We’re back! Andrew and I celebrated our ten-year (delayed by a year) anniversary in Italy—a place I’d never been, despite being nearly 100% Italian in my heritage. And man, this trip was one for the books.
I did a whole solo podcast episode on the places we visited in Positano (Amalfi Coast) and Rome, and while by no means an exhaustive itinerary, it was pretty damn good. haha.
Andrew planned our entire trip, which was just under a week, and I feel like we hit so many fun things without feeling like we were overbooked. So if you want travel rec’s including hotels, restaurants, and activities, listen below!
But today we’re talking fashion—specifically, carry-on fashion.
I didn’t want to risk losing luggage since we were immediately leaving for Positano by car after our flight landed in Rome. So I committed to packing carry-on, and it worked!
The goal was to have a mix of a few fancier looks for nice dinners, with mostly chic, simple daily wear that I could get around town in. I think it worked perfectly!
Listen, you guys know I’m not a fashion blogger, but I can throw together a look where the key vibe is comfort. I know some people prefer rocking a heel and sexy look no matter what, aaaand… I’m not one of them.
So check out some picks below that were versatile, chic and most importantly comfortable. Because who wants to be messing with clothes on the trip of a lifetime?!
All items from Left to Right, Top to Bottom
This was the most-worn item I brought, hands down. This was cute on its own with jean shorts and cute flat sandals, over a bikini poolside, or thrown over top of a long dress at night (tied up at the waist) with a long dress. So versatile and chic! Unfortunately the one by Stillwater that I got is only showing now in black, but here’s an option in white.
The perfect travel gear. This one is by Girlfriend Collective, and the quality is great. I got it in black, and wore a white button-down over top of it for travel. I also wore these leggings for our bike tour around Rome, and of course for the flight home as well. As for the top, I also paired it with my faux leather shorts for a walk around Rome—super cute!
This was perfect for a night out in Positano, paired with a chic flat sandal. Unless you are extremely balanced and brave, I do not recommend heels for Positano! Hills and cobblestones = sprained ankle! We don’t need that on the trip of a lifetime now, do we?! (More shoe talk below.) My dress isn’t currently available online, but this one is similar:
I got this dress in an olive green color that isn’t showing now on the website, but I also love the vibrant shade of this one. I wore this for another dinner, and it was super chic and comfortable with pretty flat sandals:
This pairs perfectly with the black faux leather shorts, the black pants and the jean shorts. The ultimate versatile, chic piece.
I ended up wearing these with the Girlfriend Collective black tank top for a walk around Rome. Definitely a little sticky with the heat, but it wasn’t that bad! I love that you can wear these during the day with sneakers, or wear them at night with a more dressed-up shoe. Mine aren’t for sale anymore, but here are two versions that would work, one faux and one real leather. Here’s an option in real leather.
I am in love with the Agolde Parker jean short, which is short enough to be cute, but not so short that you feel exposed at any point. I wore these for our day-long cooking lesson/party, on the boat ride to Capri (brought a long cover-up/dress, but ended up going for comfort instead!), and paired with the white button down just to walk around the resort in Positano.
If you follow me on Instagram, you might remember my struggle to style this vintage Gucci skirt. I fell in love with it when I came across it at The Real Real in Dallas, and immediately knew I wanted to wear in on our Italy trip. I crowd-sourced some suggestions and ended up pairing it with the white button down, tied up in the front, and some cute mint Vejas sneakers. It was the perfect outfit to tour the Vatican, and if we had stayed longer I would have found another occasion to wear it. Here’s a similar skirt option that would look cute styled the same:
It’s chilly in May in Italy during the morning and evening hours, so I threw this over my shoulders for both breakfast and dinners. The tan color went with everything, and it packs really well since it’s cotton. Mine isn’t available for purchase anymore, but this one is very similar:
Guys, Target is IT for the basics. I’m telling you! I brought two of this style, in both white and ruse (not available, but a similar color is shown), and I wore them with jean shorts. Would also be cute with your button down tied on top, or your jacket thrown around your shoulders. Easy to dress up, easy to keep casual. And they wash really well!
These were great for nights at dinner, paired with either the sleeveless bodysuit or the tanks and jacket; I wore them with the bodysuit when we went to the Italian Open.
Fit note: These pants sit higher on the waist and hit right at the ankle. And because of the fabric, they don’t tend to wrinkle and I think the cut is just super chic.
Honestly, I reach for these at home all the time too; they’re a must-own in my opinion!
This top is great for a daytime excursion; I wore this during our day trip to Capri. It’s super lightweight and went perfectly with the jean shorts. Right now it’s on sale!
This button-down by Xirena was a great cover-up for chilly mornings, and I also wore it as my coverup for the flights both to and from Italy. The fabric is a little thicker than the white button down, and because of that I reached for it quite a bit. I even wore it on our early morning bike tour of Rome (highly recommend!), since it’s quite chilly in the mornings in May.
This can double as a dress or just make a chic coverup as you walk around the resort. Although I ended up going with jean shorts and a shirt for our day trip to Capri, I could have worn this as well.
The one I brought is unavailable for purchase, but this one is similar. Some more options below!
All items pictured in above collage.
A mom friend was wearing this recently and I knew right away that it would be perfect for our trip. It can be worn fanny pack-style around your hips, or slung over one shoulder for a crossbody look.
Though they also make this in cream or black, I fell for the multicolor which I thought gave it a little extra pop. It went well with every outfit I brought, whether casual or more dressy, and the leather is super supple and molds well to your body. I can’t say enough about this bag; it really was the perfect purse for this trip!
A note about shoes: Do not—I repeat, do not—make heels your go-to shoes for these two cities, unless you’re a total glutton for punishment! The hills and cobblestones of Positano are not designed for heels, and now that I think of it, it’s kind of the same in Rome. Lots of cobblestone streets, uneven walking surfaces, etc. I maybe saw three pairs of heels total on women between the two cities. So bring your cute, comfy flats and sandals!
I searched high and low for a white sneaker chic enough to wear with skirts, but casual enough to pair with my shorts outfits. This Vejas pair hit the mark!
They come in a ton of colorways—see here—but I ended up going with a mint contrast that I thought added the perfect contrast against the white sneaker. I think they looked great with all the clothes I brought!
One note about sizing: I’m usually a true 10, but these felt a bit tight. I thought they would loosen up as we walked, but they really didn’t. I’d at least try a half size bigger if you’re going to buy. Mine are by no means uncomfortable, but I do wish I had tried a half size up.
I bought this gorgeous pair of Grear sandals from Sarah Flint for the trip, and I can’t tell you how comfortable they are. The straps are thick and actually stay up—a huge problem with other gladiator sandals—and the sole has some cushion for walking.
The ones I brought along are literally 13 years old (!!!), but I’ve rounded up a few options from low- to high-end below. I wore these with my dresses for nights out, and they can also dress up any jean shorts outfit. These are a must-bring! They add a little dressiness but keep you comfortable.
You can’t remember everything! That’s why there is one item that I bought while there that I forgot to pack—a sweatshirt. I picked up the below sweatshirt in Positano because I love a good cheesy souvenir moment, and this one was super cute.
If you’re going in June, July or August, when it’s warmer, you might not need this extra layer, but I’m so glad I picked it up!