I normally always travel with a carry-on, but with all the recent reports of checked bags being lost and the chaos of summer travel hitting every airport, I've doubled down on my position. I'm not taking any chances! Or at least I told myself that until I tried to pack for an eight-day vacation to Italy. Let me tell you: It was a process of editing everything down to make sure everything fit in my Away carry-on.
You might be thinking there's no way I was able to pack 21 pieces, but I assure you it's the truth. Everything was lightweight and thin for the high temperatures, so it all rolled up without taking up much room at all. And I was able to bring five pairs of shoes because most of the sandals were packed flat. No vacuum-seal bags needed here!
Since getting back (sadly all vacations must come to an end), I think I pretty much nailed the packing situation because only one item went unworn. Not to brag, but that might be a record for me. The schedule was Rome for four days (I recommend staying at the W Hotel while you're there!), Naples for one, and Sorrento for three. If you're thinking of traveling to Italy or packing for a country with similar weather this time of year, here's everything that made the cut in my small but mighty suitcase.
Maxi Dress + Sneakers
This is one of my most cherished Dôen dresses, as it works for dressy and casual occasions (and has generous stretch for when you eat way too much pasta). I happened to wear this to the first dinner reservation in Rome at Trattoria al Moro by the Trevi Fountain but paired it with Converse so I wouldn't trip up on the very uneven cobblestone streets.
My exact dress is out of stock, but this floral one is pretty similar.
Love this roomy cream-colored one from Reformation. (Just be extra careful about any wine or pasta sauce stains!)
A must for days when you know you're going to be on your feet the entire time.
Linen Shorts + White Tank + Flip-Flops
It was definitely hot outside, so a pair of lightweight linen shorts, a muscle tank, and flip-flops were great items to wear in one outfit and versatile enough to wear with other pieces I brought.
I stayed at the W Rome, which is located in the Via Veneto area and just a short walk away from the shops by the Spanish Steps. It was really the perfect location—especially because I knew I would be hitting up some designer stores. After stopping at Prada, I ended up splurging on some Miu Miu ballet flats to bring back with me.
My top is from Buck Mason, but I'm eyeing this Clyque one too.
These black shorts are perfect.
These are comfortable and go with everything. What's not to love?
Boxer Shorts + Short-Sleeve Button-Down
The next day I trekked from the hotel to the cute neighborhood of Trastevere in some striped boxer shorts from Entireworld (R.I.P.), a striped short-sleeve tee, and one of the two bags I brought for the whole trip. This one is from IMAGO-A.
Again, since many of the clothes I brought were super thin to prepare for temperatures in the high 80s and 90s, they took up minimal space in my carry-on. (Traveling in the winter would be a totally different story...)
So easy and breezy.
I've had my sights set on this Sndys pair for a while.
The strap on this is the perfect length and the color goes with everything I packed. No notes.
Tailored Shorts + Printed Tee + Loafers
The most comfortable loafers I've ever worn are these ones from M. Gemi—I'm not even exaggerating. I walked the whole day around the Forum, the Colosseum, the neighborhood of Monti, and all the way back uptown in them with zero blisters.
I brought this terrycloth shirt from Solid + Striped and these Everlane shorts to keep things casual for an entire day of getting my steps in.
Trendy shirt? Check.
I was looking for a pair of white high-waisted shorts for my vacation, and these did not disappoint. Just size down for the perfect fit.
Your feet are gonna be very happy with this purchase, I promise.
Breezy Long-Sleeve + Wide-Leg Jeans
On to Naples! This billowy top was worn on more than one occasion since you can wear it open or button it all the way up. I also rewore my favorite pair of Ética jeans since the wide-leg silhouette ensured the denim wasn't sticking to my skin in the heat, but I could also wear them in the evening when it cooled down. (I almost didn't bring any jeans at all, which would've been a massive mistake.)
Also, this pizza at Antica Pizzeria Da Michele high-key changed my life.
A similar style that feels a bit more elevated.
You always need a good pair of jeans that'll catch some breeze.
Swimsuit + Gold Jewelry
For the Sorrento and Amalfi Coast portion of the trip, I knew I would just be wearing swimsuits and bring some dresses that would double as a cover-up. This Onia bikini came with me, and I knew my go-to gold jewelry could be worn in the ocean without having to worry about anything coming off.
Nia Thomas' self-titled label has the most jaw-dropping swimwear pieces
Another swimsuit I brought with me with a gorgeous print.
The pearl detailing on this pair has my heart.
A sweet, everyday necklace that you never have to take off.
Cover-Up + Black Sandals
I got this oversize Ralph Lauren shirt from the men's section so I could wear it as a dress and throw it on over any swimsuit. It's honestly the best purchase I made for this trip.
This long-sleeve option works as a cover-up and something dressy to wear with tailored pants. The range!
Here's another striped option that's similar since it's linen and has short sleeves.
A flip-flop with ankle support—the best of both worlds.
Slide these babies on to complete any minimal look.
Bold Midi Dress + Net Bag
Once I saw this Dôen dress online, I knew I needed it. I threw it on over a swimsuit and brought my J. Crew net bag to fit some beach essentials for a day trip to Positano. Of course, what's a stop at Positano without checking out Le Sirenuse Hotel? I made a lunch reservation at its restaurant La Sponda to see the best hillside views of the town and get inspired by the interior design.
This olive green dress gives off the same cool girl vibes.
Cannot overstate how much this fit while still looking chic.
Slides like these pack flat and will save you so much room in your carry-on.
Lacy Tank + Buckled Sandals
Another Dôen purchase for yet another vacation outfit. This white tank from the label was so pretty and worked for both casual and dressy restaurants. I rewore my jeans with it and grabbed my favorite tan Hereu sandals to walk around Sorrento for the last night.
This design is also comparable with its square neckline and lace fabric.
My exact tank isn't available (I snagged it in an online warehouse sale), but this other style is pretty dang close.
Fisherman sandals are still going strong.
This pair makes sure your feet won't overheat.
Matching Set
This set from the brand Terry is one of my favorite summer purchases, so I had to fit it in my carry-on. I headed back to Rome since I had to fly out first thing in the morning, but not before grabbing one last drink in a piazza around Bar San Calisto and having the best tiramisu (possibly ever?) at Roscioli Rimessa.
Such a staple.
This bright pop of red is winning me over.
This post was previously published and has since been updated.
