Date: Posted on Category: Outfit, Travel Location: ,

Most Instagrammable Spots In Santorini //

If you’ve been on my Instagram, you probably saw that I took a recent trip to Greece – and it was beautiful beyond my expectations. I’ll be sharing all of my outfits along with some of the most Instagrammable spots in Santorini and Mykonos.

I’ve visited many different places at this point, but I don’t think I’ve ever experienced such incredible views, delectable meals, or vivid sunsets. From the crisp white buildings to where the fresh blue sea meets the clear bright skies, every angle was breathtaking. I wanted to do an outfit round up of my favorite looks from Greece to inspire you to dress for the location wherever you’re headed. And if you’re just craving that Mediterranean sun, these looks will satiate that wanderlust in you.

Plaid and Sneakers

I knew this blue plaid wrap dress had to come with me to Greece because the color was so reminiscent of the beautiful roofs in Santorini. And there’s nothing wrong with being a little matchy when you’re going up against something as charming as these windows and doors.

I loved how this outfit melded me right into the environment. Because some of the most Instagrammable spots in Santorini are as simple as their iconic blue doors and pink bougainvilleas!

Dress: (similar here) | Bag: (similar here) | Shoes: Senso

Most Instagrammable Spots In Santorini //


Most Instagrammable Spots In Santorini //

Dress: (similar here) | Shoes: Senso

This beautiful tulle dress had me feeling like a Greek goddess! The lace and sheer cutouts are all important details that made me feel magical. How divine does it look grazing up and down those stone steps? A dress like this gives the illusion of an ancient goddess floating along the white walls. I couldn’t have picked a better one to come with me.

Pretty in Peach

Most Instagrammable Spots In Santorini //

Most Instagrammable Spots In Santorini //

Robe: (similar here) | Sneakers: Senso

I wasn’t kidding when I said I dressed for the architecture. I loved the look of the peach structures with the pastel blue trimmings against white walls, so I decided to go along with the color scheme. This peach robe complemented these walls in Santorini beautifully while allowing me to feel most comfortable in my daily strolls.

Most Instagrammable Spots In Santorini //

Shorts: (similar here) | Top: (similar here) | Shoes: (similar here) | Earrings: (similar here)

Most Instagrammable Spots In Santorini //

Bright Whites

I knew NYC temperatures would probably drop as soon as I got back, so I was sure to indulge in all the sunbathing I could… What better way to do that than in comfy white cutoffs and a low-cut cami? This might just be the last time I can wear shorts for a while… There I go again matching the scenery shamelessly with my blue earrings and straw bag!

Classic Stripes

Dress: (similar here) | Shoes: (similar here)

A pattern you can never go wrong with when you know there will be plenty of sun is stripes! The flowy cut of this dress made it the perfect vacation garment because it really allows the skin to breathe. I also loved the button details and pockets (a must when traveling).

Photo tip: Look out for peach and pink shaded facades. Santorini is known for its whites and blue but some of it’s most instagrammable spots are its other unexpected colors!

Most Instagrammable Spots In Santorini //


Romantic Evenings

Most Instagrammable Spots In Santorini //

Dress: (similar here | Necklace: (similar here)

What can be more luxe and exquisite than velvet? This dress was pure splendid with its low cut neckline, flutter sleeves, and rope details around the waist. This was another one of my greek goddess moments in one of the most Instagrammable spots in Santorini! It was well-suited for a romantic meal like this with a spectacular view! I couldn’t have asked for better light.

Mykonos Flares

Most Instagrammable Spot In Mykonos //

Dress: (similar) | Bag: Chloe | Shoes: Senso

Inspired by the sea blues around me, seafoam is just a color that I knew I wanted to wear through the town of Mykonos. My tip for the easiest and comfortable outfit for exploring is sneakers with a dress that has an interesting hem.

For one of the most Instagrammable spots in Mykonos? Look for the roads behind alleys and take spontaneous corners for empty streets all to yourself!

Sunkissed Orange

Most Instagrammable Spot In Mykonos //

Top: (similar here) | Skirt: (similar here) | Shoes: Senso

I visited Greece at the beginning of October, but it felt like summer goes on all year round in Mykonos. So, I couldn’t help but channel some bright and summery shades of golden orange. This pop of brightness together with the infamous giant bougainvillea bushes makes me so happy.

