What to Wear in Italy, From City Style to Seaside Looks

Your flights are booked, hotels reserved, and activities planned for your summer vacation in Italy. Now comes the hardest part—what will you pack? Most Italian holidays include a mix of exploring ancient cities, sipping crisp wine in the countryside, and sunbathing on the rocky coast, so you need to be able to fit a mix of styles into one or two carry-ons that can be easily transported between planes, trains, and automobiles.

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The Midi Dress

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The Linen Trousers

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The Striped Button-Up

Matteau striped cotton-poplin shirt

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Below, find a list of what to wear in Italy this summer and beyond: think breezy linen dresses, easy sandals, and all things raffia. Just add some Italian sunshine and you are ready to live la dolce vita!

City Chic

With direct flights from New York City to Rome, Milan, Venice and Naples, most Italian adventures start in a major city where you can expect to walk at least 20,000 steps per day—meaning it is crucial that you have comfortable sneakers to take you from one tourist attraction to another.

But dressing comfortably doesn’t mean you have to sacrifice style. There are plenty of summer sneaker outfits that will still look chic as you toss a coin over your shoulder at the Trevi Fountain à la Lizzie McGuire, or stroll down the Spanish steps with a gelato in hand. Pair a flowy dress or skirt with colorful sneakers or fisherman sandals, a bag to hold your essentials, and a sweater or light jacket to layer for the cooler mornings and evenings. Andiamo!

Tuscan Countryside

The rolling hills of Tuscany are just a few hours from the popular cities of Rome and Florence, so many visitors head toward wine country to sip on local blends and take in the countryside for a few days. Rent a villa or Airbnb with friends and book a car to take you from vineyard to vineyard for the ultimate under-the-Tuscan-sun experience.

Seaside Style

There is no shortage of beautiful coastal towns in Italy—from the Amalfi Coast and Capri, to Portofino and Puglia, there are hidden beach coves and crystal blue water waiting for you on either side of the ‘boot’. For this part of your trip, you’ll want to pack a mix of swimwear, activewear, and eveningwear so you are prepared for any activity from morning to night. Bring layers for that chilly ocean breeze, and don’t forget to pack your SPF to protect from that strong Mediterranean sun!