10 Fashionable Outfits for Your Italian Vacation

Whether you’ve been dreaming about strolling along the cobblestone streets of historic cities or just looking to savor some seriously delicious gelato, you want to be ready to embark on a stylish journey like never before. To help make sure you’re dressed to dazzle, we’ve come up with a list of 10 fashionable outfits (including comfortable travel shoes for women) for your Italian vacation, along with some of the best Italian cities and sites to wear them in. Let’s dive into new adventures as we say Buongiorno to unparalleled style!

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1. Gingham Midi Dress — Gingham is a popular pattern in both the U.S. and Europe and, according to fashion experts, is usually designed with a checked two-color pattern like red and white or blue and white gingham. Embrace the charm by dolling up in a gingham midi dress as you trek through the Italian countryside. Accentuate your look with a crossbody bag and leather sandals as you take a day trip to Cinque Terre to see the towers. 

2. Denim Dress — For a contemporary look, wear a denim dress and add understated gold jewelry. Add wedges to dress up your look as you visit vineyards in Tuscany. The versatility of a denim dress is perfect for sightseeing in Italy. Thanks to its timeless and iconic appeal, it’s a great choice for anywhere you dine that requires a more fashion-forward look or something more casual that’s great for a laid-back yet modern look.

3. Midi Wrap Dress — For a look with timeless elegance, try a floral or solid-colored midi wrap dress. Pair your wrap dress with espadrille wedges while exploring the charming side streets of Venice or Florence. This well-fitted and flattering dress is easy to style. It’s a major confidence booster that’s suitable for a variety of body types, so you’ll be able to enjoy your Italian vacation experience to the fullest. 

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4. Maxi Dress — Exude effortless glamour with a maxi dress, embellished sandals and statement earrings. It’s the perfect outfit for you to enjoy a romantic dinner on the Amalfi Coast. You’ll make maximum impact in a maxi dress that offers effortless elegance as you look chic and put-together with minimal effort. If you’re visiting religious sites like the Vatican, a maxi dress is considered a modest and respectful option since a more conservative dress code is expected.

5. Striped Shirt Dress — For a cool and casual look, wear a fashionable striped shirt dress with white fashion sneakers. You can give your dress more of a silhouette by cinching it with a belt. You’re sure to rock the streets of Naples when you finish your look with oversized sunnies. It’s a comfortable and breathable option, so you’ll stay nice and cool as you explore landmarks and picturesque streets. Striped patterns are worn by both locals and tourists in Italy, so you won’t stand out when you’re wearing a striped shirt dress.

6. Flowy Skirt and Tank Top — If you enjoy a bohemian vibe, wear a flowy maxi skirt with a tank top. Add to the laid-back vibe of this look by pairing comfortable sandals with your flowy skirt and tank top. You’ll fit right in with the artsy vibe in Siena when you complete your outfit with a woven tote bag.

7. Sleeveless Linen Top and Linen Pants — When the Italian sun is shining down on you, you’ll want to stay cool and chic in a sleeveless linen top with breathable linen pants. Wear it with dainty jewelry and comfortable sandals as you explore the historic sites of Pompeii.

8. Off-the-Shoulder Top with Gaucho Pants — For a sweet and flirty look, try a solid-colored off-the-shoulder top with patterned gaucho pants. Add height to your gaucho pants with closed toe shoes. When you’re doing a day of sightseeing in Rome, protect your eyes and face with a wide-brimmed hat and sunglasses.

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9. Floral Pants and a Pastel-Colored Top — Make a fashion statement with floral pants and wedge sandals that are comfortable and chic. Add a pastel-colored top as a breezy addition to this outfit. Stroll through the wineries of Chianti with a glass of chianti in your hand. This fashionable and trendy pairing matches the Italian appreciation of fashion and design.

10. Tailored Jumpsuit — While many of the outfits we previously listed can be dressed up for an evening look or dressed down for something more casual, the tailored jumpsuit is the perfect sophisticated evening outfit. Pair your jumpsuit with block heels and an embellished clutch to elevate your style during a night out in the buzzing city of Milan.

Now that you know what to wear for your fabulous Italian vacay, say arrivederci to your old wardrobe. Get ready to embark on your Italian escape! These comfy shoes and fashionable outfits are perfect for walking through the timelessness of Rome’s cobblestone streets, taking in the vibrant colors of the Amalfi Coast and, most importantly, getting you through airport security.