What to pack for a summer in Italy as an almost-40-year-old woman (links included)

Written By Jacki Ochoa

Most of the “what to wear in Italy” TikToks you’ll see are geared toward people in their 20s. I’ll admit, much of what I wore was inspired by those looks—but not exact replicas. I’m a 38-year-old woman, and low-rise, barely-there styles just aren’t for me. Never were. Never will be.

Below, I break down some of my favorite looks and what made them essential for our summer trip to Italy.

Airport outfit

Let’s start strong with a solid airport outfit. The champion here is Vuori—but this outfit was chosen with extreme intention. I went with Vuori’s Performance Jogger because they’re comfy and cozy (made with their DreamKnit™ material), but most importantly, because they have a cuff at the ankles. If you’ve ever traveled, you know airport and airplane bathrooms can get downright nasty. I didn’t want the bottom of my pants touching the ground—especially since I’d be curling up in my Lufthansa lay-flat seat for many hours. I wasn’t about to let any gross germs crawl into bed with me 😜

Additional pieces: 

Sightseeing in Pompeii

Another must-have item on any trip is a good pair of walking shoes. For me, it was the New Balance 530 shoes. Everyone on TikTok will tell you to go with the Dr. Scholl’s Time Off Sneaker, but I bought those last summer—and even though I sprayed them with a good shoe protector, they got noticeably dirty after just one wear. I never wore them again.

The New Balance 530s, however, were comfy right out of the box. I didn’t break them in before the trip (not smart—I don’t recommend this), but my feet never got tired or sore. They were the only sneakers I brought, and I’m so glad I did!

Additional pieces: 

Dinner in Positano

I came out strong for our first night in Positano, but once again, the real star of the show was the shoes. Not because they were particularly stylish or chic, but because they were comfortable, looked great, and—most importantly—didn’t hurt my feet.

As many people will tell you, don’t bring heels to Italy. It’s true—especially on the Amalfi Coast and in Capri, where you’re constantly walking up and down stairs. These flat, strappy sandals with an ankle strap were perfect. I wore them in black every night of our trip.

Additional pieces: 

  • Sunglasses from Le Specs 

  • The earrings are from Madewell, but they aren’t online anymore. These are similar.

  • The perfect evening bag from Amazon

  • Cuff bracelet from Madewell

  • Skinny belt from Madewell

  • White linen cropped tank top from Reformation

  • White linen pants from Madewell (mine are petite, but they have regular and tall sizes too!)

Boat day

Everyone needs a good bathing suit, and for this trip, I brought seven—one for each swim day, plus an extra. For those of us who prefer not to wear barely-there bikinis, Cupshe is a great option. Every single suit I brought, including the one pictured above, was from Cupshe. You can also choose different sizes for the top and bottom. For example, I wore a large top and medium bottoms.

Not pictured—but equally essential for the Amalfi Coast and Capri—are a good pair of waterproof, sturdy sandals (you’ll be hiking to and from some beach clubs) and water shoes, since many of the beaches are rocky or pebbled.

Additional pieces: 

Dinner in Capri

It goes without saying that you’ll need some dresses. The one pictured above is from Reformation. That said, I actually would have preferred to bring fewer dresses and focus more on mix-and-match outfits (more on that below).

Pro tip: Avoid short dresses that could expose you if the wind picks up—it was surprisingly breezy at night. On the one occasion I wore a short linen dress, I had to hold it down the entire time to keep it from flying up.

Sightseeing in Naples

The biggest piece of advice I can give you is to invest in pieces that can mix and match—think several tops and several bottoms that can be easily paired in a variety of ways.

In the photo above, I’m wearing these Madewell shorts and this bodysuit from Express, but I also brought several additional pieces with me to create different outfit combinations.

Tops:

Bottoms: 

  • White linen pants from Madewell (mine are petite, but they have regular and tall sizes too!)

  • Linen-blend mini skort from Abercrombie & Fitch in white and black 

Packing for a trip—especially one you’ve been looking forward to for months and have high expectations for—can feel surprisingly stressful. That’s why I created my “wardrobe equation,” which I share in this blog to help take the guesswork out of vacation prep. (Fair warning: the process starts about two months in advance!)

I know the temptation is to buy an entirely new wardrobe for your summer vacation, but one of my biggest takeaways was this: invest in pieces you can mix and match, rather than one-off items like dresses. After a long, sun-soaked day, the last thing I wanted was to squeeze into something tight or wear something that didn’t work with a regular bra. I wanted comfort—but still chic, stylish, and easy.

Jacki Ochoa
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My “wardrobe equation” for stress-free vacation prep