Sugarplum Style | What I Packed & Wore in Greece

Happy holiday week, lovebugs!! We’re headed to the lake this afternoon to celebrate the Fourth and our son’s birthday! What do you have planned?

I’ll be recapping our entire Greece trip, including all the stops, hotels, restaurants, ferries and more…but today is all about what I packed and wore. And hopefully it provides a little outfit inspiration for your long weekend!

Our trip had a lot of moving parts and close connections, so we opted to travel entirely by carry-on! It definitely took more planning on the front-end, and I was ruthless in my choices, but it paid off in the ease and convenience of being able to move from place to place quickly and easily.

I packed according to a color palette, so most everything mixed-and-matched, and each piece could be worn 2-3 times. The weather was warm, so I stuck with mostly cotton tanks and gauzy separates, and had plenty of combinations for the two weeks.

Each outfit is linked under the pic, with sizing included, and you’ll see how I repeated the pieces.

What I Packed for Two Weeks in Greece

  • 1 Skirt
  • 1 Pant
  • 3 Shorts
  • 1 White Tee
  • 6 Tanks
  • 1 Dressier Top
  • 2 Tank Dresses
  • 1 Wrap Dress
  • 1 Jean Jacket
  • 2 Swim Coverups
  • 4 Swimsuits
  • 1 Pajama
  • 7 Undies (we washed in the sink mid-trip)
  • 2 Sandals & 1 Flip Flop
  • 1 Hat
  • 1 Beach/Pool Tote
  • 1 Crossbody Bag

Embroidered Racerback Tank (XS) | Shorts (XS) | Hat (A-Khaki) | Bangles | Sunglasses

Racerback Dress (XS) | Crossbody Bag | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Swimsuit (S) | Hat (A-Khaki) | Bangles | Sunglasses

One Shoulder Ruffle Top (XS) | Tiered Skirt (XS) | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Henley Tank Top (XS) | Wide Leg Pants (XS)| Bangles | Sunglasses

Swimsuit (S) | Hat (A-Khaki) | Bangles | Sunglasses

Dress (S Navy)| Crossbody Bag | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Henley Tank Top (XS) | Shorts (XS) | Hat (A-Khaki) | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses | Roller Bag | Weekender Bag

Tank (XS) | Shorts (XS) | Hat (A-Khaki) | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Swimsuit (S) | Hat (A-Khaki) | Bangles | Sunglasses

Henley Tank Top (XS) | Skirt (S) | Hat (A-Khaki) | Bangles | Sunglasses | Sandals (use code HISUGARPLUM for 20% off!)

Swimsuit (S) |Beach Kimono | Bag | Hat (A-Khaki) | Bangles | Sunglasses

Embroidered Racerback Tank (XS) | Shorts (XS) | Hat | Bangles | Sunglasses

Henley Tank Top (XS) | Shorts (2) | Crossbody Bag | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Swimsuit Top (S) | Bikini Bottom (S) | Beach Kimono | Bag | Hat (A-Khaki) | Bangles | Sunglasses | Sandals (use code HISUGARPLUM for 20% off!)

Swimsuit (S) | Hat (A-Khaki) | Bangles | Sunglasses

Racerback Tank (XS) | Shorts (25) | Flip Flops | Bag | Hat | Bangles | Sunglasses

Cover Up Dress | Bag | Hat | Bangles | Sunglasses

One Shoulder Ruffle Top (XS) | Shorts (25) | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

Racerback Top (XS) | Shorts (25) | Flip FlopsBag | Hat | Bangles | Sunglasses

Dress (XS on sale!) | Hat | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses | Roller Bag | Weekender Bag

Ruffled Tank (XS) | Shorts (XS) | Bag | Hat

Woven Bag (packs completely flat, but holds a ton)

Henley Tank Top (XS) | Shorts (2) | Crossbody Bag | Sandals (use code HISUGARPLUM for 20% off!) | Bangles | Sunglasses

As for my travel outfit (it’s a long travel day from Dallas!), I chose these wide leg pants, which are pajama soft, but look fairly chic and hold their shape well. At the last minute, I added my beloved Miller sandals, but honestly never wore them once in Greece.

The cobbled, dusty streets just were’t a good match for them, and I lived in these strappy sandals. I can’t say enough about them for travel and everyday, plus they’re 20% off with code HISUGARPLUM).

I also never travel without this jean jacket and a white tee.

Wide Leg Pant (XS) | Pocket Tee | Jean Jacket | Sandal | Roller Bag | Weekender Bag

Obviously I couldn’t have managed all those pieces in a carry-on without my packing cubes! You’ve heard me sing the praises of them for years, and they’re honestly what made the carry-on life possible!

I saved space by leaving my hair dryer behind, so the hat came in handy for multiple reasons. I also limited my accessories to the bangle set. You can find a full tutorial of how I packed everything in my bag, plus a breakdown of what’s in my toiletry bag and carry-on here. And find all my Travel Essentials here.

I hope this post is helpful in packing for your own adventure! Leave any additional questions in the comments, and let me know what details you want to see in the trip recaps! Happy Fourth, lovebugs!


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Leave a Comment


  1. Gina wrote:

    Great post! How did you pack the hat and keep its shape?

    Posted 7.3.19 Reply
  2. Sandy wrote:

    What a great recap of style! Especially for our fleeting summer here in the north.
    I heard that the white paint was toned down on all the lovely buildings on Santorini because the residents were getting cataracts. Whoa.
    Thanks SP, I want!

    Posted 7.3.19 Reply
  3. Jill Dickinson wrote:

    Great job at packing. Just one question, you had so many white pieces and wore them multiple times, how did you keep them clean and white while wearing multiple times on vacation?
    Can’t wait for your vacation details post!

