I'm Going to Tuscany for 2 Weeks—Here's Everything in My Cart Right Now

Harsh truth coming at you… Fashion people have many wonderful attributes—e.g., the ability to adopt "risky" trends, discover rising brands, and curate capsule wardrobes—but packing pragmatically for a vacation is not one of them. Even the most devout minimalists can find that it's easy to transform into a maximalist once it comes time to crack open the suitcase. After all, who hasn't overpacked before? Ahem, guilty as charged. It's a common travel mistake, but it's one that I'm personally hoping to avoid as I prepare to travel in the coming days. If you clicked on this article, I'm guessing you, too, are planning a trip to Tuscany, Italy. Whether you'll be exploring Florence or heading to the Chianti countryside, chances are you're stressed about choosing what to wear while you're there.

Luckily, you're not alone, as I've been grappling with choosing what to pack for a trip in the region for almost two weeks during the fall. In an effort to serve my self-interest and hopefully help you, I did extensive research to identify the best items to pack for a long trip to Tuscany. Taking into account the region's climate, cultural dressing norms, and wearability, I was able to narrow down the packing list to 20 items that are worth the luggage space. Plus, I shopped out each of the key items from contemporary and luxury brands to ensure you look like a local who owns their very own villa in the countryside. Note: You don't have to pack every single item included, but this list is a great starting point for deciding what to pack and even what to purchase for a trip to Tuscany. Buon Viaggio!

Let's be honest. It's commonplace for fantasies around Tuscany to include the perfect weather where the landscape's rolling hills are covered in the sun. But like most destinations, the temperatures do shift in the fall from warm to moderate. (Average temperatures range from 50 to 72°F.) With that in mind, it's essential to pack layering items that can be styled in various ways, like a well-tailored blazer. Packing this jacket will ensure you're not cold while also making you look impossibly chic. 

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It's typically best practice when traveling to avoid taking your most expensive jewelry on the trip with you for safety reasons. But that doesn't mean you should skimp out on the bling at all. Instead, pack at least one pair of sculptural earrings that allow you to add a little shine to your travel ensembles without going overboard. 

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Just because you're going on vacation doesn't mean you should leave all your beloved staples behind! One of the benefits of bringing a button-down shirt with you is that it can be worn without having any wardrobe mishaps as you make your way around Florence. It's versatile enough to be worn in different ways to various destinations.

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Another staple you should seriously consider taking with you? A simple tank top. While this item may feel a bit too casual to the point where one might catch side glances from the locals, there is a way to make it work. First, invest in a tank made from luxurious materials or with an interesting neckline to elevate this item. Secondly, err on the side of formality when styling this item by wearing it as an underpinning underneath your blazer or button-down throughout the trip. 

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Typically, it's custom to dress up more when traveling to Italy versus when you're within the United States. So you'll want to avoid packing casual items (sorry, leggings) and choose bottoms that are more polished, such as wide-leg trousers. The benefit of packing these pants is that you won't stick out like a tourist while you're traveling. Plus, the silhouette is breezy enough to allow you to chow down on pizza and gelato.

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With ballet flats still trending, there's no better shoe style to pack if you're trying to plan pragmatically. These shoes will allow you to easily roam around cobblestone streets, all while looking impossibly chic. You can't go wrong with bringing any version of this style, but it's worth packing a pair that comes in a neutral hue to ensure they can be worn with different outfits across the duration of your holiday. 

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It may not be summertime in Italy, but that doesn't mean you should be caught without a pair of shades. Packing sunglasses will ensure you protect your eyes on sunny days and make sure you look stylish in all your travel photos. Just be sure to opt for frames with a classic shape so you can wear them throughout the trip. 

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For the evenings when you want to go out, you'll want to have an evening-forward dress on hand. However, this item does not have to be overly formal, as you want it to be a more elevated take on going out. Opt for a dress with appliqués, a pretty material, or a dramatic silhouette to ensure it feels special enough for an evening in Florence. 

