An Italy vacation is always exciting, no matter what time of year you plan to visit! We’ve traveled everywhere from the Italian Alps to small Tuscan towns, and larger cities like Rome, Milan and Venice. Once your trip is planned, the tricky part is figuring out what Italy outfits to pack. Everyone obviously has their own style. Hopefully, this Italy outfit trip guide will give you some inspo, whether you’re visiting in summer or winter!
Planning Your Vacation in Italy
Large Cities: Italy is full of iconic and historic cities. Some of our favorites are Florence, Venice, Rome, Verona, Naples, and Bologna. If you are at the beginning stages of your travel planning, make sure to read our complete Italy trip guide.
Amazing Small Towns: While the cities are great, we are really drawn to the small Italian towns more than anything. Many of our favorite memories have been visiting places like Montepulciano, Ischia Island, Cortona, and Pienza.
We also just spent the summer on Lake Lugano, and fell in love with the tiny village of Albogasio-Oria.
Must Try Specialties: You’ll surely enjoy endless pizza and pasta on your Italy trip. However, make sure to taste all the regional specialties as well.
For example, the area of Tuscany we were in last had Wild Boar Ragu! Naples is all about the Genovese, and in Florence we tasted unique tripe sandwiches.
How to Get Around: Many travelers will fly into a major city, spend a couple of days, and take off on a road trip from there. We personally use Discover Cars whenever we’re looking for a deal in Europe.
In fact, we’ve gotten rental cars for as low as €10 a day! The trains are also a great option to get around Italy. We wrote an entire for how to travel through northern Italy itinerary by train. Take a look on Omio to compare the different routes and companies.
Iconic Italian Experiences: This definitely depends on where you’re going in Italy. Still, it’s a good idea to book the most iconic experiences in advance.
A few of our favorites activities are wine tasting is Tuscany, a cooking class in Florence, and exploring the Milan Duomo rooftop. Also, consider jumping on a boat trip in Capri, ham tasting in Parma, and a Naples Street Food Tour.
Cheap Flights: This tip is specifically if you are coming from a far distance internationally. It’s often drastically cheaper to fly into one of the larger main cities and take a train to your final destination.
Our favorite way to start our trip planning is to check Skyscanner for flight deals. This website saved us $300 each on our recent family trip to Naples! We figured out we could fly direct to Rome, and jump on a fast train to the south from there.
10 Italy Outfits For Your Next Trip
1. Italy Outfits for Travel Days
Depending on where in the world you are coming from, you could very well be on an overnight or long haul flight. This means you need a comfortable airport outfit so you can get some sleep, and arrive ready to hit the streets of Italy.
I don’t know about you, but there is no way I am going to wear something for up to 24 hours of traveling, and then again to start my holiday! Typically, I have one Italy trip outfit of loose fitting pants or sweats with a warmer top and shirt underneath. This helps with the weird temperatures that can be inconvenient on long flights.
With that said, you might want to think of comfortable Italy outfits for the rest of your time traveling. This is especially helpful if you will be hopping on and off different trains, buses, or taking long car rides.
2. City Exploring
There are different clothes you might want for your days and activities in Italy. The first outfit is what I call “casual exploring.”
This entails shorts, a nice top or tank, and very comfortable walking shoes. If you travel to Italy with nothing but high-heals, then you probably won’t be walking too far!
These Italy outfits are perfect for days where you are really planning to do lots of steps. Part of your day may include hiking to the top of town or castle for amazing views. Maybe you’re considering a long coastal walk, or simply trying to experience as much of a large city as possible.
I’m usually team dress in Italy, but adventure casual is definitely is needed at some points. Remember this is Italy outfit inspo after all! So even if you’re just in shorts and a t-shirt, it’s best to have something that’s semi-nice looking.
We were just in Florence and I don’t think I saw any women in yoga pants, or the type of activewear that’s common in the United States.
3. All the Dresses
A nice flowing dress always should have a spot on your Italy Summer outfit list! Both long and short dresses are my go-to if the weather is looking nice on our visit. This is definitely true if you are anywhere near the coast or countryside of Tuscany.
Here’s one thing that I hate to say, but absolutely have to. Before my most recent trip, I read that only tourists wear lemon patterned dresses and clothing in Italy. At one point, I found the cutest dress with lemons on it, but decided to skip it.
Honestly, you should pack and wear whatever makes you happy. I will say if I did buy that Italy outfit, I would have been one of the many who had something similar on!
