In case you missed it, we’re about to travel to Italy for an intergenerational trip to celebrate my big 40th birthday later this year and my mom’s 70th birthday! When planning my outfits for this trip, my biggest inspiration was definitely the fact that I’m traveling with my parents. I tend to be a pretty conservative dresser anyway, but knowing this is a family trip made it even easier to lean into that. Even when helping my daughter Greta choose her looks, I found myself saying, “You can’t wear that, we’re with my parents!”
My focus for this trip is comfortable and classic pieces that are in my somewhat-neutral color palette. My sister Andi went to Italy years ago and mentioned feeling out of place in super bright colors, so I’m keeping that in mind. We’ll see if my thoughts change once I’m there!
Dress | Jacket | Bag | Sandals | Shop The Playroom Hallway
At home, my style is much more casual – think jeans and a t-shirt. For this trip, I’m definitely elevating my outfits. Somewhat surprisingly for me, I don’t have a single pair of blue jeans in my bag right now! I’ve heard a lot of people say “You don’t want to look too American.” I guess people mean “too loud” when they say that, but we are American, and we don’t only dress one type of way? I also wouldn’t expect an Italian to have to dress “American”—whatever that means—when they come to the States. :)
Normally, I pack by category (all dresses in one cube, all tops in another, etc.). However, for this trip, I’m planning to pack more by complete outfits. I’m trying everything on beforehand to avoid bringing anything unnecessary. I’m also very open to buying new pieces while I’m there—that’s part of the fun of travel. A vintage-style printed scarf? An Italian linen top? A Florentine leather bag? I can’t wait to see what inspires me.
We’ll be checking our bags, and we have direct transport to our resort, which makes the travel more seamless. This isn’t a backpacking adventure, so I don’t have to pack too light, thank goodness. I’m sure when I get back, I’ll have plenty of insights on what worked perfectly and what I might do differently next time!
The Outfits I’m Packing for Italy
Sweater Vest | Jeans | Sandals
I feel like a tone-on-tone white look feels very fresh and European for summer. The sweater vest is from Walmart!
T-Shirt | Scarf | Pants | Sandals
These Rhone pants are normally outside of my color wheel, but I lovvvvvve them so much. Butter yellow is still having its heyday!
Gingham Shirt | Shorts | Flats
This look is an homage to my mom! A crinkle black & white check button-down is so light, it feels like it’s not touching me at all. Just got these trouser shorts from American Eagle. Size down!
These pants are funnnn. Pairing them with my lightest-weight black tee. Just imagine all of this with sunglasses, k?!
Have had this dress for a couple months (in black too!) and it’s just the best. I just got the red Adidas Mary Janes for the trip, and I’m so happy with them. They’re true to size!
Scarf | T-Shirt (similar) | Linen Pants | Flats
So glad I got these Athleta linen pants in two colors. They are so comfy and lightweight. Trying out the silk scarf on my head—it just feels right!
You have to have a dress-up outfit for a nice dinner out. This one is as comfortable as can be, but also feels Roman Holiday to me.
I couldn’t decide at first if this was giving night out in Florence or bathrobe and room service, but I think I’ll give it a go.
I surprised myself a little by going for this chartreuse swimsuit for poolside, but it feels like a fun choice for travel abroad. Pairing color-on-color in an unexpected way with this cover-up!
Swimsuit | Wrap Skirt | Sandals
If you thought this was a dress, look again! It’s a swimsuit and wrap skirt with the perfect vintage-style botanical print. I can’t get enough of this beautiful milk chocolate color.
What Chris Is Packing for Italy
Chris had to get in the action too! Somehow he packed his bag in one hour though. For reference in these photos, Chris is 6’4″ tall and a size large in tops, size 34 W x 32 L in pants.
Shirt | Sneakers (similar) | Pants
Coming out of the gate strong with this look. Are we strolling through the Boboli Gardens in Florence? I think we are.
Shirt | Linen Pants | Mesh Sneakers
The white embroidered floral on this shirt feels like it’s taken from some antique Italian tapestry. The shoes look so Euro and have a cult following—the best part is that they’re slip-ons.
A classic look for a classic guy. The shoes here are the star of the show—they’re Oxford shoes, but they’re NOT. They have the most comfortable sole. A travel hack for walking to a nicer dinner out on cobblestone streets!
