What I'd wear on summer vacation
Sharing my vacation outfit inspo and how I'd style it this summer.
By far, one of my most asked questions lately is something along the lines of, “What would you wear in Italy/ Europe/ South of France/ etc this summer?!”.. so I thought I’d do a more in-depth post here of what I would shop for and how I’d style my clothes on summer holidays.
First of all, like any trip or season, we gotta make a list. It doesn’t have to be too specific with the brand name or exact item- but simply creating a general list will ensure your shopping is well rounded and help with only getting pieces you actually need. I make mine in my notes app to keep handy as a reminder when I’m shopping Said list below:
While I won’t go through every category, I have gathered some things that caught my eye lately that I would absolutely wear on vacation!

Let’s start with easy dresses, because if you have this category down, you’re set. In my opinion, a few dresses can take you from day to night in most vacation settings.
Just picked up this Paloma Wool semi-sheer dress. Perfect for vacations as a cover up and can definitely dress it up for the evening! Hoping the fit is all good and we end up liking it! Will style it when it comes in.
I am eying a few mini dresses that I would love for summer and vaca. This one from La Ligne is super a super pretty LBD. Another cute LBD with a 90s vibe high neckline. This is a sweet one from BR, I would probably remove the slip. The ultimate mini for me right now, is this polka beauty from Doen. Honorable mini is this cutie romper from COS in my cart- so easy to just throw on!
I’ve been wearing this Eres dress a ton. I shared more affordable versions recently, so let’s recap them here from Shopbop, and here from Ref.
Super into this asymmetrical, drop waist, flowy number I have on the way.
If this Sir dress was still in my size I would have snatched it up.
More dresses here on the vaca edit.
Next up: the button down. Go classic or have some fun with it. My preferred cover up!
I have collected these Sezane button downs (that come with complimentary embroidery for a sweet personal touch) ((side note, I’ve gifted this to my bride friends with their new initials and they obsess over it!))
Here are a few more I’m loving with personalization options: this men’s shirt from J.Crew and this Sessei one!
As always, get yourself some thrifted men’s button downs for good measure (just scored a Brooks Brothers red stripe from Select Vintage)
I think maxi skirts are great because you can also throw them on with a bikini top and make a very chic day time outfit out of it.
Loving drop waist options like this Reformation skirt + this St. Roche skirt I love and own+ this Modern Citizen option. I would style these with a more cropped top!
What’s a vacation without good swim? For so long, swim was my least favorite category to buy for because I struggled with needing an adjustable waist tie on every top in order to fit comfortably with my bust.
Monday Swimwear has the girls in mind with their designs and that’s why I’ve worn their supportive, yet flattering swim for years. Finding swim that doesn’t look grandma-y, but still supportive should be an Olympic sport.
I also love this one from Hunza G (though not the most supportive), and this one from Left on Friday- if you’re opting for a snatched one piece.
I think a cute basket bag/clutch is always fun on vaca. Here’s a summer bag round up with some new options I just added, including this adorable two-tone crochet raffia bag from Etsy.
Comfy shoes. Sneakers, easy sandals, flip flops- that’s all you’ll need. I
F (if is a strong word) you really need a pair of heels (this speaks to mainly for European destinations), I’d opt for a low, low heel.
Been loving these strappy sandals from the Row, but here are some H&M lace ups with similar vibes. I linked a few more shoe options here in the vaca edit.
You’ll catch me in my Havaianas all summer dressed up high or low. If I’m styling up, I will be reaching for these Essen evening sandals (code: GABS15) or my Row red slides.
Speaking of shoes, I have been hoarding these Cayumas velvet mary-janes and they are so fabulous. I love them as a pop of color with neutral outfit and would be so fun for vacation. Cayumas + Flabelus have very cute options.
Statement pieces: have fun with the basket bags, fun jewels, cute sets, a red sandal, and playful sunnies.
I am also very into these men’s cotton/crotchet short-sleeve cardigans to style on vaca: A&F option + J.Crew option + Etsy option. The men’s sizing will give the most effortless, relaxed draping. I’d wear them as cover-ups or over a dress, even with a skirt or shorts.
A hat I love recommending is this actual packable one from Janessa Leone (one of my favorite brands ever).
Basics: I never forgive myself when I don’t bring jeans on vacation. Specifically, my vintage Levis. I love wearing them at night when it’s more chilly with a casual, delicate top like this, this.. or this. Make sure you have your tanks and tees on deck.
For when your cold: I think a piece like this is very chic, and a cardigan is perfect (Gabriella15 for Jenni Kayne)!
Another thing I love to do before a trip: draw some inspo from good ol’ Pinterest. Here is my SS23 board for some more vaca outfit ideas. I have an older posts here on insta that is vaca-list focused, as well.
Here you will find an updated Vaca Edit with all of the products here, and more.
Buon Viaggio + Kalo Taxidi.. in other words have a good trip!