14 Days of Italian Summer Outfits

Now that summer travel is in full swing, I thought it would be the perfect time to share what I wore during our dreamy week in Italy.

From exploring the streets of Rome to sunset dinners in the Tuscan countryside, each outfit was curated with comfort, style, and the warm Mediterranean sun in mind.

Whether you’re planning a European getaway or just looking for warm weather outfit inspo, I’ve rounded up 14 easy and chic looks that will take you from city strolls to vineyard views, no packing stress required.

Italian Summer Outfits

Day 1: Sightseeing in Rome

For a full day of walking around and exploring Rome in the summer heat, I kept it light and comfy with these taupe linen shorts and a breezy knit tank with cute front cutouts. It gives the perfect balance of functional and flattering.

I threw on my Miu Miu sneakers for extra comfort and paired the look with a neutral cap (any hat would work), sunnies, and my go-to Jodi small bag. This outfit is super easy to move in and still feels put together enough for sightseeing or grabbing a bite to eat in the city.

Day 2: Romantic Dinner in Tuscany

There’s something so magical about golden hour in the Tuscan countryside, and I wanted an outfit that felt just as dreamy as the landscape. I went with this strapless cream maxi dress that flows beautifully with every step. And yes, it has pockets! It’s the kind of piece that feels elevated without trying too hard, making it perfect for a summer date night.

To keep the look soft and romantic, I accessorized with a pearl embellished raffia bag, matching raffia sandals with a little heel, and a delicate pearly necklace.

I also added a touch of glow with this shimmery gold body oil, which caught the sunset light in the prettiest way. I finished the look of with my Miu Miu sunnies for that effortless “I just threw this on” kind of vibe.

Day 3: Bike Ride in the Tuscan Hills

For a laid-back day of exploring the countryside, I kept things simple and breezy. The blue and white striped boxer shorts are not only adorable but super lightweight, making them perfect for packing and even better for pedaling through the hills. I paired them with a crisp white linen button-up that adds a polished touch while still feeling relaxed.

Comfort was key, so I threw on my Miu Miu technical sneakers and topped things off with a Celine ball cap and Quai sunnies to keep the sun out of my face and my skin protected.

A small Prada crossbody made it easy to keep my essentials close without weighing me down. This is one of those outfits that looks cute in pictures but is also super practical, truly the best of both worlds!

Day 4: Cooking Class to Dinner Date

This little white eyelet dress was the perfect pick for a day that started with a cooking class and ended with a cute dinner date. The cinched waist gives such a flattering silhouette, and the delicate eyelet details add the prettiest feminine touch. It’s lightweight, breezy, and transitions so effortlessly from daytime plans to a casual romantic dinner.

I styled it with my go-to Sezane gold sandals (I seriously can’t travel without them!) and the woven Sezane basket bag that goes with just about everything. A swipe of shimmer body lotion gave my skin a beautiful glow, and Miu Miu sunnies finished off the look. This outfit felt very “Tuscany in the summer.”

Day 5: Rooftop Hangs in Florence

For a golden hour rooftop moment in Florence, I wanted something that felt effortlessly chic but still had a little edge. I went with this black loose knit tank and tucked it into pleated white linen trousers. They’re structured but breathable, which makes them ideal for warm summer nights.

I kept the base simple but brought the glam with all the accessories. The gold woven shoulder bag, gold buckle belt, and my go-to body shimmer oil added just enough sparkle to make the look pop without doing too much. I finished the look off with black platform thong sandals and my Celine sunnies, the perfect combo for cocktails and views.

Day 6: Sightseeing to Dinner Date

When traveling, I’d venture to guess that you have quite a bit of sightseeing on your itinerary. For those outings, a comfortable outfit that can take you from day to night is crucial, and this combo fits the bill.

I love that these longer, trouser-style bottoms offer more coverage than your typical shorts. I added a simple tank on top, defined my waist with a belt, and slipped into my tried-and-true sneakers. This look is the perfect example that you don’t have to overcomplicate your outfits.

