Classic and Easy Outfits for a September Trip to Italy

Yesterday’s Italy recap was a novel…and today I’m back to discuss more about our trip. I promise I won’t be as long-winded this time.

What to pack for 12 days in Italy in September

I’m a chronic over-packer, and always stuff way too much into my tiny little suitcase. When we first planned our 12-day trip to Italy, I was a bit stressed as to what the heck I was going to bring. How could I possibly fit all of the essentials and outfits for Italy into my suitcase for such a long vacation?

I’m happy to report back that I packed pretty dang well for this trip…if I do say so myself. Most of my wardrobe consisted of casual outfits because we did a lot of walking on this trip. But, I was able to keep things stylish with neutral colors to have more of an Italian look.

Outfits for Italy – What I Packed

Here’s everything I packed for our September trip to Italy.

Italy Packing List

I also used my go-to packing cubes to keep everything organized and compact. These work so well if you’re an over-packer like me!

Italy’s Forecast in September

In the rain in Rome in September

The summer months were a scorcher in Italy with triple-digit temps and hardly any rain. Luckily, the heat was gone by the time we visited in mid-September and we enjoyed days in the 70s throughout our entire vacation. I was worried we would sweat the entire trip, but the average temperatures were so pleasant for this time of year.

Whenever I pack, I always check out the forecast to make sure I’m prepared. Knowing that we would see some rain, I made sure to pack my Patagonia rain jacket and an umbrella. This saved the day for us in Rome and it’s such a light jacket.

Day Outfits for Italy

I chose these white jeans, sandals, a crossbody bag, and a navy top for our trip to the Vatican. You have to be covered up (no low necklines, bare shoulders, or short skirts with their dress code), so I figured this was the most conservative thing.

Make sure you bring a maxi dress or pants if you plan to visit many of the Italian churches. You don’t want to miss out because you’re not allowed inside!

When we would explore during the days, I often wore t-shirt dresses, and sandals. Before leaving for our trip, I picked up about 4-5 of these easy breezy dresses from Old Navy. So cheap and didn’t wrinkle at all. These were great because I stayed cool, could walk around easily, and still felt put together with a cute outfit.

For our wine trip, I opted for a pair of shorts and this new top from Madewell that I absolutely adore. It’s a bit thicker material, so it didn’t wrinkle in my bag.

A swimming suit and sunnies were a must for our four days in Sorrento and exploring the Amalfi Coast. I also threw in some flip-flops and a coverup to make my journey to and from the pool a little easier.  

Comfortable Shoes Are A Must!

I only needed three pairs of shoes for our trip…sneakers, sandals, and a block heel for dinners out. During the day, you’re walking so much and you have to have comfortable walking shoes. I would take some time to find the best shoes before you leave for your trip.

These sandals were a lifesaver for me on our trip. I did a lot of research before choosing a pair of sandals because I wanted to make sure they had support and wouldn’t give me blisters. These feel like you’re walking on a cloud and I had zero problems. I walked many miles in them and they always felt great.

I also packed my straw hat and wore it constantly. This one is a great option because you can smush it in your bag and it still comes out looking just fine. It’s always a good idea to have a hat on hand to hide dirty hair and keep the sun out of your face.

Night Outfits

For the most part, we were pretty casual when we went out to dinner and everyone else was too. We did dress up a bit one night and I wore a simple black dress, my favorite nude heels, and my leather jacket

At night it would get cooler, so a sweater or jacket should be on your packing list! I wore jeans out a few times, and would just throw a cute blouse on top.

I wore a lot of dark colors in Rome & Florence, but since Sorrento was more of a beach town I wore a lot of white. This lace white dress is a favorite of mine (it’s super old, so I don’t have a link), and it worked out perfectly for a dinner on the water in Sorrento. I would definitely go for lighter clothes if you’re visiting southern Italy.

I ended up wearing just about everything I packed and didn’t forget any important items. I did run out of underwear on the last day…so make sure you pack plenty! Plus, I had a few spills and messes along the way, so it’s always good to have a few extra tops in your bag too. You should have seen the laundry when we got back. Oh boy!

Mix & Match Neutrals

Overall, it was nice to see that Italy was incredibly casual and for me, it was all about comfortable items I could mix and match. A lot of navy, black, white, and gray made it easy for me to mix and match pieces and different colors along the way.

Plus, staying away from super bright colors and statement pieces made me feel like less of a tourist and more of a European. Which is always a nice feeling when visiting a new destination.

Heading to Italy? Read These Posts!

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I visited Milan, Lake Como, and Venice during the late spring. Here’s my packing guide for those Italian destinations.



The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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