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 (fingers crossed!).

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.

Outfits for Italy – What I Packed

Here’s all of the clothing 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

This summer was 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 temps were so pleasant….we really lucked out!

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!

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), so I figured this was the most conservative thing. Make sure you bring a long 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 kinda put together. 

For our wine trip, I opted for white 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 4 days in Sorrento. I also threw in some flip-flops and a coverup to make my journey to and from the pool a little easier.  

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 even though it was such a pain to bring (couldn’t stuff it in my suitcase, so had to bring it on the plane with me. Ugh), I’m happy I brought it. It kept the sun off my face, but more importantly, it hid my dirty hair. Ha!

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 ended up wearing just about everything I packed, which is a first for me! 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 along the way. Plus, staying away from super bright colors made me feel like less of a tourist and more of a European. Which is always a nice feeling when visiting a new destination.

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The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m married to Finn & mom to Rory and Ellis. Together we’re creating our dream home in Chicago, one DIY project at a time.