When I shared this look, I knew it was coming. The scores of DMs that “Italians don’t wear shorts!” Welllll, we’re not Italian. The temperature in Rome is in the 90s this week. And I’ve scoured online to find that in fact, for sightseeing and informal osterias or trattorias, shorts are fine. These feel like they could have been in style for eras, with that sun-washed color.
Linen Blazer | Pants | Tee | Sneakers
I think of this look as a slightly more elevated street style for a long walking tour where we might retreat into a beautiful church with frescoes. The light colors are perfect for summer.
This is Chris’s absolute favorite shirt. so of course it’s getting packed. Unlike all the linen, this shirt is wrinkle-resistant so if he wants to look a little more “buttoned-up,” he can wear this with shorts or pants.
Shirt | Pants | Sneakers (similar)
Gonna need a fedora and sunglasses with this outfit. This look is very breakfast-lounge-at-the-villa style, and I’m here for it.
This would be great for a night out in Tuscany. It’s giving “casual George Clooney” to me. And those SHOES!
Polo Shirt | Pants | Sneakers
Is this my favorite look on him? It might be. This blue-and-gray combo feels old-world Italian in the best way.
Shirt | Shorts | Mesh Sneakers
I’m no expert, but it seems like the European summer uniform has to be linen. This dusty green color is subtle and so luxe.
Tank | Swim Trunks | Mesh Sneakers
And one more for pool day at the resort! The girls will probably be most excited about swimming (their favorite thing about travel anywhere), and I know we’ll want to take a dip to refresh ourselves between the travel and excursions.
I collected all of our outfits for travel abroad on our LTK so you can save your favorite looks easily! I included the girls’ outfits as well, since I told them that Lilo & Stitch-themed tees were off limits. (See?? I’m trying to keep us elevated!)
Hi! I can’t find the link to the white, slightly sloughy purse Julia took to Italy. Please and Thanks!
I’ve got you! It’s from Mercules here.
Just want to ofer some personal thoughts on the decades long discussion about “looking American” when traveling abroad. The core beef the rest of the world has with “American” dressing is that generally we are too casual for their cultural norms. Most cultures see dressing up as a form of respect and informal dressing as disrespectful, especially when touring churches, memorials or other places of cultural pride. Formal dressing is often more subdued in palette, but color is absolutely embraced as long as it isn’t too informal or gives celebratory/party vibes out of context. Tennis shoes can be neat, clean and part of an overall smart look, or they can be the last straw on an outfit designed for working out or lounging. We aren’t really that different in how we view people’s clothing choices, even if we are more used to public recreational events including hordes of people dressed like they might go home and mow the lawn. Some Americans are used to Sunday/church dressing expectations, which might even go up a notch for major holidays or weddings. All cultures do this, it’s just our bar for daily dressing is less formal. But, having recently traveled to Europe after a long absence, I can tell you that even Europeans are getting more casual, especially under 50 years old. They might opt for “smart” versions of tennis shoes or denim more often but they wear them just like we do. Also I think it is important to know if you are dressing to meet specific Europeans (like for business, or a hosting family, or some other social context) or if you are dressing for just public space appropriateness. The former might require more strategy – just as going to a family wedding or clarge ompany picnic requires more thought. Anyway, posting this hoping its steers away from cultural defensiveness about being American and being judged and toward a better understanding that some effort of formality and attentiveness to ones appearance is really the only ask. And of course, not even all europeans rise to the “anti-American” standard we’ve heard so often – mostly from people trying to sell you things. So in all, I think you are doing exactly right – taking time to think about who you are with, what you want to communicate and how to be comfortable. Have a wonderful time.
Love all the looks, including Chris’. If you don’t want the striped dress to look robe-y, you can consider swapping out the belt that came with it for a tan or even raffia one. It’s still cute either way.
Have fun and soak up all the sun!!
Check out Rick Steve’s website for dressing in Europe.
Love the looks! Just got back from 2 weeks in Umbria, Tuscany, Florence, Rome, and Ischia and will say that it’s HOT out. You will definitely want shorts and you won’t think twice about wearing them, promise!! Highly suggest Oltrarno in Florence – the paper goods at this shop are incredible: legatoriailtorchio.com