What to Wear in Italy

Helping you fit in with the stylish Italians with these handy tips! You'll learn how to pack for Italy and how to put it all together once you're there!

Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will make a commission, at no extra charge to you. I received free product from Wool&. As an Amazon Associate, I earn from qualifying purchases. Updated April, 2020.

Wondering what to wear in Italy?

Of course, in addition to all the history, there's also the lovely culture of relaxed living, fine wines, delicious pastas, and chic people.

Even if you've never yet been to Italy, we all know that that Italians are known for their fashion sense. And, we know, tourists are...known for exactly the opposite. 

​Italy is one of the greatest tourist destinations in the world because of its incredible collection of historic sights, dating back thousands of years to the Roman Empire (and beyond). 

There's no reason that you can't find a happy medium and feel comfortable for touring, while simultaneously looking and feeling stylish in one of the most fashionable cities in the world.

So let's talk about some items you'll want to pack for your trip to Italy! My what-to-wear-in-any-city philosophy is always to tell you about my experience, what I wore, and what I'd recommend, and to suggest some options that worked for me/ may work for you. While there are tons of links to products and suggestions, of course assuming you have these items in your wardrobe, throw them into the bag and there's no need to buy anything new!

Start with packing cubes

I am all about packing cubes. They keep you organized before, during, and after the trip, and they're affordable! They're also a great way to store souvenirs for your trip home.

Check-out my Europe Travel Essentials - the constantly updated list of all the items that I can't travel without!

What to Wear in Italy:
​Finding the Right Shoes

For me, there are several types of "essential" shoes for Italy: loafers, boots, and heels.

​For day-to-day touring, I love loafers, which, in addition to being comfortable, trendy, and classic, keep my feet clean and protected during lots of walking. For evening, I like some wedges. 

For colder months, I like boots and booties from Blondo. They come in *waterproof* options and are super comfy. In warmer months, I'd bring a pair of sandals for giving your feet a break and helping you cool off.  Avoid plastic "beach flip flops."

The age-old advice for tourists has always been not to wear "clunky, white tennis shoes," because they make you look like a tourist. Ironically, "kids these days" are rocking some seriously giant white tennis shoes as a fashion statement. That said, the shoes you wear to literally play sports are still not cool . If you must wear tennis shoes, then go full Emma Thompson in Late Night and rock those teenager tennis shoes and make them your own! Or, get some tiny Keds.

Piazza Navona, Rome

What to Wear in Italy:
​A Small Purse is a Good Purse

Piazza Madonna dei Monti

​There are a few things to remember when selecting a bag for your trip to Italy. First, I'd bring more than one. I like to have a more practical bag during the day, and a nicer bag for evening outings or special events.

Additionally, in touristy areas, beware of pickpockets. I highly recommend a purse that zips and/or closes fully, and cannot be easily opened without you noticing. 

I like a small bag. It's easier to carry, and will deter you from bringing too many possessions. Remember that some museums will make you check large bags. It sometimes costs money, separates you from the items you wanted so badly, and slows down your trip. 
I'd recommend a simple Leather cross-body (this one is made of Florentine leather).

I also bring a nicer purse for dinners/shopping. I don't carrying it all day, but it's good to have, especially if you'll be going to some higher-end places during your stay. How about a classic straw bag?

What to Wear in Italy: Skirts and Dresses

The Pantheon at night

If you're dreaming of Italian romance a la Roman Holiday, skirts and dresses should be in that suitcase! Many of the dresses I'm wearing in the pictures in this blog post are actually from TJ Maxx! I'd also recommend Wool& for sustainable, washable, lightweight wool in cooler months!

Be mindful of religious dictates at the Vatican and some churches.For example, per The Vatican website: "Entry to the Vatican Museums, the Sistine Chapel, St. Peter's Basilica and the Vatican Gardens is permitted only to appropriately dressed visitors. Low cut or sleeveless clothing, shorts, miniskirts and hats are not allowed."

​Of course, you'll also likely want to pop into random churches that you happen upon on your travels, so be sure to keep this in mind when packing skirts and shorts.

And if these piazzas have you dreaming of sipping an apertivo, while overlooking the Pantheon at night, check out Rome's Best Piazzas. ​

What to Wear in Italy: Lightweight tops

Regardless of season, it just doesn't get terribly cold in Italy - and the sun is often quite warm. Particularly in fall, it might be warmer in Italy than you're expecting! So, I like to stick to lightweight shirts, and then to carry around that light jacket, in the unlikely even that you get cold! I've recently discovered Canadian designer KOTN, which has a wide selection of reasonably priced, lightweight shirts.

What to Wear in Italy: Pants & Shorts

In the peak summer months, when the average high temperature in Italy is 86, the sun is hot, and the crowds seem to be multiplying, at least a couple pairs are going to be a necessity. JCrew Factory has incredible deals on shorts. J McLaughlin has some great longer options.

For shoulder season and winter, I'm all about those light-weight pants. Particularly crepe pants from Eileen Fisher.

What to Wear in Italy:
​Feel Fancy in a Wrap

Exploring Rome

I absolutely swear by a great wrap.
​Wraps are perfect for the plane, they can be good to have around if someone is underdressed for a religious site, and, most importantly, they'll make you feel super fancy!

What to Wear in Italy:
​A Bit of Pizzaz with a Scarf

I remember getting to our hotel, after that long, Transatlantic flight, getting to the hotel (our room wasn't ready), and going to wander around, sweaty, waiting 'til we could get into the room and take a shower. The first thing I thought when I got back and started getting dressed after that adventure was..."I need to spice up the outfits I brought."

Thankfully, I had brought a TON of scarves, and next thing you know, I am fully-scarfed! A few of my favorite scarf finding locations: Nordstrom Rack, Tuckernuck, J McLaughlin, and Goodnight Macaroon, depending on season!

What to Wear in Italy: Should I Bring a Hat?

Whether you'll want to bring a hat will strongly depend on the time of year you're visiting. In Spring/Fall it's likely not necessary, but in the Summer, it's always nice to keep the sun off your face! For long, outdoor activities, such as exploring The Roman Forum or Ostia Antica, a hat can definitely help prevent tourism fatigue.

Planning a trip to Italy? Check out my Top 10 Tourist Mistakes in Italy - and how you can avoid them!

What to Wear in Italy: Top it off with a Blazer

Obviously it'll depend on the time of year, but wow can people in Italy rock a blazer (gents and ladies). This is a bit more of a "deep cut" as most people don't tend to think of blazers when they're packing for a touristy vacation, but I thought I'd throw it in here, just so you have the full scoop! I'm all about Boden lately - and they're available in a bunch of colors to suit any wardrobe!

Love ancient history? Check out these Roman coin-inspired earrings from J. Bubs!

Thanks so much for stopping by!

I hope you have the most fabulous trip to Italy - don't forget to leave your outfit recommendations in the comments!

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