    Posted 7.3.19 Reply
    • Cassie wrote:

      I did have to spot clean my shorts a few times! The linen shorts I washed in the sink once and left them to dry all day on the patio! I wore those a lot more than I’d anticipated, so they needed a little refresh! 😉

      Posted 7.4.19 Reply
  4. Beth K wrote:

    I can’t imagine just taking a carry-on, but wow you nailed it! Hoping the embroidered racerback tank will make it for our 4th festivities this weekend! It’s the perfect top for celebrating!

    Posted 7.3.19 Reply
  5. Mary wrote:

    Hello from Athens Greece , I am big fan to your blog . What news you are here , I want to meet you but I am in athens now. . Santorini is magical, beautiful , happy summer holidays.

    Posted 7.3.19 Reply
  6. patti wrote:

    Hi! Can you tell us about the weekender bag – did it fit nicely under the seat? And more importantly – how much of everything can you stuff it with lol? Thank you!

    Posted 7.3.19 Reply
    • Cassie wrote:

      Yes, it fits under the seat (well, depending on how much you stuffed it with, I guess!) and in the overhead. I shared everything I packed in mine in that Instagram Story linked at the bottom of the post! xo

      Posted 7.4.19 Reply
  7. Lynn wrote:

    Got the bags. Can’t wait to pack for next trip! My dog ended up better than expected so I splurged for my fave piece- the Naxos top. Real interaction on walking into my daughters house wearing them…daughter:”wait, you ordered that? Looks great! I just ordered it in the blue!” Too funny! We dress similarly but have never purchased the same item- quite a compliment!

    Posted 7.3.19 Reply
    • Cassie wrote:

      I love that!! So happy you love the top!

      Posted 7.4.19 Reply
  8. Kathleen Dean wrote:

    Thanks for taking us along on your amazing trip! In your recap I’d love to see some comments about the planning process – how do you decide what you want to see/do, where to stay, etc. How do you determine an itinerary and the day to day.

    Posted 7.3.19 Reply
  9. Patricia wrote:

    I Just returned from a month in Europe, including a week on land in Greece (Crete) and a week bareboat sailing in the Greek islands followed by 2 weeks in the South of France. Like you, I did the entire month with 1 carry-on and a personal tote. Greece is a hot and dry climate. Things dry quickly. I brought along 2 swimsuits, but honestly could have lived with only one and we swam everyday. Beaches in Greece and France are rocky. I was very glad I had room for my water shoes which doubled as trainers for some light hiking. I adore the embroidered tank you brought with you and everyone was in wide legged, light weight pants.

    Posted 7.3.19 Reply
    • Cassie wrote:

      That sounds like a dream trip….I’m coming with you next time!!

      Posted 7.4.19 Reply
  10. Sevahn wrote:

    You belong on the cover of Conde Nast Traveler magazine! Happy 4th!!

    Posted 7.3.19 Reply
  11. Christyn wrote:

    Thanks for sharing!!! You’ve inspired my plans for a 20th anniversary surprise trip next year for my husband and I- GREECE! I went when in my 20’s, but now it’s time for a REAL adventure! I’ll surely be back to use your plans to inspire my own! Just received my order form the summer of color collection- and the pieces I selected work perfectly for my taller frame! Super excited to wear them!

    Posted 7.3.19 Reply
    • Cassie wrote:

      I’m so excited to hear that!!!

      Posted 7.4.19 Reply
  12. Corinne wrote:

    Hey Cassie
    How do you manage your limited clothes to stay fresh. After a long (or short) travelday my clothes are always grosse (in my opinion). And I sweat a lot so I‘m more than happy to enjoy every day a new top. If I stay for a couple of days I could wash my clothes in the sink, but with a round trip not. When will my clothes dry? And second, I‘m on holiday I don‘t want to work 😉

    Greetings Corinne

    Posted 7.4.19 Reply
    • Cassie wrote:

      Hi Corinne! I layer dryer sheets between my clothes to keep them smelling fresh throughout the trip! But yes, I will wash a few things in the sink, or use the hotel laundry service. Especially for my travel outfit…if I only pack one for the roundtrip, I’ll launder it before heading home.

      Posted 7.4.19 Reply
      • patti wrote:

        interesting! can you include tips like this in your next recap as well? I absolutely want to burn my travel clothes after wearing them for what always ends up being a long day and I somehow never have used the hotel laundry service (how silly!).

        Posted 7.7.19 Reply
  13. Shelly wrote:

    Cassie, Thanks so much for sharing this! It seemed impossible that one could get everything in a carry on for such a big trip. This makes sense to me now. Smart packing.

    Posted 7.5.19 Reply
  14. Maureen wrote:

    I agree that the walking in Greece wasn’t ideal for sandals but neither it was in Portugal as well when my family went! You packed so many cute outfits. They all look so cute, comfy and perfect for the summer heat! I need to look into packing cubes. They sound magical!


    Posted 7.7.19 Reply
  15. Dionne wrote:

    I love your carry on but the Nordstrom description says the bag must be checked so just wondering if you were able to store it overhead on your flights.

    Posted 7.11.19 Reply
    • Coleen wrote:

      Wondering this too! We reading through the comments looking for the answer to this question.

      Posted 7.12.19 Reply
  16. Lisa wrote:

    Love this one, too! You are so creative with mixing and matching. I just scored that color block suit – so cute and out of my comfort zone, but you totally inspired me to try something new.

    Posted 7.24.19 Reply
  17. Lexie wrote:

    In Australia your tan bag is considered all you can carry on and your case would be a checked bag. Just for you guys that might be allowed back to Australia one day post covid.

    Posted 8.26.20 Reply