Classic and Easy Outfits for a September Trip to Italy
Heading to Italy in early September? Here’s my packing list for the warm days spent exploring and sightseeing in this gorgeous country.
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.

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 fit in with the Italian fashion.
Outfits for Italy – What I Packed
We had a 12-day trip from central Italy (Rome, Florence, and Tuscany) down to southern Italy (Sorrento). We visited in mid-September and it was a wonderful time to go. Sunny weather, but not unbearably hot and not too cold or rainy. I packed efficiently, but with enough items that I would be prepared for a variety of weather conditions.
Here’s everything I packed for our September trip to Italy.
Italy Packing List
- Suitcase (this is the best luggage in the medium size)
- Everyday Sneakers (must have a comfortable pair of shoes)
- Comfy sandals (these were my lifesaver)
- Block heels
- White shorts & denim shorts
- Pair of jeans & white jeans
- Pajamas (my go-to pair)
- Wide-brimmed hat (loved wearing this on dirty hair days and sunny days)
- Crossbody bag or leather sling bag
- 4-5 tops (including tank tops)
- Sweater (it’s all about layers when you pack!)
- Leather jacket or denim jacket
- Swimming suit, coverup, & flip flops
- Day dresses (these budget-friendly ones did the trick)
- 2-3 dresses
- Athletic wear (one legging outfit)
- Socks, underwear, bras (I brought this in black and nude…the best bra ever!)
- Scarf
- Patagonia Rain Jacket & travel umbrella
- Sunglasses
- Travel Adapters (don’t forget to buy a few travel adapters. You will need Type L for Italy)
- Refillable Water Bottle
- Accessories (sunglasses, necklaces, earrings, etc.)
- Insect repellant
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

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 for rainy days.
Italy Outfits For The Daytime
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 and a light sweater or shawl if you plan to visit many of the Italian churches or religious sites. You don’t want to miss out because you’re not allowed inside!


When we would explore during the days, I often wore cotton t-shirt dresses and sandals. Before leaving for our trip, I picked up about 4-5 of these light dresses from Amazon. This summer dress is inexpensive and it doesn’t wrinkle. 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 Footwear Is 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 for the cobblestone streets. I would take some time to find the best shoes before you leave for your trip.
These comfortable 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. It was nice to have for cooler evenings.

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 during the warm weather.

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 local. Which is always a nice feeling when visiting a new destination.
Heading on an Italian Vacation? Read These Posts!
- Recap of our 12-day trip to Italy visiting Rome, Florence, and Sorrento
- Travel tips to make the most of your time in Italy
- International Travel Favorites
- Milan, Lake Como, and Venice Travel Guide
Heading to Northern Italy For Your Next Trip?

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

Huggies //ย ย Packable Hatย //ย Water Bottle //ย Green Sunglassesย //ย Comfy Sandals //ย Everyday Sneakersย //ย Sling Bag //ย Denim Shortsย //ย Best Braย //ย Swimming Suit //ย Cozy ‘Denim’ Jacketย //ย Travel Adapter //ย Suitcaseย
Casey




