Really dressing for Tuscany in general...
When I give you ideas and tips for dressing or packing for Tuscany, I want you to keep a few things in mind:
I always pack everything into a carry-on and personal item. Especially when traveling through Italy or Europe and if you're changing hotels often, lugging around huge checked bags is a hassle. And don't get me started on hauling them through cobblestone streets and up flights of stairs (because not a lot of places have elevators and not many places build living quarters on the ground floor). So because of this, I will keep the amount of shoes I take to about three to four (including the ones I wear on the plane) and I make sure I take clothes that lean towards neutral colors and can make serval outfits out of the same pieces. "Oh the Instagram horror!", I get it, and if your followers have been to Europe, they should get it too.
You need clothes that will transition from day to night. Nothing in Tuscany is close to each other. Your base can be in a small town or bigger city, but other towns like Volterra can be 40 minutes+ away, San Gimignano can be 35+ minutes in the other direction, Siena is one hour and a half, Florence is an hour, so on and so forth. So, on the day your visiting multiple towns you will most probably not be going back to your place of stay to change for dinner (if you're trying to stay in one of those towns for sunset and dinner). This is also the same if you're trying to do a day trip to the coast. If you're visiting vineyards, wine tasting isn't like a typical wine tasting in the states where you get a couple of sips of a couple of different wines and you're done in about an hour and a half after the tour and the tasting. Some might be like that, but if you're booking your tasting with a selection of local cheese and meets or a lunch, you'll be there for at least three to four hours. In the case of visiting Gimonda, you might be there all afternoon. If you're trying to get more then two vineyards in a day, you will probably be stopping to have dinner before calling it a night. So, if you're trying to be cute and practical with you're clothing, you'll need outfits that will be equally acceptable frolicking around under the Tuscan sun and sipping wine at a dinner table.
Because you will most likely be renting a car while traveling through Tuscany, always leave a light jacket in the car during warmer seasons. While it can be 90 degrees+ in the summer, temperatures can drop at night, especially in the towns that have higher elevations.
Flats, block heals and trendy sneakers are the way to go. Do not bother with kitten heels or stilettos. There is cobblestone everywhere and you will tear them up and possibly break an ankle. And while I'm at it, you also won't see many people with sweats, leggings or crocks, it's just not their thing.
So, as you look through the posts, when I suggest outfits, I will suggest pieces that are of all price ranges and can easily be swapped with each other. For instance, a post that features 5 dresses and 5 pairs of shoes means any of those dresses can go with any of the shoes. So this would mean, you can buy three of the dresses from the first post and one of the pairs of shoes and it would all go. A post with 7 tops, 7 bottoms and six pairs of shoes can all be mixed and matched together. In this case, you can buy four tops from the that post with two bottoms and one pair of shoes and it can all go (and it would potentially also make eight outfits). Sometimes you will see some of the same shoes across multiple posts, in that case you might be happy just having one or two pairs that go with everything!
I realize these tips may not be for the social media influencer trying to impress fans with the constant swapping of gorgeous outfits, purses and shoes, but they are for the person trying to make the most out of their trip to Tuscany while still being trendy and practical. So, please read on and I hope my suggestions can inspire you with this in mind.
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