I’m currently working on a new packing list for our 2025 summer trip, and there’s no better way to get started than by revisiting what has worked really well in the past. While I honestly love all of our family trips, I remember being especially happy with what I wore in Italy.
Our Summer 2019 family trip was pretty much a gelato-fueled Italian dream: wandering Rome’s iconic fountains (Trevi, obviously), exploring ancient ruins, and falling head-over-heels for Sicily’s markets, swimming spots (like this one across from our flat in Ortigia), and wildly unnecessary (but 100% worth it) speedboat rides. Sure, it was bananas hot, but still: it’s Italy. I wanted to feel a little bit glamorous and romantic – very much Girl on An Italian Adventure (but the ‘with kids’ edition).
Summer Travel Packing List: What To Wear In Italy
At this point, I’ve got my European summer packing list pretty dialed in. It can basically be summarized in four words: linen dress, tan sandals (haha). But in all seriousness, if you want the general European packing list I use to get started (no matter where in Europe we’re headed), it’s this:
My Packing List For Europe (Summer)
- 4 Dresses
- Jumpsuit or Matching Set
- Pants (or shorts) + Nice Top
- Swimsuit + Cover-up
- 2 Bags (one for day, one for night)
- 3 Pairs of Shoes (flat tan sandals, walkable heels, sneakers)
I use this general list as a starting point, and then choose exact pieces based on the vibe I’m looking for.
For Italy, the vibe is classic prints (like leopard or polka dots), flirty white dresses, vintage-inspired swim, and outfits with a refined sexiness – think old Hollywood glamour, La Dolce Vita. (If you’d like to hear more about how this process works, check out my YouTube video, Packing For Italy: What I Pack For A Summer Vacation In Europe.)
So, based on that general packing list – and the overall vibe I was trying to achieve – here’s what I actually wore in Italy.
1. A Dark Midi Dress (In 100% Cotton Poplin)
similar dress | my current fav wear-everywhere sandals | boys’ button-ups and shorts from J.Crew
These dark midi dresses – done in cooling cotton poplin or linen – are the ultimate travel dresses. The breezy shape (and fabric) kept me cool on scorching Roman afternoons, while the dark hue cleverly hid inevitable gelato mishaps (oops haha). My dress still felt elegant at dinner, yet was comfy enough for strolling cobblestone streets.
similar dress | my current fav wear-everywhere sandals | boys’ button-ups and shorts from J.Crew
Shop Dark Midi Dresses
Think: romantic, Italian vibe in a cool, natural material.
2. Animal Print Dress (Leopard, Zebra, Etc)
I always love a good animal print, but I especially love a good animal print in Italy. There’s something timeless about these classic, glamorous prints, and they definitely feel right at home in Italy. Because my personal style tends to lean a little casual, I prefer leopard prints in casual silhouettes and comfortable, natural fibers (like linen and cotton). A little mini dress similar to this one was the perfect move for my trip to Italy (and here’s another really good option).
I wore this dress exploring Rome, wandering through Ortigia’s markets by day and sipping negronis at night – it’s ridiculously versatile and soooo perfectly Italian.
Shop Leopard Print Dresses
Pair any of these dresses with sneakers, sandals or heels.
3. A Dress With Sleeves
I waffled between what was the most important: the sleeves or the color of the dress? I bring a white dress on every summer trip to Europe (and haven’t regretted it yet), but for Italy, I want to talk about the sleeves.
Sleeves are not strictly necessary in Italy, but, if you plan on visiting churches – which often require women to cover their shoulders – it’s nice to have one sleeved option. (Throwing a lightweight silk scarf in your bag also works just fine with strappy sundresses, too.)
Since this is Italy we’re talking about, the sleeved dresses I gravitate to are still romantic in nature – think Shakespeare’s Juliet. I’d personally leave anything overly flowy at home.
Shop Pretty, Feminine Dresses With Sleeves
Hark! What light through yonder window breaks?
4. A Floral Romper (or Jumpsuit)
This 100% silk romper was kiiiiind of a find: years ago, on a random sale rack (at Intermix -does that store actually exist anymore?). But what I learned from wearing this jumpsuit in Rome was that having some sort of beautiful pants option was actually pretty nice – especially if you’re chasing kiddos around.
There’s also something about a jumpsuit (or a romper or – frankly – a matching set) that just feels…fun. It’s as statement-making as a really great dress, but playful, too. On subsequent vacations, I’ve found myself including at least one romper/jumpsuit/matching set option, and while it’s never been my most-worn piece on any vacation, I’ve always been really happy that I packed it.
Shop Jumpsuits, Rompers or Matching Sets
The more dramatic (or playful) the better. Says me.
5. Trouser Shorts
similar tee | shorts (old A.L.C.) – here’s similar
I’m a denim cut-offs girl, but Italy is NOT the place for cut-offs. Like…ever. Instead, a pair of black, trouser shorts was the perfect swap. Pair these shorts with a pretty top and leather sandals and you have the perfect outfit for all kinds of Italian adventuring – even if the “adventuring” is just ice cream for breakfast. 😉
similar tee | shorts (old A.L.C.) – here’s similar
Shop Black Trouser Shorts
Can be linen, but MUST be tailored.
6. A Long, Sexy Dress
Day dresses are great. And I could’ve gotten by with only day dresses – most of the time, I would just roll into dinner in whatever I was wearing. That said, it was really fun having a dress to wear at night that made me feel really sexy.
Sidenote: in the evening, I did feel a little more comfortable in longer dresses, but that might just be because we spent so much time in Sicily (which is a little more conservative).
Shop Sexy Dresses For Italy
This old thing?
7. Matching Lounge Set
I pack loungewear on every trip. Sometimes I wear it on the plane, sometimes I don’t, but I never leave home without it. The set I wore to Italy was a limited-edition set we designed with Voloshin (the folks behind Printfresh), but I also wear the heck out of my Frank & Eileen travel set (sooo pricy but a zillion times worth it).
Shop Comfy Matching Sets
Out of office.
8. Vintage-Inspired Swim
For Italy, I went with swimwear that had a nostalgic sort of charm. Think: high-waisted bottoms, strategic ruffles, leopard prints and maybe a polka dot or two.
exact suit: Mara Hoffman Kia (old, Poshmark only)
I wore mine lounging on rocks, jumping off swimming platforms, and hanging at the Baiamuri Beach Club. We even took the kids on some sort of spa “journey” at QC Termeroma that ended up being tons of fun (the hotel happens to be reallllly close to the airport, too).
Shop Vintage Inspired Swim
Hey, Doll.
9. Classic Cover-Up (Borrowed From Hubs)
cover-up (MikeD’s shirt)
Truth be told, I had forgotten to pack a cover-up, but nothing that fit the romantic, Italian vibe better than my husband’s button-up. A happy accident.
That’s it! That’s what I packed for Italy! And when we do go back some day, I’ll probably pack very similar pieces (if not the exact same). The biggest change?
PAX. OMG.
Gahhhhh gotta soak up those memories. It really does go by so fast.
xo,
S
 family vacation to Rome and Sicily—including the dresses, swim & comfy-chic outfits that actually worked.){kind=link}