Plus, because each of these pieces has a high-quality look, you could easily wear this out to grab food or drinks after a long day of tours and activities.

Day 7: Sightseeing in Florence

Can you tell I’ve been loving the long short trend lately? They make for such a practical and chic bottom choice and they’re easy to pair with a variety of tops while traveling. And because of their length, they feel more appropriate to wear to a dinner than something that’s too short.

This embroidered top made the prettiest complement to these black bottoms. It was a breathable pick that looked elevated while maintaining a high level of comfort.

Now let’s talk accessories! This hat makes a big statement and really pulls your focus to the top portion of my outfit rather than the laid-back lower half. It also adds a good dose of texture and shape. Take this as your sign to incorporate more accessories in your looks, whether you’re traveling or not.

Day 8: Train Ride & Winery Lunch

You can never go wrong with a monochromatic look, and it’s an especially appealing choice when traveling because it takes the guesswork out of getting ready.

Here, I styled a pair of high-rise shorts with a simple vest and sneakers (yes, once again.) The shorts have a crepe fabric which made them look and feel a bit more luxe than cotton or even linen. This outfit was easy to throw on and could have worked for a variety of occasions during my trip.

Day 9: Anniversary Dinner Outfit

Because we took this trip to celebrate our anniversary, I had to pack a few items that felt particularly “special.” This floral maxi dress was my top choice, and I’m so happy that I wore it on one of our date nights.

The floral print paired with the navy blue base makes for such a pretty mix. It fit like a glove in the best way possible and would make for such a chic wedding guest dress look as well. Just add heels and a purse and you’ll be set for a celebratory evening out!

Day 10: Dinner Date in Positano

Another dress that I packed for those more special outings? This bright red pick! The tiered silhouette and ruffle detailing make it such an eye-catching outfit choice. I love that the shape of it offers tons of dimension and visual interest too, meaning you can opt for more simple and toned-down accessories to keep things well-balanced.

This dress is currently on sale (and it’s going fast), but I’ve linked some similar options below in case you want to explore more options!

Day 11: Arriving in Sorrento and Heading to a Farm-to-table Meal

No trip to Europe would be complete without a good mix of Sezane style selects in your luggage. While there are loads of picks I love from the brand, it’s staples like this striped button down shirt that I really adore.

For both casual and more polished occasions, this top could serve as a fun focal point in your outfit. I paired it here with some basic linen shorts but you could also style it with a white silk maxi skirt and some heels.

Also, comfy sandals while traveling are a must. Need some recs? I’ve listed the comfiest shoes to wear in Europe in this blog post.

Day 12: Boat Day in Capri

This might just be my favorite look from the entire trip (which is saying a lot!) It’s simple, laid-back, and very summery, but that’s what makes it such a great go-to if you’re spending any time by the water this season.

These balloon-style pants serve as a neutral base layer while the colorful silk scarf top totally pops. The hues in my top also complemented the turquoise waters (making for the prettiest photos along the way.) I had my swimsuit on underneath this outfit!

Day 13: Patio Date Night

Coming in a close second for my favorite Italian vacation look? This combo! Would you believe me if I told you this statement skirt was from Amazon? I was absolutely floored when I came across it and was even more impressed when I received it and felt the quality. It looks like a piece you’d find at Saks Fifth Avenue or Neiman Marcus.

I wanted to keep this look neutral so the skirt could really do its job and shine on its own. To make sure it was the star of the show, I paired it with a basic white tank, brown sandals, and a raffia bag.

Day 14: Sunset Dinner

To end things strong, I closed out our trip in this adorable matching duo. I ordered this well before our trip and styled it a few different ways while I was back home. However, it felt particularly fitting for Italy — especially for a sunset dinner by the water.

The print is fun while still maintaining a more neutral look. I also love that the top and bottom have a scalloped edge. I slipped into my white sandals and once again kept my accessories minimal so I could let this duo make a statement on its own.

Which Euro summer look is your favorite? Let me know in the comment section below!