The last time I went on a “real” vacation—the type where you completely unplug and don’t look at a screen even once—was about two years ago, so it was a long time coming. Hence why as soon as I caught a decently priced flight to Italy I jumped on it before I even had time to second guess myself. Through some finessing, I was also able to fit in a mini getaway to Santorini and Copenhagen while in Italy. Before I knew it a two-week vacation was born. This was my most extended vacation to date, and while great, a two-week trip also means a whole lot of outfits. You have to pack strategically. Thankfully I live for a vacation prep, so I carefully charted out my outfits weeks in advance. Keeping in line with the romantic Italian landscape and architecture, I knew I wanted pieces that evoked that La Dolce Vita feel, but with a slight edge. Bright colors and statement prints also were on my mood board, so several shades of orange, blue and green eventually made my suitcase. Ultimately I was able to fit roughly 16 outfits, five swimsuits, and five pairs of shoes in my Tumi suitcase (I highly recommend it for fashion people who love clothes), so it was a success in my book. To see all of the best outfits of my European trip and where to shop each piece, keep scrolling below.
Any meal on a rooftop is next level, but when that rooftop is in Rome, it’s unparalleled. For this evening I opted for an easy two-piece set with high impact from Christopher Esber. The brand has been my go-to for elegant meets risque pieces (its cut-out dresses are cult items), and was perfect for the occasion.
It’s true that toile has its origins in France, but there’s an essence about the print that also feels in line with Italy. Reformation has a whole collection of toile dresses for the summer, so it was an obvious choice to add to my vacation outfit lineup. This dress also received numerous compliments, which really says it all.
LPA famously draws inspiration from its founder Pia Baroncini’s Italian roots, so it made sense to wear this lemon yellow dress while exploring Rome during the aperitivo hour. The material is surprisingly lightweight so I never had to worry about sweating in the June humidity.
When I think of vacation, images of linen instantly come to mind. Few brands do sophisticated linen pieces like Cult Gaia—this dress is elegant and modern without looking too casual. The day I wore this was also exceptionally hot, and the linen held up through every sunbeam.
You’ll notice shades of blue everywhere in Santorini, and it’s not just the Aegean Sea. The color has a historical and cultural significance on the island, so naturally, I ended up wearing a lot of blue during my time there. It all melded perfectly with this suit by emerging designer Louisa Ballou which was one of my favorite swimsuits I ever owned.
It’s no exageration to say I ate my bodyweight in gelato. And in Italy, it’s practically a requirement. An all-white top may not be the best choice when downing a scoop of chocolate creamy goodness, but I made it work and felt letting the world see this outfit was worth the risk. I styled this halter top from cool-girl brand Area, with a printed Miaou midi skirt from its new collaboration with Paloma Elsesser. The entire look felt like the 2022 version of La Dolce Vita.
As much as I adore color, I felt like it was imperative to pack an all-white ensemble for my time in Greece. Another look from Cult Gaia made its way into my luggage (the brand is just so good for vacations), and I chose to wear this set during a sunset dinner on the beach. Everything was magical.
There’s always a time and place for an LBD, so even when I didn’t have an occasion in mind for this dress, I knew I’d end up wearing it at some point. The cut-outs are the obvious centerpiece here, but they weren’t too risque that I felt self-conscious. Paired with diamante hoops, this was one of my favorite looks of the bunch.
One of the main cities in Santorini, Oia is the site of the island’s famed elevated maze of walkways and whitewashed buildings. I was inspired by its bright landscape and wore this midi dress from indie label Asta Resort. Wearing bright colors feels like the definition of a getaway.
I’m not usually into the bohemian aesthetic, but I simply couldn’t stop thinking about this dress. Made with a heavier knit material, it’s great for chilly nights when you don’t feel like bringing a whole second layer, but want to stay cozy. The fringe hemline adds an extra pizazz that really makes it stand out. I’m genuinely considering also getting this in a second color.
Keeping it cool and casual for a boat trip on the Aegean Sea, I wore this bikini from Vix Paula Hermanny along with my beloved Asos cargos. Crochet is huge for the summer, so I brought along this JW Anderson tote to keep my sunscreen, snacks, and phone all in one place.
Good luggage is a non-negotiable for me. After going through several suitcases that ripped or busted at the seams, I decided to upgrade and have never looked back. I’ve had a Tumi for years and it’s well worth the place.
Traveling with this many outfits would not be possible without the assistance of these packing cubes. Going between five different cities during my trip, these cubes made the task of unpacking and repacking so much easier.
My flight to Rome included three different flights over the span of nearly 24 hours. My face would’ve broken out like no other without this for added hydration.
Simply the best lotion I’ve ever used. It definitely added to my vacation glow.
