We recently visited Italy for two weeks, and one of the most common questions I get asked is, “Where did you get that?” I spend a lot of time planning my outfits for these big trips, so I am always eager to share what I packed and what worked for me. I love wearing cute and comfortable dresses while traveling, and they are always so easy to throw on.
In case you’re reading this post several months later, we visited Italy from May 24th to June 8th. It was unseasonably cold in Tuscany during our visit, but other than that, the weather was very nice. You could basically get away with a dress and a jean jacket every single day. The average temperature was probably about 75 degrees (Fahrenheit) during our visit.
Before we get into the outfits, I want to talk about the shoes I wore on the trip. I wore this pair of wedges almost every day. They were so comfortable, and I didn’t have much trouble getting around in them. I also loved that they went with every single outfit. I always invest in a great pair of nude wedges to have for the summer!
Table of Contents
Day 0 – Travel Day
This is always my go-to travel outfit. It’s a super simple dress from Old Navy paired with a jean jacket from J. Crew. If you ever see me at the airport, this is probably what I’ll be wearing! Also, the hat is from Amazon.
Day 1 – Rome
This is another super simple and comfortable look for a day of exploring in Rome! We had the perfect weather for walking around, and I was never too hot or too cold. Note: If you are going to The Vatican, you will need to cover your knees and shoulders.
Day 2 – Tuscany
We picked up a car at the Rome airport and drove to Tuscany on our second day in Italy. The midi skirt I wore is from Francesca’s, but they don’t carry it anymore. I did link a couple other options below. Also, it was a little chilly and rainy, so it was nice to have a jean jacket as a layering piece. This jean jacket was 110% necessary thorough the entire two weeks in Italy! Don’t leave home without one.
Day 3 – Tuscany
Since it was a little chilly in Tuscany, I decided to go with a long-sleeve dress. We went on a wine tour, and I was very comfortable with this outfit choice! I didn’t feel like I was overdressed or underdressed.
Day 4 – Tuscany (Daytime Look)
The cold weather continued throughout our time in Tuscany (in late May), so I decided to go with a simple black dress and a jean jacket. On this day, we walked around the town of San Gimignano and did a cooking class at our hotel. I didn’t want to wear anything too elaborate or dressy since we would be cooking pasta. Also, I’m glad I didn’t wear a dress with sleeves since it got so hot in the kitchen!
Day 4 – Tuscany (Nighttime Look)
We ended up changing after the cooking class since we had a nicer dinner to attend this evening. I put on a long-sleeve dress because I knew it was chilly outside. We enjoyed some amazing cocktails on the terrace at Borgo Pignano before heading inside to our fancy dinner at Villa Pignano.
Day 5 – Tuscany
Our last day in Tuscany was spent at another winery near San Gimignano. We had terrible luck, as it rained throughout the entire wine tour. Regardless of weather, still had a great time and drank some amazing wines.
Day 6 – Florence
We dropped the car off at the Florence airport and did a ton of walking around the city. It was about 70 degrees and partly cloudy, so it was the perfect temperature to explore a new city and get lost. We fell in love with Florence on this trip, and I am already dying to go back.
Day 7 – Florence (Outfit #1)
We got up super early so we could beat the crowds at the infamous Cathedral (The Duomo). I love waking up early on vacation because you can get better photos without a bunch of people in the background! I wore two different outfits this day because I needed to cover my knees to enter the church. For my first outfit, I wore a midi skirt that I purchased from Francesca’s. They don’t sell it anymore, but I linked a similar option below.
Day 7 – Florence (Outfit #2)
I changed outfits after visiting the cathedral because it was gearing up to be a hot day in Florence. I wanted to be comfy for a day of exploring! This was the first day I decided to wear shorts on the trip. Old Navy has a ton of great options for shorts if you are looking for some new styles.
Day 8 – Cinque Terre
We spent the morning traveling to Riomaggiore in Cinque Terre. I ended up changing outfits once we arrived to our Air B&B. We were so sweaty by the time we climbed all the steps! I am glad we had time to freshen up and change outfits. If you have crazy/long travel days while in Italy, bring a change of clothes if you can.
Day 9 – Cinque Terre
On our second day in Cinque Terre, we did a pesto cooking class in Manarola overlooking the water. It was a beautiful setting to learn how to make fresh pesto. After that, we explored several of the other towns in Cinque Terre. This dress was the perfect option for a day of exploring!
Day 10 – Cinque Terre
We needed a day to just sit and relax, so we spent the entire day on the beach in Monterosso al Mare. It was the perfect weather to lounge by the water and read a book. We had some amazing local white wine while we soaked in the sun. It was a lovely day. (I purchased this kimono from Nordstrom Rack, but I can’t find it online. The brand is Love, Fire.)
Day 11 – Bellagio, Lake Como
It’s quite a ways from Cinque Terre to Lake Como, so we spent the majority of the day traveling (by train). I wanted to be super comfy while traveling, so I went with a simple black dress from Old Navy. I also put a cute and colorful headband in my hair to make the outfit pop a little bit.
Day 12 – Bellagio, Lake Como
Sadly, the dress I wore on this day is no longer available. This was part of the Vineyard Vines Collection for Target. I seriously went right at 8 AM when they opened so I could snag this cute little dress! I am going to link some similar options below, just in case you like the look.
Day 13 – Bellagio, Lake Como
On this day, we went truffle hunting and participated in another cooking class. It was a full day, but we had so much fun. I loved the truffle hunting dog, Pluto. He was so cute! Obviously, I couldn’t really wear a dress to go truffle hunting, so I busted out the shorts for this experience. I purchased these cute striped shorts from Old Navy. It looks like this color might not be available at the moment, but there are still plenty of other colors and styles to choose from!
Day 14 – Bellagio, Lake Como
We didn’t have any set plans for our last day in Italy, so we decided to take the ferry to different towns on the lake. It was a beautiful day outside, so I wore this cute little lemon dress. Lemons are everywhere in Italy, so I thought this was a very appropriate outfit choice.
I hope this helps if you were curious about my any of my outfits while we were in Italy. I love sharing all of my finds with y’all.
For more information on our Italy trip, check out my other posts linked below.
As always, let me know if you have any questions about anything you see in this post. I’m always happy to help!
Hi there!
Great blog!
Question: What size are you in the Imysty dress? I want to purchase it and I think we may be around the same size. I’m between getting the M or L.
Hi Karen – I actually got a small in the Imysty (the navy one w/ the white flowers). It is pretty forgiving overall so I would go with the Medium if you are debating between M and L.