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!

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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). 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, of course, tourists are...let's just say: known for exactly the opposite. But, of course 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!! 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!

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Packing for Italy: Start with Packing cubes

Before we get to the clothes, for those of you who've read my other packing lists, you'll know that I am all about those packing cubes. Literally can't get enough of them

These little cubes keep everything you pack organized before, during, and after the trip, and - the best part- they're super affordable! I love being able to keep small items neat and tidy *in* the hotel room, and they're also a great way to pack up souvenirs for your trip home.

And, if you're concerned about hotel room germs, you could even leave all of your items in the cubes and just transfer them into the drawers in your hotel. We just bought my mother-in-law a set for her birthday!

For even more travel essentials, check-out the constantly updated list of all the items that I can't travel without!

Packing for Italy: Finding the Right Shoes

For me, there are three types of "essential" shoes for Italy: loafers, heels, and boots or booties. For day-to-day touring, I am all about these Sam Edelman Loafers, which are comfortable, but also keep my feet clean during lots of walking. For colder months (though I wear them in spring and fall as well), I like Blondo booties. They're *waterproof* and super comfy. For evening, I like some low block heels, for as long as they're in style! (I add this as a disclaimer just because they seem so 90's to me that it's hard to believe they're back!! Get me my Spice Girls album!) These recommendations are also below this paragraph, so you can see some pictures.

​And, if you're traveling in warmer months, I'd bring a pair of sandals for giving your feet a break and helping you cool off! Avoid "beach flip flops," but you'll be fine in actual "sandals," though definitely be careful with planning to wear them long distances, unless you know they are *extremely* comfortable.

Ironically, the age-old advice for tourists was always not to wear "big, clunky, white tennis shoes," because they make you look like an American. Ironically, "kids these days" are rocking some seriously giant white tennis shoes as a fashion statement, which makes me feel super old. That said, the shoes you wear to literally play tennis are still not cool - don't wear those to tour around Italy. If you simply must wear tennis shoes, then go full Emma Thompson in Late Night and rock those giant teenager tennis shoes and make them your own! Or, get some tiny Keds.

Packing for Italy: A Small Purse is a Good Purse

So there are a few things to remember when selecting a bag for your trip to Italy. First, I'd say 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, you must remember that in touristy areas, particularly in Rome, you need to beware of pickpockets. I would highly recommend a purse that zips and/or closes fully, and cannot be easily opened without you noticing. I'm not saying to be paranoid; just be conscious.

And, it's time for my daily reminder: don't talk to strangers who come up to you in public places. They may try to distract you with weird questions like "Are you American?" or "Do you like animal rights?" Just keep walking. It's a ploy so that their accomplice can pick your pocket or reach into your bag. JUST KEEP WALKING.

Back to purses, I like a small bag, as naturally it's easier to carry around, and it will deter you from bringing too many possessions with you. There's truly very little that most of us need to carry around with us on a daily basis. I'd encourage you to carry around as little as possible.

​Also, remember that some museums will make you check large bags. This is a giant pain, sometimes costs money, separates you from the items you wanted to carry around, and slows down your trip if you're having to do this throughout your journey. Obviously I know sometimes it can't be avoided, but if you can, why not!

OK, so actual recommendations! For summer in Italy, I love a straw bag. Trendy, pretty, light, and dreamy - it'll even look good in your pictures! Just don't forget that closing mechanism (this one has a snap).

And for non-summer, and because it's Italy, I also like a simple, Leather cross-body bag. This one is actually made of Florentine leather - why not get into gorgeous Italian products before you even head over!?

In addition to my tiny purse for day time, I also light to bring a high-end purse for dinners/ shopping. I don't like carrying these around all day, but it's nice to have, especially if you'll be going to some nicer places during your stay.

Packing for Italy: Don't Forget the Skirts and Dresses!

If you're dreaming of Italian romance a la Roman Holiday, skirts and dresses should definitely be in that bag! I mostly keep them for evening, but if you're feeling fancy, there's no reason that you can rock them during the day! All the dresses I'm wearing in the pictures in this blog post are actually from TJ Maxx!

Be mindful of religious dictates at the Vatican and some churches.

For example, 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 piazza pictures have you dreaming of sipping an apertivo, while overlooking the Pantheon at night, check out Rome's Best Piazzas. 

Packing for 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.

Packing for Italy: Lightweight Pants (or Shorts)

I'm not much of a shorts girl myself, but 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.

I tend to opt for light-weight pants, largely because I don't like the feel of the back of my legs touching things in public when I sit down? Is that weird? Maybe. Maybe it's just the History Major in me, or the fact I went to school in Colonial Williamsburg. But anyway, I'm all about those light-weight pants. Particularly crepe pants from Eileen Fisher.

Packing for Italy: Feel Fancy in a Wrap

I absolutely swear by a great wrap. They are perfect for the plane, they can be good to have around if you, or someone in your group, is underdressed for a religious site, and, most importantly, they make everyone feel super fancy!

Packing for 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!

Packing for 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 (and, perhaps, your Instagram aesthetic!). 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.

Packing for Italy: Top it off with a Blazer

Obviously it'll depend on the time of year, but boy 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 historic sites 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 I found the most fabulous blazers on there - and they're available in a bunch of colors to suit any wardrobe!

​Check them out here.

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! Also, a little disclaimer - these tips will be helpful across-the-board, but if you're under 18, you'll want to take these tips with a grain of salt and spice things up a bit. I find that most of my readers are similar age to me (mid 20's-40's), but I have had a few, younger, cooler readers confused about my suggestions. If you're a kiddo and you're hipper than me, then let your fashion flag fly!! The Italians are chic, chic, chic, and the younger generation are certainly no exception.

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