If you’re packing winter Italy outfits, you can pair darker or thicker fabric dresses with stockings and boots.
4. Italy Outfits for Hiking
Getting out into nature on your Italy vacation? Then you’ll totally want to add some hiking clothing to your packing list!
The Dolomites have become one of the most famous hiking destinations in the world, so we wouldn’t be surprised if it’s on your itinerary. You’ll want to bring a warmer layer for northern Italy even if you’re visiting in the summertime.
Remember that the weather can still be chilly during this time of the year at night up in the Alps. This also applies to popular destinations like Lake Como and Lake Lugano.
5. Night Out on the Town
It’s common for dinner to start somewhere between 8 and 9pm (or even later) all around Italy. Many restaurants might open at 7pm. However, know if you go this early, you’ll likely be one of the only people there if it’s not packed with tourists.
Either way, it’s smart to pack some Italy outfits for the night time. Fancier dresses, skirts, and dressy shorts are all common.
6. Swimwear & Coverups
Italy has so many great places to swim if you want to! You can jump in the lakes in the north, hit the beach along the Mediterranean coast, or even book a hotel in Tuscany with a massive pool.
What about specific winter Italy outfits when it comes to swimming? Well, if you didn’t know, Italy also has an abundance of hot springs!
We found amazing thermal hotels on the island of Ischia. In Tuscany, you can also visit some of the most beautiful (and free!) natural spas in the world such as the Saturnia Hot Springs.
7. Italy Outfits for Spring
Let’s get into a little more of the seasonal specifics. Spring is actually my favorite time to be in Italy. The winter has passed, everything is in bloom, and the crowds haven’t arrived yet.
You will need the everyday Italy outfit inspo that we discussed above with some slight alterations. For dresses, it’s nice to pair it with a light sweater and layer up a bit.
It can be rainy during spring in Italy, so it’s good to have a waterproof jacket or umbrella with you while exploring. Colors this time of year are what you might commonly associate with spring. Think about light blues, pale yellow, plush, and cream.
8. Summer Italy Outfits
As we mentioned, we were just in Italy this past summer. Visiting the country in these peak holiday months can be intense.
We didn’t realize that a lot of local places close for the month of August to go on holiday. We’ve also noticed it’s when the most Americans visit because they’re also on summer holiday.
If you’re taking a once and a lifetime to trip Italy and your only option is Summer, then go for it. Nevertheless, there are some things to be aware of.
First of all, it’s going to be hot! Plan for the heat when putting together your Italy trip outfit list. That means loose fitting clothing, breathable fabric, and nothing that will look terrible covered in sweat.
Bring a large hat to protect you from the sun, and of course a pair of shades. You’ll have some reprieve with the ocean air along the coast, but still plan accordingly.
9. Fall Italy Outfit Inspo
After spring, fall is our 2nd favorite time to be in Italy. The weather (and sea) can still be warm, large crowds have left, and there are plenty of long sunny days to enjoy.
The cities are full of life with everyone returning from their summer vacations, and the weather is cool and crisp. It’s also harvest season in Tuscany for wine lovers!
Something to note is that you wouldn’t wear the same fall colors as you might in the United States. Go for white, black, beige, grey and olive green for your Italy outfits this time of year.
Pair shorts with a thin jacket or pants and a light sweater. Fall is more about packing for all weather. The sun may be shining bright in the afternoon, but it can cool down drastically at night.
10. Winter Italy Outfits
Finally, how about some Italy outfits for winter> No matter where you go plan for cooler weather and possibility of snow. You’ll want a warm jacket, scarf, hat, and layers.
Popular colors this time of year are black, camel, grey and navy. While we have visited Italy once in the winter, it’s not the time we normally travel here. It will be cold and there is also a high possibility for rain in many places. Pack accordingly!
Have any questions about this article or want to share more Italy trip outfit ideas? Leave us a comment below!
Safe Travels,
Brigitte & Jake
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We’re Brigitte and Jake! American travel bloggers currently based in Spain. If you can believe it, we started Nothing Familiar way back in 2015 on an Ipad in the Ecuadorian jungle. Ever since, we haven’t stopped traveling! We’ve now been to over 60 countries around the world, with our expertise being Europe and Southeast Asia. We love outdoor adventures, tasting local specialties, and island hopping through tropical destinations. Hopefully, our guides and authentic experiences will inspire you on your own travels!