Rosé Hues

Most Instagrammable Spot In Mykonos //

Most Instagrammable Spot In Mykonos //

Dress: Tome (similar) | Shoes: Senso

Bold red is a color that I’ve always been drawn to. But in Mykonos, anything red truly comes alive. I loved this number on a quiet evening by the seaside.

Photo tip for Mykonos is to look out for their iconic windmills. They will add an epic backdrop to any of your photos!

Most Instagrammable Spot In Mykonos //

See you guys on the next adventure!


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  • nicolette

    I am loving all of these pictures! Greece is amazing I went for our honeymoon and it was magical.

    Love the styles and picks!


    • Awesome! It definitely is a great destination for a honeymoon 🙂

  • Ally Shiny

    these pictures are just amazing, wow!!

    xoxo ally
    [ ]

  • This is serious vacation goals. That velvet dress is like my dream dress! I’ve seeing velvet wrap dresses everywhere in stores and I really want one 🙂
    Nicolette |

  • Briana Trevino

    Beyond perfect! The peach colored outfit is my favorite!


  • Wow so jealous, now I gotta add Greece to my list of places to travel. The outfits and photography in this post is just beautiful so picturesque and like a fantasy! I love how you matched your outfits to go with the scenery!

    • You need to. It’s just beautiful!

  • Simone Bostrøm

    What camera do you use? <3

  • maliblue mymind

    loved this post, the scenes you chose and your outfits! Greek islands have always been on my bucket list


  • I have been admiring these photos on your Insta post after post. The scenery is just so gorgeous and your outfits fit right into it <3

    x Kristjaana

    • Wow thank you so much!! <3

  • OH MY GOD. Your photos are STUNNING. I love that you matched with your surroundings and that tulle outfit was just BREATH TAKING!


  • Your pics are taking me back to my trip to Greece this spring- SO AMAZING! These shots are stunning, babe, and you found all the best places!

    Le Stylo Rouge

    • I did see that post of yours and I remember wanting to go there 🙂

  • Elegant Duchess

    wow your outfits are fantastic, that white tulle dress is breath taking! Greece is so beautiful, i so want to go back there after seeing your photos. xx

  • These view are absolutely gorgeous!!

    Effortlessly Sophisticated

    • Oh yes they truly are 🙂

  • Always so beautiful! x

  • The Gold Lipstick

    Absolutely love it!

    Mireia from TGL

  • Natali

    Oh my, as if Santorini and Mykonos haven’t already looked like a pure paradise, those photos just reminded me of how magical both places are and how much I can’t wait to visit them. 🙂

    • Both are magical indeed. Thanks Natali – hope you can visit them soon. 🙂

  • I have visited Santorini twice and it is so breathtakingly beautiful <3
    Your photos are magical! 🙂

  • All of these photos are magical and I am obsessed with your outfits! We had planned to go to Greece last year, but went to Switzerland instead 🙂 It’s on the bucketlist and luckily, I have family there to stay with!


    • Cool Liz. Hope you get to visit soon. Thanks for stopping by! 🙂

  • Kritsida

    Your outfits are always on point! And I love all these pictures, they are absolutely GORGEOUS!
    x. kritsida

  • Christine

    I’ve always wanted to go to Greece and I can only imagine how beautiful it is there. I love all these looks from the casual robe and sneakers to the stripes and the gorgeous tulle dress. Wow, what an incredible place to showcase all these fabulous looks. Thanks for sharing your adventures and all your wonderful clothes! xoxo, Christine

  • Wow these photos are breathtaking!! I really want to go to Greece, every corner looks so gorgeous. Hopefully I’ll be able to make it soon 🙂

    • You need to add it to your bucket list, Maria. It’s unbelievably beautiful!

  • Ellie

    As always: Just a great post!<3

  • Radi

    So Stunning! I love the way you matched the beauty of the Greek islands. All outfits are jaw dropping!!!
    Happy day Jessica!

  • Jessi Malay

    Looooove love this guide! I can’t wait to vacation over there! Thanks for sharing such wonderful photos!

