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What to Wear: Easy & Chic Italy Vacation Outfit Ideas

If you are looking for outfit inspiration for your next vacation to beautiful Italy, you’re in the right place! Italy is one of my most favorite countries to visit – be it for the delicious carbonara (yum! my absolute fave), beautiful museums, rich culture and history, breathtaking scenery, and beyond.

I also find packing for Italy vacation outfits a lot more fun because the locals aren’t shy about dressing up and looking good. With that in mind, don’t be afraid to step outside your comfort zone and wear what you really want to wear – after all, you’re on vacation! Definitely pack daytime outfits for when you’re out and about exploring museums and enjoying gelatos, but also make sure to mix in some fun and maybe a little fancier outfits for a glam night out on the town!

And if you’re still on the hunt for the perfect walking shoes that are cute AND comfortable, check out my Top Travel Shoes Picks (tried and tested on the cobblestone streets of Italy!).


I consider myself a little bit of an overpacker, but I’ve gotten a lot better at packing more efficiently over the years, especially if I’m trying to save some suitcase space for souvenirs and goodies (hello beautiful VAT Refund! 🤩). And it is all thanks to the exact steps below!

  • Visualize the outfit aesthetic I am trying to achieve, especially against the scenery of the places I am visiting
  • Pick individual wardrobe pieces that I intend to wear on my trip (including accessories like handbags, hair pieces, sunglasses, jewelry, shoes etc)
  • Identify core wardrobe pieces that can be reworn in different outfits
  • Mix and match individual pieces to build entire outfits along with accessories (this is the fun part!)
  • Take pictures of myself in the mirror while wearing each completed outfit
  • Create stickers from each completed outfit photo
  • Paste each sticker into iPhone notes to create my own little organized outfit book

Even if you’re packing light, bringing all the right items with you can help you maximize your vacation trip so you can truly leave your worries behind and live in the moment! Pack like a pro with my Travel Essentials For Europe: The Ultimate Game Changers!


As I’m finalizing my travel wardrobe, a few questions I like to ask myself are:

  • Will I actually wear this if I packed it in my suitcase?
  • Do I really need this? Or can I re-wear another piece to achieve the same look?
  • What is the weather going to be like? Are there any clothing rules that need to be respected? (eg. in Italy many churches, cathedrals, and museums require at least your shoulders to be covered so a linen scarf or shirt will come in handy)
  • Do all of my outfits look the same? If so, I’ll swap some out for a color pop here and another texture piece there to create variety
  • Did I pack some clothes with a little extra breathing room to accommodate my vacation appetite (lol) 😅
  • Do my accessories (like shoes and bags) transition well from daytime to nighttime?


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Now it’s onto the packing part! While I’m on a limited travel wardrobe, I tend to keep my color scheme nice and neutral for my core pieces. Going back to basics on the key outfit pieces makes it so much easier to mix and match individual items to build an entire outfit. However, I always make room for a few fun prints or statement pieces that really make me feel like I’m on vacation.

Scroll down for cute and easy outfit ideas for your vacation to Italy!


PRO TIP: 2-piece linen sets are a great way to create different outfit options. Wear them as a matching set, or style the top and bottoms individually with other pieces in your travel wardrobe. If you’re packing light, this is my secret weapon for refreshing clothes to re-wear without feeling icky! Bonus points: It works well with my sensitive skin AND removes wrinkles too!!


PRO TIP: For tops with tricky necklines where you want to hide your bra straps, wear seamless and lightweight adhesive nipple pasties like this one (my personal fave and closet staple), or this one for more lift!



PRO TIP: In Italy, many churches, cathedrals, and museums require at least your shoulders to be covered so a linen scarf or shirt will come in handy!





PRO TIP: Wearing the right travel shoes can make or break your vacation. Make sure to get walking shoes that are comfortable for all-day walking in Italy yet cute and stylish to match all your outfits! This pair is my personal fave that I wear on ALL my vacation trips.

For new sneakers, I like to break mine in by filling up ziplock bags of water, inserting them into the front of the shoes, then putting them in the freezer overnight to help stretch out the toebox.

For new Birkenstock sandals, before packing them on any vacation trips, I wear them daily for at least a month (the longer the better!) so the footbed can mold to my feet.

I hope this packing guide for Italy vacation outfits was useful in helping you craft your own travel wardrobe for your trip!

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