Before I get in to all the clothes I packed to spend a month in Italy, can we just appreciate the cleverness of the title for this post and the fact that I crack up laughing every time I read it or think about it?

Alright, now that that’s out of the way, I wanted to share with you one of the biggest struggles in prepping to spend a month in Italy – what to pack! It was so hard to not overpack because my bags had to be under the weight limit and I wanted to bring so many cute outfits, especially since we were spending a whole month abroad.

I did really thorough research online before starting to pack. The biggest thing I wanted to avoid was looking like an American tourist. Not only did I want to blend in with the locals to really immerse myself, but I also wanted to limit my chance of getting pickpocketed. So looking like a local was my goal. I Googled “What to wear in Italy” and scoured Pinterest for the best blog posts. What I gathered from my research was that Italians wear neutrals, they dress up more than Americans for casual wear, they don’t wear shorts, and they dress fairly conservatively. So there went my plans to pack every pair of Lilly Pulitzer shorts I own…

Some of the resources I found that really helped with deciding what to work were, What to Wear: How to Dress in Italy by Miss Adventures Abroad, What to Wear in Italy by The Boho Traveller, and Ultimate Female Travel Packing List for Italy by Her Packing List.

The weather in Italy is so variable in the spring (we went in May) that I also had to pack for 80 degrees or 50 degrees and every temperature in between. We experienced heat, cold, and rain, but luckily what I brought was perfect for all kinds of weather.

I’ll start with my clothes packing list and then show you some of my outfits I wore throughout the month. I’ll link as many pieces I can find still online.

Tops

• Olive tee
• Black crop top
• 2 white tees
• White tank
• Cream peasant top
• Black ¾ sleeve top
• Black and white striped ¾ sleeve top
• Black and white striped tee
• Navy striped ¾ sleeve top
• Pink polka dot top
• Long sleeve olive top
• Blue and white crop top

Bottoms

• Black and white palazzo pants
• Olive jeans
• Black jeans
• Dark wash jeans
• Regular wash jeans
• 2 pairs of cotton leggings
• 1 pair of spandex leggings

 Dresses

• Black and white striped tank dress
• Olive/cream gradient dress
• Light blue striped swing dress
• Navy swing dress
• Olive swing dress
• Vineyard dress
• Blue and white striped dress
• Denim skirt
• Navy and white casual dress

 Rompers

• Blue patterned romper
• Black romper
• Black and white striped playsuit

 Outerwear

• Olive cargo jacket
• Gray duster cardigan
• Denim jacket
• Red sweatshirt jacket

Miscellaneous

• Kate Spade scarf
• 3 ascots
• 3 bathing suits
• White bralette
• Rose bralette
• Crossbody bag
• Large tote bag (for school)

 Shoes

• Black combat boots
• Sneakers
• Jack Rogers (knock-offs)
• Birkenstocks

    

Both of these tops are from Charley’s Boutique. Actually, most of the outfits I brought are. I guess that’s what happens when you work at a clothing store! The first outfit is what I changed into for dinner our first night in Florence with my regular wash Lucky jeans and my Birkenstocks. The weather gets cooler at night in May in Italy so the light long sleeves and jeans were perfect.

The second outfit was what I wore to sightsee around Rome all day. It was really hot in Rome and none of the attractions we went to had any shade. I wore my Birkenstocks since I needed comfy walking shoes. My denim skirt from Altar’d State is one of my favorite pieces in my closet because it’s super comfortable stretchy denim and it’s not too short.

Before I left, multiple friends of mine said, “I can’t wait to see your vineyard pictures!” so I knew I had to find the perfect dress for our wine tour. I searched high and low and finally found this perfect floral maxi from Lulu’s. It was the perfect length so I could wear my flat (knock-off) Jack Rogers sandals with it. I could not have picked a better dress to wear to the vineyards.

   

On our last day in Rome I threw on this mock turtle neck black and white striped swing dress I got from Plato’s Closet in Gainesville. It’s the softest, stretchiest material so it’s so nice to wear all day and the style was perfect for the heat. I wore my Birks with it and was set for the day.

