I'm a Stylist—Here's Everything I Just Wore on Holiday in Santorini

This year has been a particularly good year for travel. I headed to the Philippines to relive my “travelling around South East Asia” era at the start of the year, I watched my first tennis match in Barcelona and one of my most recent trips was a first visit to Santorini. Staying at the newly-opened Santo Mine resort, the breathtaking views, Instagrammable sunsets, bread with every meal and a taste of the Greek wines is what sold the island to me. What I love most about being away is the the lack of decision making, and although choosing an outfit to wear to dinner or for a day of exploring the beautiful Oia (it was only a 7-minute walk from the hotel) is a decision to make, I also get so much joy out of outfit planning.

Like Mykonos, I knew Santorini can be breezy, so I packed oversized shirts and linen trousers for layering along with a light jacket to wear between the plane and the al fresco dinner settings. I’m also all about packing basics I can wear on repeat so vest tops, stretch-waist shorts and interchangeable bikinis were all on my to-pack list. Add to this a few co-ords, some staple accessories (I can never go on holiday without my Loewe basket bag) and I would say these are some of the 7 easiest holiday looks I’ve ever created. And the best part is, you most likely already have them all in your warm-weather wardrobe.

1. Brown Top + Brown Maxi Skirt + Leopard Heels

Style Notes: I’ll take any opportunity to get dressed up, so of course dinner at Santo Mine’s al fresco dinner spot overlooking the sea meant a “nice top” with a maxi skirt and a hint of leopard print through accessories. I’ve got a thing for brown at the moment, so top-to-toe chocolate was one of my first evening looks. With Santorini sometimes being windy, my hair up was a tactical choice!

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2. Orange Dress + Sunglasses + Gold Earrings

Style Notes: Another colour I’m loving this season, is orange. And although it works well with neutrals, I think it’s one of those shades best worn as a monochromatic look—so a matching bag or shoes is always a good idea. I loved the cutout detail on this one-shoulder Asos dress (it’s now sold out, sorry) but I wish it was either a maxi or a mini. Which is why I’ve found a similar mini version from Reformation, below.

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3. Bandeau Top + Striped Trousers

(Image credit: @harriet.davey)

Style Notes: One of those pinch me moments, I was lucky enough to have a private pool overlooking Santorini. And yes, this is when I fell in love with the island—along with my bedroom door that made for the perfect outfit picture spot, of course. I’ve worn my linen-blend striped trousers on heavy rotation this season, and it’s not surprising when they go with everything from a bandeau top to a vest top or oversized shirt. Easily one of my best summer buys.

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4. Skirt Co-ord + Heeled Thong Sandals

(Image credit: @harriet.davey)

Style Notes: I had heard how magical sunsets are in Santorini, but I had to see it to believe it. And yes, the rumours are in fact true. I currently own around ten printed co-ords (they’re so easy to wear no matter the occasion) and I loved this satin style with heels for an easy throw-on-and-go evening outfit. I would also break it up and wear the top with denim shorts and the skirt with a white vest.

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5. Vest Top + Jorts + Ballet Flats

(Image credit: @harriet.dvaey)

Style Notes: I was late to both the jorts and mesh ballet flats parties, but I’m so glad I joined. After a couple of days in Santorini, I soon realised my Chanel dad sandals were not going to be the best option for climbing the cliff-top shops and restaurants in Oia. Top tip: After a few near-slip situations, trainers, chunky sole sandals and some secure ballet flats are perfect for exploring.