I Went to Italy and Greece for Two Weeks—These Were My Best Looks (2024)

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 getawaytoSantorini 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 myoutfits 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 greeneventually 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 outfitsfrom 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.

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Look #2: Sightseeing in Florence

It's true that toile has origins in France, but there'san 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.

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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 whileexploring Rome during the aperitivo hour. Thematerial is surprisingly lightweight, so I never had to worry about sweating in the June humidity.

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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.

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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 hasahistorical and cultural significance on the island, so naturally, Iended up wearing a lot of blue during my time there. It all melded perfectly with this suit by emerging designer Louisa Ballou, whichis one of my favorite swimsuits I own.

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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.

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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. Anotherlook 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.

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Look #8: Late-Night Spaghetti in Florence

There's always a time and place for an LBD, so even whenI 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, butthey weren'tso risqué that I felt self-conscious. Paired with diamanté hoops, this was one of my favorite looks of the bunch.

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One of the maintowns 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.

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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.

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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 belovedASOS 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.

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