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Although the weather is moderate in the fall, if you happen to get cold easily, you should consider packing a pair of sheer tights for the trip. They're something you can style underneath your dresses or shorter bottoms for the evening or even underneath pants if a cold front comes into town last-minute. 

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None of us want to hear "attenzione, pickpocket" as we travel, so choosing the right bag to wear while traveling in Italy is paramount. Typically, you don't want to wear anything that can be easily accessed from behind (e.g., putting your wallet in your pocket or wearing a backpack), and you should avoid anything that's easy to grab out of your hands quickly, like a clutch or mini bag. Instead, consider packing a shoulder or crossbody bag that allows you to carry your items firmly underneath your arm. 

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As mentioned before, Tuscany's fall weather is quite mild, so it's worth bringing a coat with you in case there's a day that's a bit chillier. Rather than packing it, I recommend wearing it on the plane to avoid it taking up too much space in your suitcase. You'll want to wear a neutral coat, as it will allow you to easily pair it with different looks during your time away. 

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Another cold-weather item you should consider packing for a trip to Tuscany? A minimal sweater. While you don't have to pack a chunky cable-knit for the climate, it won't hurt to have at least one lightweight sweater-vest, cardigan, or thin crew-neck knit with you. 

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It would not be a roundup of the best things to pack for a trip to Italy without at least mentioning maxi skirts. In some ways, this skirt style has become synonymous with this travel destination—for a good reason! It's the perfect item to wear while exploring the city, grabbing a glass of wine, or basking in the Tuscan sun. Even in colder months, you can get away with wearing this item if you pay attention to the materials and styling. 

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While you're rightly justified in worrying about packing a pair of shoes that make exploring the city not painful, it's still worth packing at least one pair of more "formal" shoes if you have reservations at the buzziest restaurant or tickets to the opera. I recommend opting for pointed pumps in a neutral hue that either have a kitten heel or wedge for comfort. 

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When it comes to packing, there's only one general guideline I abide by—the three-way rule. Basically, this guideline requires that anything you pack should be able to be worn three different ways in case you have to rewear something because of the length of your trip or if you lose your checked-in luggage. One piece that can meet this requirement? A pretty top. The benefit of packing a more dramatic top is that it can spice up those "simple" staples you've packed, like trousers, jeans, and maxi skirts. 

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While wearing a belt in the TSA check-in line may be a general no-no, wearing it while you're exploring your destination is a whole other story. For those packing staples like trousers and jeans, you'll want a small accessory that makes them feel a bit more elevated—enter the embellished belt. Choosing a belt with bolder hardware will allow your staples to shine. 

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It's time to be real. Not all denim is worth packing for a trip to Europe. Since fashion in Florence errs more on the formal side, some types of jeans will have you sticking out like a sore thumb. But one style that does work is relaxed wide-leg denim, as they give off the feel of trousers, so they feel a bit more formal. Just be sure to pair them with polished separates to elevate them even further. 

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Another item that can be controversial to take on a trip to Europe? Sneakers. While this footwear is undoubtedly essential, it's common knowledge that many locals associate it with Americans negatively. But I believe it's because of two factors: wearing running sneakers over lifestyle ones while traveling. The second factor comes down to styling. There's nothing wrong with wearing a pair of sneakers. You'll want to balance out how casual they are by wearing them with elevated separates. 

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Although we're well past the summertime, I can't possibly think of a more quintessential item to pack for a trip to Tuscany. Packing a dramatic white dress will allow you to indulge in the fantasy of serving up a full look while frolicking in the vineyards. On a more pragmatic level, it's the type of item that you can wear from day to night without having to return to your accommodations. 

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Lastly, I'd be remiss if I didn't mention the importance of one last thing: your travel luggage. While I've hopefully been able to give you a great starting point of what to pack for your trip to Tuscany, you can't go anywhere without having somewhere to put all your things! Therefore, it's essential to have bags that you can trust to outlast the wear and tear of the check-in process and ones that are pragmatic carry-ons too. If you're traveling for an extended period of time (like me), there's nothing better you can buy for this trip. 

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