italy outfit
Here I am on the first day arriving in Venice. I rolled up this Anatomie dress in my carry on and changed into it at the airport. It worked so well! 

We had so much fun exploring Italy on a recent trip to Venice, Florence, Rome, Sorrento, and the Amalfi Coast. My husband Philip and I traveled with two couples that are close friends of ours. We were part of a larger Rick Steves tour group of about 25 people. We had anticipated this trip for several months, and even though most of the planning was taken care of by our tour guides, the question still remained, what are we going to wear in Italy??

our packing strategy

My friends Rene, Wendy and myself really put our heads together to come up with our style strategy. We normally have a very casual lifestyle, so we were so excited to wear sundresses almost every day on our trip! These factors influenced our fashion choices: we were committed to packing in a carry-on suitcase, we had to cover our knees and shoulders when touring churches, we knew we had to pack for hot weather, and comfortable shoes were a must for touring around. Other than these factors, we didn’t know what to fully expect from our tour and the cities we were visiting. The following chronicles my “hits and misses” in what I packed on this amazing trip to Italy!

rick steves luggage
This is my Rick Steves suitcase and carry-on. I loved packing in a carry-on and not having to check a bag!


My shoe choices:   I packed Mephisto “Helen” sandals in a neutral metallic color (neutral metallics go with everything!), Cole Haan white sneakers, Vince Camuto woven pointy toe mules, and Madewell ankle wrap sandals. My Mephisto sandals and my sneakers were what I wore during the hours of walking tours. We logged anywhere from 5 to 10 miles of walking a day, and these shoes were cute with my outfits and comfortable! I was thankful I threw in the mules and wrap sandals last minute, because I ended up needing them to elevate my outfits for the evening. (more on that later)

Shop my travel shoes:

what to wear in italy, travel dresses
Rene, Wendy and I on the island of Burano, near Venice. These dresses were soaked through with sweat by the end of the day! Notice my cute travel purse and Mephisto sandals. Hats were also a must in the blazing sun!

Harper Cross Body Travel Purse: Wendy, Rene and I all bought this same travel purse in different colors. It’s a cute shape with a tassel, and it holds a phone, passport, credit cards, sunglasses and a lipstick! It even held our tour listening devices so we didn’t look quite so touristy!

Day Outfits:  I was happy, for the most part, with the day outfits I packed for touring around. My midi skirts were cute and appropriate for when we toured churches, I liked my sundresses, and I also packed skirts and tops to mix and match. These day outfits were especially perfect in Venice, Sorrento and on the Amalfi Coast. These areas feel more like people are on a holiday, and my clothes had more of a vacation getaway vibe.

vatican city travel outfit
At the Vatican. I had an off-white shawl to cover my shoulders, and this midi skirt covered my knees which made it church appropriate!
travel outfits in florence italy
These outfits were fun for a walking tour of Florence and an Italian cooking class. Notice the comfy shoes with our dresses!

misses (or how I’ll pack differently next time):

The impact of the heat:  While in Italy, we had temperatures in the high 90’s with high humidity. We were leaving the Seattle area where our temperatures were still in the 60’s and 70’s, so it was hard to realize how the heat would affect our outfits. I originally pictured us being with our tour group and not necessarily having a chance to change clothes before dinner. I pictured wearing my day dresses out to dinner or dressing them up a bit for the evening.

It turned out that we HAD to change clothes because we completely sweat through them!  Especially in Florence and Rome, the women are so stylish and sophisticated, we felt under dressed at night. We were kicking ourselves for not packing fancier evening outfits! It was a dreaded fashion missed opportunity. Like Tim Gunn says, we had to “make it work.” We pieced together night out outfits from what we brought to wear during the day. We looked fine, but what we came up with wasn’t what we would’ve worn if we had planned date night outfits beforehand. Bummer!

date night outfit, italy travel outfit
This is an example of my “make it work” evening outfit. This top and skirt were meant to be worn during the day with other pieces. I put them together with my woven pointy toe mules, so I felt dressed up enough! This rooftop restaurant in Florence was so beautiful!

I did discover a fun store called Twinset and bought a floral maxi dress to wear out in the evening. I love it, and I was able to wear it out in Rome and Sorrento. This pretty maxi dress really saved the day!

This Twinset maxi dress was so fun to wear out at night! My sweaty day outfits were getting tiresome!

The culture of each city:  Next time I go to Italy, I’ll have a better idea of how to dress in the different cities. In general, the Italian women are much more dressed up and stylish that what we see in the Pacific Northwest. What I packed tended to fit in more in Venice, Sorrento and on the Amalfi Coast. My sundresses, romper and skirts were more along the lines of these destinations with water where people are relaxing on vacation (think California, Florida or Hawaii).

Florence and Rome are definitely bustling cities where you would want to dress as if you’re visiting a city like New York. Knowing this, I wish I would have brought a dressier (but still comfortable) flat shoe. The Italian women were wearing stylish, dressy flat sandals everywhere. Flats are a must because of the uneven cobblestone streets and amount of walking one has to do in the city. I also wished I would’ve packed more sophisticated dresses and/or a cool jumpsuit for the warm summer nights going out to dinner and walking around the city.

travel dress, travel outfit
Here I am wearing my romper and feeling under dressed shopping in Florence. I would have felt totally fine shopping in this outfit while in Sorrento!
aritzia dress, italy outfit, italy travel
In Sorrento wearing my Aritzia dress and woven mules. Turns out I needed more dresses like this while it Italy!

In conclusion, leave your casual shorts/t-shirts/tanks at home and pack your sundresses for day and dressier outfits for night. Pack a variety of flats – more casual sandals/sneakers for day, and an elevated sandal for night. Even though I had a few fashion regrets, I had the time of my life in Italy! My purpose in writing this is to share my “hits and misses” and help you pack in order to be your stylish best self while visiting Italy in the summer. Julie is planning a trip to Italy in September. You better believe I’ll be helping her plan her outfits! Hope this helps!


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  1. Popping over from the FF newsletter!!
    It’s nice to hear your thoughts about this Krista!! I always think it’s good to evaluate what we packed to learn from it for next time. Of course, I always overpack. And joke that I can always buy things too. Like that maxi dress which is gorgeous!!

  2. Isn’t Italy magical? And you did it just in time last year 😉

    If you love hiking, I recommend a week of Italian Alps. I did it with an adventure outfitter located in England. Our guide is most attentive. The daily hike was intermediate level, challenging but not exhausting. Every lodging was terrific (your luggage was delivered while you hiked). The scene is quite different than Swiss and French Alps (including all the towns we stayed). After that, I took a local but to the nearest train station traveling to Venice, Florence, and Rome (each city for a week stay). Other than the hiking (with a small group of people from all over the world), I did the rest by myself. I was telling my mother last night about the privately catered Florentine steak dinner I had in Florence and saw this post now. It sure brings back a ton of fond memory.

    1. Wow! I can’t even imagine how amazing that would be! Definitely adding that to my list of trips to consider. I love active trips like that. Are you from England? –Julie