The last time I went on a "real" holiday—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 trip 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 holiday 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 colours 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.
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My set may be sold out, but this bold blue co-ord has just as much impact.
Co-ords are perfect for travel as you can separate and mix with other pieces to create even more looks.
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.
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This elegant dress has a little stretch so there's always room for gelato.
The perfect finishing touch.
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.
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Love this sunny yellow.
The padded insoles allow for all day wear.
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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This gorgeous linen dress was my second choice.
Now these will go with everything.
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.
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It's all about the cut-outs.
Always accessorise.
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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I feel like Xtina would approve.
The Miaou skirt is sold out, but this graphic offering from Conner Ives is just as dreamy.
A truly classic style.
Look #7: All-White Grecian-Resort Vibes
As much as I adore colour, 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.
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This Alice + Olivia version will look great with anything from skirts to jeans.
A white skirt is so versatile.
Add a modern touch with bold accessories.
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.
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This is seriously elegant.
Evening looks call for a little sparkle.
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 colours feels like the definition of a getaway.
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Now this is bright.
There's plenty of colours to choose from, but this sea blue stole my heart.
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 cosy. The fringed hemline adds extra pizazz that really makes it stand out. I'm genuinely considering getting this in a second colour.
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I'll be wearing this every summer from now on.
Eyes on the sale price.
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.
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There's plenty of ways to wear this bikini top: halterneck, bandeau, traditional, criss cross.
Orange is big for summer 2022.
90's cargo pants are back - and oh so comfortable.
Add contrasting texture with this crochet tote.
Shop my packing essentials:
Good luggage is a nonnegotiable 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 price.
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.
This is simply the best lotion I've ever used. It definitely added to my holiday glow.
Up next: I Spent Four Days In Paris - Here's Everything I Packed And Wore
This story originally appeared on Who What Wear US.
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