    XO, Jessi

    • You’re welcome Jessi. I can’t recommend it enough 🙂

  • Carrie @ Curly Crafty Mom

    Gosh, every single one of these photos is just amazingly beautiful in its own way! I would love to go here!


    • Yes Carrie. You definitely should!

  • All these places are seriously so gorgeous! Thank you for sharing with us.

    xx, Maryam

    • You’re welcome Maryam!! xx

  • Absolutely unreal. Love this post!

    • Thank you Angie <3 Appreciate you stopping by!

  • you are just amazing & gorgeous pictures are outstanding …. 🙂 wp best

  • Ophelia Tang

    The spots are def insta-worthy! Your feed and photos are always stunning!

    XOXO //
    SINCERELY OPHELIA | NYC Petite Fashion Blogger

  • AH this looks and sounds like such a magical trip! What a stunning location, beautifully captured.
    Your looks are all perfectly on point!


  • Thank you so much for sharing all of these great places to take photos for Instagram! 🙂 <3 All of your content is so beautiful! I am literally in love with all of your outfits!

    XO, Elizabeth

  • omg it is so incredible there, I want to go

    • I highly recommend it, Laura. 🙂

  • All these places are so amazing ! Thanks for sharing such wonderful photos !


    • You’re welcome, Nina 🙂

  • WOW, Jess, your photos are truly breathtaking!
    Have a wonderful week.

  • I am so excited to visiting these places next year. They’re just stunning x

    Tiffany Tales | Lifestyle & Beauty

    • Excited for you, Tiffany! Enjoy xx

  • These pictures are unreal!!! Did you have a photographer come with you? I love everything and every outfit! Killing it girl!

    Katherine |

  • Jesss, I’ve been stalking your Instagram constantly just to keep up with you on your trip! I love every pic and you look incredible in all of them! Looks like such an incredible trip 🙂 x


    • Wow thanks! It was truly incredible!

  • These are incredible photos! I would love to visit Santorini one day, my sister went and got so many great photos just like you did. It’s a really lovely spot! 🙂

    Hope you are having a lovely week and your weather is better than ours, haha! Cold and rainy here in Brisbane.

    Away From The Blue Blog

    • It was so lovely. Thanks Mica!

  • Omg How it´s possible to select 2 or 3 looks ! No way, you look marvelous on every them!
    Coco and Jeans by Marisa x My Instagram x My Bloglovin

  • Your pictures are absolutely wonderful, like wow. Santorini looks like such a dream and I really cannot wait until I can visit it. It’s so hard to pick a favourite picture but if I had to choose, I think I would pick the very first one! xx
    Coco Bella Blog

    • It is so photogenic babe 🙂

  • I am just in awe of the scenes in the photos! I love all of the outfits, the plaid was my favorite!

    • They are so beautiful indeed. 🙂

  • I do think that Greece is one of the most photographable places, and therefore you fit in perfectly, Jessica!!
    Absolutely gorgeous, and incredibly stunning—both the views and you!

    • It is! Amazed with its beauty 🙂

  • Naty Diaw
  • You killed Santorini, babe! Your outfits were all on point, I can’t even decide which one is my favorite because you look amazing in all of them!

    xo | Cindy Elena

  • wow! All the pictures are just stunning, can’t even pick a fav!

    Bernie, xx
    The Style Fanatic

  • Amy

    Your outfits go perfectly with the beautiful Greek settings!! I love each look more than the last – you look so amazing, Jess!!

    Hope you had the best time!

    xx, Amy

    • Thank you Amy. I did have a great time!

  • Dominique

    These snaps are blowing me away! Could Greece (and you, of course!) be anymore beautiful!? xx

  • Wow girl great shots ! The blue and white checks and the stripes so Greek , beautiful background matching looks ! But the RED is it !!
    Dress The Part

  • I can’t pick a favourite, I LOVED THEM ALL !!

    Michaela |

  • these photos are WOW!!
    Miki x

  • Theoteom Michael

    BRAVO reallu great! I am from greece! These photos gonna be so amazing!
    Thanks for sharing!
    Check too my posts on
    Teo from ATENA!

  • I hope you get to someday. 🙂

  • Julie

    My word, what a beautiful post! Loving the scenery and the outfits!