If all goes to plan, I'll be arriving at Milan Malpensa Airport in exactly 30 days, where I'll return 10 days later after I've sunned my way through the Italian Riviera—with stops in Santa Margherita Ligure, Camogli, and Portofino—and shopped my way through Milan. Everything's booked for my time actually in Italy. All I have left to do beforehand is pack my suitcase, which is proving to be the most time-consuming aspect of the trip by far.
I'd love to bring a trunk full of potential outfits, including accessories, shoes, and handbags for every possible occasion, but between the plane and train rides, checked-baggage fees and risks, and the fact that my boyfriend is bringing nothing but a backpack (typical), I'll have to do with just a carry-on. Luckily, I've become accustomed to packing light, even for long international trips that involve multiple stops and a variety of dress codes. So really, the only hard part is figuring out what sort of look I'll be going for and which items will bring my vision to life.
Below, scroll through the items that I think will do the trick.
Ever since I saw Sofia Richie Grainge wearing a very similar dress by The Row, I've been in love with the simplicity of a T-shirt dress and the way it can be dressed up and down with the help of great accessories.
Baby-pink shirting and a Mediterranean sunset? Count me in.
I love the idea of hopping around a beach club in these, a bikini, and the pink poplin shirt above.
They take up no space and will be perfect for days by the water.
When I tell you I've been searching for a white bikini that I actually like, I'm not kidding. It's a 24/7 job. But this Frankies Bikinis option from the brand's collab with Pamela Anderson feels like it could be the one.
Shop the matching Zeus Bikini Bottom ($85).
For the plane, I'm eyeing this big, structured tee from Jil Sander. Everyone on my feed has been wearing it, and I like the idea of pairing it with just a bikini or hot pants.
Duh.
Duh times two.
To be worn on its own or with a sheer skirt underneath to add some unexpected dimension.
My favorite look this summer has been a bikini with big earrings. These would also look amazing paired with a stretchy headband and a chic dinner outfit when my sea hair's too dirty to wear down.
Options.
I just ordered this gorgeous crochet set from Zara for NYFW, but I will absolutely be packing it for Italy as well.
Shop the matching Asymmetrical Crochet Skirt ($60).
I've wanted a pair of these for months, and as I approach my trip, I feel like I can't not buy them for it.
When it's a hot end-of-summer day in Santa Margherita Ligure, I'm going to be happy that I packed my favorite swim shorts/hot pants.
To be worn as a cover up, a top, a headscarf, a bandana, or a belt or around my shoulders. The options really are endless.
The perfect tank for traveling and, well, everything.
I'm not really a bra person, but I always bring one when I travel just in case. This one is so highly rated I had to get it.
My go-to travel pants are always drawstring linen trousers.
This is even bigger than it looks and will be perfect for toting around to the beach and the airport alike.
Sun protection is key to a successful vacation.
This tee can be dressed up and down with ease.
A must.
I never travel anywhere without at least one pair of jeans.
Even though this is a small bag, it holds far more than you'd think. My plan is actually to buy it when I get to Italy since I almost did last time I was there and went with the Sardine instead. I've thought about it ever since.
Even if it ends up being too warm to wear a sweater on my trip, I'll be happy to have it on the long flights and to use on a styling basis—around my waist or shoulders when my outfit needs a little something extra.
I always like to bring jean shorts on vacation, especially if it's summer and I'll be near the ocean. However, sometimes classic blue jean shorts can feel too casual. I love this white pair because there's no distressing on it, and with the right accessories, it can feel slightly more dressed up.
Since I already packed a silver pair.
Maillots are great for vacations because they count as both tops and swimsuits.
If it's sheer, I want it.
Underwear for every possible outfit.
I've been ogling this bodysuit for so long and think it would be a great statement item to pack. I also appreciate that it won't take up a ton of room but packs a lot of punch in the style department.
Everyone's wearing them.
For my one pair of dressy shoes, I'm opting for kitten-heel pumps that are super classic and will go with every outfit.
Another travel outfit that was inspired by Sofia Richie Grainge.
-
I Went to Seoul, Miami, and Chicago This Month—Here's Everything I Wore Along the WayAn editor's guide to packing for multiple trips.
-
9 Travel Destinations the Fashion Crowd Is Flocking to This YearFrom the glitzy Sardinian coast to this Hudson Valley hideout.
-
8 Destinations You Should Book for Summer 2025 and Packing Lists to MatchBook your flights now.
-
From Prada to Zara—30 Spring Items I Packed for 12 Days in TokyoI'm a Tokyo packing pro.
-
13 Things to Always Pack If Looking Like a Tourist Is Your Worst NightmareI'm right there with you.
-
Suddenly, Every Cool Person I Know Is Geotagging This Small Beach Town—Here's My GuidePinterest-viral hotels, intimate mezcal bars, world-class surfing, and so much more.
-
EmRata, Kendall Jenner, Vittoria Ceretti—Our Guide to the Island Everyone's Vacationing AtWhere to stay, dine, shop, and swim.
-
I Spent 5 Days at the Paris Olympics—Here's Everything I Did and WoreAnd ate and bought.
