Cheryl Shops

Ciao! I am back from 12 glorious days in Italy and am full of Aperol spritzes, pasta al frutti di mare, and gelato. (All totally delicious.) I will say, Italy in August is not for the faint of heart—temperatures were in the high 80s or low 90s every day, and I was sweating in places I didn't know I could sweat from, which made rewearing things a bit of a challenge. As I noted in my Substack, I packed for the entire trip in a carry-on, and I'm proud to say I wore everything I brought except one shirt and one skirt; I really should have packed one less pair of shoes (especially since I bought two new pairs, whoops), but overall, I was really pleased with what I brought. I tried to capture photos of all of my outfits, either out and about or in the full-length mirrors in our hotels, so I could show you how careful packing can pay off. Here's everything I wore on my trip to Italy.

Straight from the airport 

Pro tip: Stash the outfit you want to wear your first day in your carry-on, so you can quickly change into it and venture out into the city before you fall asleep in your hotel room and get totally jet-lagged. This was easy to do, as this matching set is very lightweight and packable. A crossbody pouch is a must for travel, and I was super happy with this one. 

OUTFIT DETAILS: Quince linen tank | Quince high-waisted linen shorts | Quince leather sling | Birkenstock Arizona EVA sandals

Sightseeing in Rome

I almost never wear tank tops—it's rarely warm enough for them in San Francisco, and my upper arms are not my best feature—but I'm happy to have them on hand for traveling, especially in summer. This skirt was very light and breathable (as you'll see, it's one of the few pieces I was able to wear multiple times), and my sneakers came in handy for the trek through Villa Borghese—I did over 20,000 steps on this day!

OUTFIT DETAILS: Toteme tank top | Etoile Isabel Marant skirt | Veja V-10 sneakers

Fancy dinner in Rome

The entire point of our trip was to celebrate a dear friend's 50th birthday, and she chose the restaurant at the Bulgari Hotel for the celebration, so of course I had to dress for the occasion. As dramatic as this dress looks, it actually packed very easily (it's silk organza) and breathed well. I only wore it once, but it was worth the room it took in my suitcase. 

OUTFIT DETAILS: Zimmermann dress | Fe Noel x Target bag (sold out) | Jambu sandals 

Travel to Amalfi coast 

People complain about how challenging it is to get to the Amalfi coast; we took a taxi to the Rome train station, a train to Naples, then were picked up by a driver and whisked to our hotel...after a 2-hour detour to his home in Sorrento, where his wife cooked us an amazing lunch complete with tomatoes from the garden, homemade mozzarella, and a lot of wine. I'm glad I wore a comfy outfit, although I wish I had gone for shorter sleeves.

OUTFIT DETAILS: Farysays top (no longer available) | Isabel Marant lecce belt | Free People linen shorts (current version) | Birkenstock Arizona EVA sandals

Day trip to Capri

We spent most of the day on a boat, so I am actually wearing a swimsuit under this linen dress, which I've had for a gazillion years (I think it's at least 10 years old). This was also the only day I wore these shoes—they are comfortable but not great on cobblestones. Also, I should note: you're not supposed to sit on this Vespa—there's a subtle sign, which I missed—but thankfully no one yelled at me!

OUTFIT DETAILS: Target hat | GAP linen dress (similar here) | Jeffrey Campbell shoes 

Day trip to Amalfi 

Once again, I am wearing a swimsuit under this dress, as I learned on our first day in the Amalfi Coast that afternoon dips in the Mediterranean are absolutely essential in summer. I had ordered this dress the week before we left and it arrived just in the nick of time, about an hour before we left for the airport. It's giving Isabel Marant, which I love, for a lot less—I'm a huge fan of this brand. 

OUTFIT DETAILS: & Other Stories dress | Birkenstock Arizona EVA sandals

Exploring Matera

We rented a car in Naples to drive to our next destination in Puglia and took a slight detour to Matera, which is one of the oldest existing civilizations in the world(!) and a Unesco World Heritage site. Highly recommend visiting if you ever get the chance—as you can see from this photo, it looks and feels like you're in another world—but definitely wear sneakers, as there are a ton of stairs and cobblestones. 

OUTFIT DETAILS: Anine Bing tee (current version) | Quince high-waisted linen shorts | Veja V-10 sneakers

Day in Alberobello

Also a Unesco World Heritage site worth visiting: the town of Alberobello, which is famous for its charming stone huts, called trulli. It's another town where comfy shoes are a must, however I saw a bunch of women all decked out in heels and body-con dresses (so Italian!). I wore almost the exact same outfit in Positano a few days earlier, with a black tee instead of white; in both cases, I was super happy I brought my packable straw hat, because this hillside town was bright AF (in a good way, of course). 

OUTFIT DETAILS: Target hat | Hanes tee | IRO skirt (recent version) | Birkenstock Arizona EVA sandals

Bicycling through Itria valley

This was one of my favorite days of the trip—we took a 20-mile e-bike ride through the countryside, ending up at a traditional masseria, where we had a huge (and delicious) lunch. I was glad I saved my skort for it, and sneakers were obviously a must. We shot this in Ostuni, a nearby whitewashed town, which is worth a visit for its amazing views. 

OUTFIT DETAILS: Very old H&M striped tee (similar here) | Aerie pleated skort | Veja V-10 sneakers

Day in Polignano a Mare

This was our last full day in Italy, and as you can see, I am scraping the bottom of the barrel in terms of outfits (I was miraculously able to wear this skirt a second time). This was also, by far, the hottest day of the trip—40 degrees celsius according to our car—and I really wish I had another tank top left! But highly recommend visiting this town; it was one of my favorites in Puglia. 

OUTFIT DETAILS: Madewell tee | Etoile Isabel Marant skirt | Birkenstock Arizona EVA sandals

Dinner in Monopoli 

I was so excited to wear this dress—it's from Sienna Miller's excellent collection for Marks & Spencer—and yet every night it was still way too hot...until our second to last night, when the temperatures dipped into the upper 70s (lol). I bought the shoes somewhere in Sorrento (I could not tell you where, except it was off of the main street), and no, they're not Hermès, although nearly every shoe store in the Amalfi Coast sells some sort of Oran knockoff. I ended up wearing these quite a bit, as they could accommodate my hot, swollen feet and were great on the cobblestones. More details coming in my newsletter this week!

OUTFIT DETAILS: Sienna Miller X Marks & Spencer Dress | Fe Noel x Target bag (sold out) | Sandals from Sorrento