To sightsee around Florence, I wore this navy and white striped top from Forever 21 that I got about 6 years ago and keep as a closet staple. I read Italians wear lots of stripes so I definitely incorporated that into my Italian wardrobe. I paired this top with this little bandana scarf from Madewell. I got this one and a red one before leaving for Italy and now I wear them all the time at home!

    

Following with the stripes trend, I found this gorgeous dress at American Eagle. The material was so light and the colors, pattern, and style were all so perfect for Italy. I wore it walking around Venice with my Birks.

I also wore the blue and white dress (noticing a color scheme?) on the right in Venice. I paired it with a white lace bralette underneath so I would be comfortable all day in the Venice heat. This dress was from Macy’s and the bralette is from Aerie.

    

I broke out the denim skirt again for a day in Positano on the coast of Italy. It was warmer weather on the coast, but a rainy, overcast day. I also wasn’t feeling very well so I went with a simple white tank top from H&M with my skirt.

The outfit on the right was for a day in Sorrento. It was super rainy and cold all day and we were going to be outside walking around the whole time. I always recommend traveling somewhere it might rain with a pair of combat boots. They’re so much cuter than rain boots and they’re waterproof! And if it ends up sunny all day, you don’t look dumb for wearing rain boots. I wore my dark wash Lucky jeans, a white tee from H&M, my olive cargo jacket from Journey’s (linked similar jacket), my trusty pair of combat boots (a favorite of mine to wear in the rain), and a Kate Spade scarf (similar). This jacket was such a good piece to bring because I wore it when it rained or even if it was just chilly in the evening and it paired well with all the neutrals I brought.

    

This black Z Supply romper from Charley’s Boutique is one of the most comfortable pieces of clothing I own. I paired it with my Birks and a Kate Spade silk chili pepper scarf to climb over 900 steps to the top of the Duomo.

When we visited the Colosseum in Rome, I wore a black and white striped playsuit (similar) that hits about mid-calf on me and my Birks (another theme here). It was hot out, but we were headed straight to dinner after so I wanted to be dressed for everything and this was the perfect piece for just that.

    

I brought this athletic outfit for hiking up the top part of Mt. Vesuvius. The top is from PacSun that I’ve had since high school and the spandex leggings are from Nike. I debated even bringing sneakers since my Birks are so comfortable to walk in, but boy am I glad I brought my Nikes. The trail was so dirty and rocky that I needed the coverage and traction my Nike sneakers provided. I also wore a white American Eagle sports bra.

For touring Pompeii, I brought a black crop top (similar) from PacSun and a pair of black and white palazzo pants (similar), both of which I’ve had for about 6 or 7 years. It was hot in Pompeii and these breezy palazzo pants were a good alternative to shorts. Of course, I wore my Birks with this outfit.

    

When we went to Pisa, it was rainy and overcast. I wore my olive jeggings with this cream peasant top (similar), both from American Eagle, with a rose bralette from Aerie. I also wore my denim jacket from Macy’s since it was a little chilly out.

On the flight to Italy, I wore my red bandana scarf with a black and white striped top from Plato’s Closet. I stayed comfy for the flight in my black Victoria’s Secret cotton leggings and Birks.

I brought this Z Supply swing dress (similar) from Charley’s Boutique in both navy and olive. This was one thing I definitely wore multiple times throughout the month. It was so easy to throw on and be comfortable, but also look cute the whole day.

    

Because Italy is surrounded by water, I also brought 3 bathing suits and only ended up wearing 2 of them. The olive one is from Target a few summers ago and the one on the right is from Billabong.

Also, the sunglasses I’m wearing in basically every picture are the pearl/gold My Girl sunglasses from Quay Australia. I also have them in black/blue and they’re my favorite glasses I’ve ever owned.

I ended up wearing all but one top that I brought and I only wore 2 outfits twice. As a bonus, my bags were under weight for the flight to Italy and coming home. So let me be proof that it is possible!! I definitely recommend lots of comfortable sundresses because they’re so easy to throw on, you’ll be comfortable in all kinds of weather, and you’ll look great too. I hope this post helps you decide what clothes to bring when you’re packing for your big Italian adventure!