Style Guide: How to Dress When You Travel Italy
You know the saying about “when in Rome”? It really does make a difference, and this is especially true when it comes to fashion and how to dress while you’re visiting the magical country of Italy. Not necessarily because you want to compete with the style-conscious, Gucci-loving Italians, but because what you wear can make a huge difference in how much you enjoy your trip. I fell in love with Italy in 2012, and have gone back every year since (minus the lockdown years), and every time I learn something new about how to pack, what to leave at home, how to dress (or not) and what to do differently next time.
Like any culture or destination, there are some definite do’s and don’ts when it comes to what (or what not) to wear while in Italy. If you’re planning a trip to the boot-shaped country, here’s a quick guide to help you pack wisely and for a trip you’ll enjoy from start to finish.
Wear comfortable shoes. Cobblestone streets are common in most cities, including Rome and Florence. The ancient city of Pompeii is downright difficult to navigate (but worth every second). Unless you’re somehow adept at navigating uneven terrain in high heels, opt for low-heeled (I’d go with flats), comfortable shoes or boots (if winter). Italians are generally a stylish bunch, however, so if it were up to me, I’d leave the bright white Reeboks at home and go with a stylish black loafer, tall brown boots, or comfy flats you can walk a few miles in without getting blisters. Pro tip: If you’re going to Florence, oh baby—the leather! Save some money to splurge on a high-quality pair of leather shoes or boots that’ll cost you far less there than the same pair would in the states.
Take note: Comfortable doesn’t include flip flips or athletic shoes—save those for the beaches and gym. Italians frown on too-casual footwear in the main cities, and maybe it doesn’t matter to you, but I don’t love to stick out as a tourist. One time I was walking around the streets of Rome in what I thought were adorable flip flops . . . until I noticed that way too many people were glancing at my feet and chuckling. I stopped to consult Google about that, and that’s when I learned that Italians truly don’t consider flip flops appropriate city footwear. They’re good for the beach or pool, but otherwise, wear a real shoe.
Pay attention to the weather. Summers can be steamy, but shorts are still regarded as resort wear by most Italians. Opt for casual skirts, dresses and capris instead. If you plan to visit any of the thousands of churches throughout the country, you’ll need to be sure your shoulders and knees are covered before you enter, even in the summer. A scarf you can throw around the shoulders will suffice when the temps are too warm for long sleeves. Take note: Italians rarely show bare arms or legs until June or July. In the winter, temps can get chilly, especially in the North, but even in Rome. If you’re traveling from Venice to Florence to Rome (very common), you’ll notice a difference in climate to some degree. Plan for layers! I don’t lug around a big winter coat (you’ll typically won’t need one, unless you’re going to the mountains), but I do dress in layers and pack one medium-weight coat for the chilliest days, along with a few scarves I can interchange. Plus, a wool beanie is both cute and practical.
Tip: A small raincoat or travel umbrella is a smart accessory to have year-round.
Don’t forget accessories. A hat and sunglasses are smart to have year-round, even in the city; piazzas can be hot and bright for a large part of the year. Most Italians favor a few simple pieces of jewelry, and Italian women generally wear simple makeup, so unless you love to really glam up most days, you can get away with a light makeup bag.
Wear bright colors sparingly. This is just a tip if you don’t want to stand out as a tourist; if you don’t care, wear what you love! Italians tend to dress in neutrals or muted colors, especially in Florence and Rome. That doesn’t mean you can’t add a little color with jewelry, scarves, pashminas, or even a tank top layered under a blouse or jacket. Just don’t go overboard or you may find yourself drawing unwanted attention.
Dress for safety. It’s hard not to look like a tourist when you are one, but there are things you can do to minimize attention and still stay safe. This is particularly true if you’re a woman traveling solo through Italy, which is typically the way I prefer to travel when I’m there. Opt to carry a messenger bag or sturdy leather purse rather than a backpack or fanny pack. A cross-body bag with reinforced straps will keep your belonging safe from pickpockets and knife-wielding thieves (not that they want to use the knife on you—they’re more likely trying to cut your purse or bag straps). Keep important documents, money and credit cards in an inside jacket pocket or the front pocket of your pants or jeans, never your back pocket. I’ve run into too many Americans who’ve had their pockets picked, cash and passports stolen from their backpacks (while they were wearing them), and bags grabbed from their hands, usually in train stations or in crowded piazzas where it’s less likely for the thief to get caught. Always be aware, and dress to blend in rather than stand out.
One last tip: Don’t overpack. Try to pack pieces you can interchange and create several outfits from, because let me tell you—lugging an overstuffed, heavy suitcase over cobblestones and up steep stairs or through crowded train stations is a real pain. My plan of attack is to just take clothing in neutral colors, bring layers, create several outfits from a handful of pieces, and add pops of color with accessories (many of which I just buy there).
