• Natalia Anakkar

How to get effortless Santorini style: what to wear

Updated: Mar 31, 2018

I can't believe it was almost this time last year that I went to the stunning Grecian island of Santorini!


When I packed my suitcase for this trip, I knew I would need a variety of outfits, some casual for the day and some dressy for the night.


Daytime checklist:

  • Bikini

  • Strappy top

  • Denim shorts

  • Thin cardigan (for those breezy moments)

  • Sunnies

  • flip flops

  • Walking shoes (converse, sketchers, trainers)

  • Wedges (for dressier day time occasions/ you want to look model ready on the beach)

  • Jeans (not essential)

  • Beach bag/bum bag/over the shoulder small bag (depends on activity)


First things first, bikinis!

I ordered two new bikinis for this holiday, one black with white straps and the other bright coral with blue and white stripes to really blend in with those fantastic surroundings I knew Santorini was blessed with. Colour is a must and I always find that coral is the perfect choice for complementing a tan. Try a black and white wrap around bikini or bright orange plunge bikini similar to the ones I wore, they would work perfectly in Santorini or any Greek island for that matter. Take your pick!




For the day I knew it would be hot for the time of year so I packed a few different items. One of my favourite pieces were my Levi denim jean shorts that my boyfriend bought me back from Las Vegas. They were super cute especially with the cherry logo stitched on that made me love them even more. I threw these on at every chance I got because they were so comfy and I loved having my legs out feeling free in the fresh air. Pair these with a strappy top and flipflops and you're good to go. I would recommend at least a few strappy tops in nude, bright colours and white (which is always a winner and goes with anything). Then you've got your summer dresses which are a must for something other than the American Girl get up all about the denim. Dresses in Santorini are great because they don't restrict you in anyway which is what you want in that hot weather. You want to be comfortable but still look good! Floaty dresses are a great choice for this and it's the best feeling to prance around the island feeling girlie. Plus, you can always wear your bikini underneath for those sunbathing quickies! If you're at all like me then you'll be in your bikini any chance you get. Talk about sun addict! You stumble upon lots of little coves and deserted islands in Santorini so you don't want to be caught out the one time you don't have your costume. I mean, there's always skinny dipping but hey, you didn't hear that from me.


Shoes, ah yes shoes, well where do you start with that. Actually it's pretty darn easy. You NEED flipflops, obviously! I wore Ted Baker flipflops that were bright pink and have been very good to me, they don't wear too quickly due to being plastic rather than rubber. If you had nothing but a pair of these bad boys you'd be just fine but you would be restricted with the activities you choose to do. If you want to explore the island and make the most of it, be prepared for walking, a lot of walking. Flip flops aren't ideal for this purpose unless it's just beach you're covering of course. Trust me, I've been there and it isn't fun, the blisters cause so many problems and a lot of moaning - which your partner is never going to thank you for! Take walking style shoes like a pair of converse or sketchers. My trusty sketchers have got me to the top of many a mountain in my time. Trainers are always a winner but maybe you want to have these aside for any other exercise you may do other than walking maybe you're keen and want to do an early morning sprint up and down the endless steps that Santorini has plenty of. You'll definitely feel the burn with the inclines there. If not, go for it with the trainers, either way it's a personal preference. Even if they aren't the sexiest you'll be thankful later on when you can slip on those killer heels for dinner reservations and not want to kill yourself from the pain. It's not worth it. The days are for adventures and lounging around on the beach so save the dressy outfits and enjoy being cool and casual in the sun. Wedges are your best friend on holiday here. Comfier than heels and still maintaining that beach vibe. I bought a pair of silver strappy wedges that worked so well with dresses, jeans, you name it. I love all styles of wedges especially gorgeous sparkly ones, stylish embellished ones, pretty jewelled ones and I'm so into cross over wedges because they keep your feet in, so snug and comfy. Don't forget to check out lower heeled wedges for those of you who prefer less height or feel more comfortable in this style.


Jeans aren't essential in summer as it really doesn't get that cold. In saying this, one or two pairs is acceptable in my book because they do look awesome with wedges and summery tops, and can be dressed up or down. It depends on your individual look and how much space you have in that suitcase, but I love white skinny jeans on holiday, as they are totally summer ready and cream skinny jeans are a little different so make a nice change.


Here are some of my day time outfits from the holiday, what do you think?






















Night time checklist

  • Maxi dress

  • Cute matching two piece

  • Dressy summer dress

  • Sunnies (before sunset/catching those last rays)

  • Killer heels/wedges (outfit preference)

  • Flip flops (if you need to walk back, let's be sensible now)

  • Light cardigan/jacket (depending on the weather)

  • Scarf (perfect finish to any outfit and adds a burst of colour to darker ensembles)

  • Clutch


Time to get dressy and enjoy those sunset evenings with a cocktail in hand. I loved getting dolled up for the night time sessions in Santorini. Whether you are off for a romantic dinner or a few cocktails, everyone loves dressing up here probably because the setting is so gorgeous, it just feels right. I wore my sparkly wedges a lot at night time because we usually walked to the restaurants as they were pretty close to where we were staying which was very convenient. When we got a taxi to Oia or a bit further away I put on my killer heels but took flip flops as a back up. One of my favourite dresses was a black slinky maxi which was a cross over, backless one and I completed this with some black suede point heels. I wore quite a few brightly coloured summer dresses and a two piece crop top and skirt which I absolutely loved.


You can see my night time styles from the holiday at the bottom. What's your favourite?


Accessories are the finishing touch to any outfit so have a few pairs of earrings, some studs and some dangling ones along with a mixture of choker necklaces, dainty pieces and bangles or your fave bracelet. Maybe a statement ring or hair accessory to vary it up. Don't over do it with the accessories, still be you, but extra glam. Take your favourite silk scarf for a pop of colour. This can be used as a classy cover up for when you feel the sea breeze but don't want to put on your jacket and hide your gorgeous dress. Who says you can't be warm yet still a lady of elegance. Take a couple of clutch bags to compliment those outfits. I took a sparkly jewelled clutch with a silver chain and a hand held coloured one to spice up those neutral tones in an outfit. Maybe your flip flops can fit in a slightly bigger clutch or fold up, which would be even more convenient.


Santorini really is a gorgeous, bright and breathtaking part of Greece. Enjoy wearing a range of outfits and making the most of the views and cocktail bars it has to offer. There's a place for every outfit and you'll need a few just for the endless photo opportunities you won't want to miss. Think classy, stylish and 20's beach babe and you'll fit right in!














Catch my "13 amazing must do's for Santorini Virgins" blog soon to see what I got up to on holiday.


Love N x


#Santorini #holiday #fashion #greece #style #fashionblog #summer #styleinspiration #whatiwore #lovethislook #outfits

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