I Went to Italy and Greece for Two Weeks—These Were My Best Looks

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. This is why I jumped on the first decently priced flight to Italy I caught 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 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 it into 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 from my European trip and where to shop each piece, keep scrolling.

Look #1: Roman Rooftop Dinner

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-risqué pieces (its cutout dresses are cult items) and was perfect for the occasion. 

Shop the look:

Look #2: Sightseeing in Florence

It's true that toile has 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.

Shop the look:

Look #3: Aperitivo Hour

LPA famously draws inspiration from 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. 

Shop the look:

Look #4: Lunch in Santorini

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. 

Shop the look:

Look #5: Pool Day in Greece

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 is one of my favorite swimsuits I own.

Shop the look:

Look #6: Having Gelato While Roaming in Florence

It's no exaggeration to say I ate my body weight 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 like 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.

Shop the look:

Look #7: All-White Grecian-Resort Vibes 

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.

Shop the look:

Look #8: Late-Night Spaghetti in Florence

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 cutouts are the obvious centerpiece here, but they weren't so risqué that I felt self-conscious. Paired with diamanté hoops, this was one of my favorite looks of the bunch.

Shop the look:

Look #9: Shopping in Oia

One of the main towns 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.

Shop the look:

Look #10: Alfresco Dining at Dusk

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 fringed hemline adds extra pizazz that really makes it stand out. I'm genuinely considering getting this in a second color.

Shop the look:

Look #11: A Day at Sea

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.

Shop the look:

Shop my packing essentials:

Up next: 6 Current Shoe Trends That Work the Best for Travel