flattering across all figures. White is so cool to wear as it reflects the heat and combined with the soft cotton crinkle fabric, a beach dress that is breathable is a must. The hand beaded accents of this seasons new colourway of cobalt blue are simply stunning. When you discover the Lindsey Brown cotton beach dress that suits you, it will transform how you feel on holiday, as dressing comfortably and liking your outfit can lift your whole mood.

Our pick of beach dresses for sightseeing and beach days

  • White short sleeveless cotton beach dress named Toulouse XS–3XL
  • White and blue elasticated cotton beach dress named Paloma XS–2XL
white floaty cotton beach dresses to wear in Santorini by Lindsey Brown resort wear

What to Wear to Beach Clubs

Santorini's beach clubs — from Ammoudi Bay to Perivolos — have a glamour all of their own. Our Santorini silk maxi dress is ideal for beach clubs and sunset dinners, with a fluid silhouette that feels glamorous yet effortless in the island heat. In yellow or turquoise, it looks particularly striking against the deep blue of the caldera. We often think of blue when dressing for Greece, but we love the idea of contrasting against the landscape with something unexpected. Yellow brings warmth and vibrancy against Santorini's whitewashed backdrop and dark volcanic landscape.

Our pick of silk kaftans for beach clubs

  • Yellow silk bloused hand tie dye silk kaftan named Monterey S-M and L-XL
  • Blue and pink printed halterneck silk crepe dress named MonteCarlo OneSize
silk kaftans to wear on holiday by Lindsey Brown resort wear

What to Wear for Sunset Dinners

There is no sunset quite like Santorini's — and your dress should rise to the occasion. Our Santorini silk maxi dress in yellow or turquoise was made for evenings like this: candlelit terraces, cliffside restaurants, the last of the light catching the fluid drape of silk. Pair with heeled sandals and simple gold jewellery and let the dress do the rest.

The Original Santorini dress

  • Yellow silk ombre maxi dress named Santorini XS–2XL
  • Turquoise silk ombre maxi dress named Santorini XS–2XL

What to Pack for Santorini

The art of packing for Santorini is versatility without bulk. Silk is ideal for travel — lightweight, easy to hand wash and quick to steam if needed. Our silk resort dresses move from beach to dinner with just a change of shoes and accessories, so two or three pieces can carry you through a full week with ease. One silk Santorini dress, a midi cotton beach dress like Melbourne, a silk kaftan dress like Monterey and a shorter cotton dress Paloma for daytime trips and beach days. Pack embellished and silk styles inside a pillowcase inside your suitcase to protect embellishments and keep them looking beautiful for future holidays. Another top tip, travel with a hand held steamer, so much easier than a travel iron and your dresses will be pressed in no time.

silk floaty maxi dresses to wear on holiday in Santorini by Lindsey Brown resort wear

Explore our full luxury resort wear for the Greek Islands collection for more inspiration, or read our guide on what to wear to a wedding in Greece for inspiration on dressing for the most special of occasions.