Feb 29, 2024

Best Vacation Clothes and Outfits for 2023

Graphic by KCM

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This season’s theme? La dolce vita.

If it seems like everyone is traipsing across Italy this summer, you’re not imagining it. According to Italy’s Ministry of Tourism, in June, Italy saw an estimated 8.6 percent growth in the number of foreign visitors arriving by plane, compared to the same period in 2019.

Our friends are sending us digital postcards (read: texts) from across the Amalfi Coast and random people we don’t remember following are filling our feeds with boat rides along the canals of Venice. And they all look amazing doing it thanks to Tomato Girl Summer. The viral trend encourages people to channel their inner Meditteranean through their style, and the aesthetic is filling shopping carts and suitcases all over the world.

But you don’t have to be bathing along the Italian Riviera to embrace this chic feminine look. It works anywhere, but especially with the carefree spirit that accompanies a vacation. Resortwear has been infused with this Euro-centric aesthetic, creating vacation wardrobes full of whimsy and sophistication.

Whether you’re heading overseas to a small seaside town or to a beachfront all-inclusive on an exotic island, stuff your suitcase with these summertime prints, wedge sandals, and more staples that will make you feel like Monica Bellucci.


Wear your heart on your sleeve and your favorite cocktail on your heart with this graphic tee featuring an Aperol Spritz. You’ll see this orange drink on the tables of every summer lover and tourist this year. But this tee is the soft and comfy antithesis to the bright and bitter drink. If summer 2023 had a cocktail pairing, this would be it.


Buying a beautiful new dress from DÔEN, a Los Angeles-based women-founded sustainable brand, feels amazing in more ways than one. This dress is made of GOTS-certified organic cotton voile, and looks great as a beach coverup, but you can easily add a leather belt and wear it to the resort’s happy hour, too. In this dress, you’ll feel breezy no matter how high the temperatures rise.


Get ready to be a compliment magnet in this absolutely perfect sundress. It walks the line between casual and formal, is made of a breathable cotton-poly blend, and has a fit-and-flare silhouette that you’ll always be comfortable in. This romantic number will be your favorite purchase of the year.


A secure purse is absolutely essential when traveling, which is why lululemon’s belt bag is all over the airport. It fits firmly cross body so it sits at your ribs, meaning all of your important belongings, like your wallet and passport, will always be in front of you.


Sure, you could pack four pairs of sunglasses to match all your vacation outfits…or you can pack one timeless, versatile pair that will elevate or subtly complement each outfit you pair them with. The Ray-Ban wayfarer is classic and cool, the perfect travel companion. And while they’re a worthy investment at full price, currently they’re part of Nordstrom’s annual Anniversary Sale. Snag them now before they sell out.


Katie doesn’t leave home for the airport without this Spanx sweater (and the matching pants), which she loves for its breathable fabric and elevated take on a hoodie. If you’re in need of a put-together yet cozy travel outfit, you’ve found it.


Travel tip: Pack your essentials in a smaller wallet for trips to save space in your carryon. This fire engine-red wallet is slimmer than what you might require every day — those nail salon and cafe loyalty cards take up a lot of space — but this small yet mighty wristlet will fit everything you need as you trail blaze across a new country. The red color will be easy to spot in your tote, and holding it with the attached strap will make you feel more protected.

Tory Burch

If your phone is buzzing from the bottom of your purse, you’ll appreciate the smart watch on your wrist that will provide you with essential updates without what could be considered an archaeological dig. Check your messages and track your steps in style with Tory Burch’s chic upgrade on the standard Apple watch band, which comes in a sunny yellow hue to match the summer weather.


Maybe you’re like Katie, where an ideal OOO is spent on the courts. Work on your backhand in this stylish workout dress, made with breathable technical fabrics and built-in shorts. It gets bonus points for being chic enough to spend the rest of the afternoon in while enjoying cocktails and conversation at the club.


We are sticklers for sun protection, which is why we reapply SPF throughout the day and always recommend a wide-brimmed sun hat. This cotton number will look great while you garden, but it’ll also stow away easily in your bag without wrinkling. It keeps the sun off your scalp, which we often forget to add SPF to (we’ve all experienced that flaky post-sunburn hair part).


Thankfully, you no longer have to suffer while wearing cute, strappy sandals. These Sorel sandals are a Wake-Up Call reader favorite, and we can totally see why. They have a cushy footbed that won’t cause your feet to ache at the end of a long day exploring big cities or island towns. They get Katie’s approval because they provide a couple extra inches of height.

Jenni Kayne

Just because it’s summertime doesn’t mean there won’t be an unexpectedly chilly night. Pack an emergency cardigan, just in case. We raved about Jenni Kayne’s cashmere cocoon sweater ad nauseum, but this summer, we’ve been wrapping ourselves up in the cotton version.


Did you even go on a beach vacation if you didn’t wear a whimsical, colorful coverup? Tropical destinations basically require you to wear bold prints and colors you don’t typically wear back home, and this item checks off all the boxes. This maxi kaftan comes in a swinging ’60s print reminiscent of Pucci, but it costs a fraction of the price.


A trip is an ideal excuse to buy a new bathing suit. Regardless of where you’re going, this timeless nautical swimsuit might just become your destination’s main attraction. The striped fabric and ruching on the torso are ultra flattering, and it can even act as a chic top under a pair of flowy pants or a skirt. If prints aren’t your thing, this same suit is available a dozen colors.

For more great swimsuit options for mature women, see our full story here.


You’ll be looking like a chic European no matter where you’re headed in these elastic linen shorts. They have a longer inseam, which creates a vintage feel, but more importantly, the surprisingly sturdy material prevents your thighs from chafing as you spend the day exploring à pied.


Sandals and slides have a reputation for being more uncomfortable than sneakers. But Hoka changed the game when they released their Ora slides, which are as supportive as their runner-approved Clifton sneakers, but are much more appropriate while sitting poolside. The cushy soles will support long walks, and the waterproof material will hold up against the sand and sea.

Line in the Sand

If you haven’t caught on yet, we’re all about easy summer basics you can throw on over a swimsuit or wear out to dinner during an evening out. This linen shirtdress will keep you cool and comfortable even on the most humid of days, thanks to the breathable material. Wear it on its own with sandals for a casual day look, or leave it open while you’re on the beach as a way to take a break from the sun’s rays.

There’s nothing quite as versatile as a wrap skirt. It’s the perfect beach coverup for days you aren’t in the mood for shorts and the best bottom choice for going from beach to restaurant in a flash. The most impressive designs can be styled as a dress, too, which is why we’ve been eyeing this one. Two-in-one clothing is they key easy packing. This skirt from Walker and Wade comes in a gorgeous orange botanical print that we suggest styling with an effortless white button-up top and strappy sandals.


This flowy number by Tommy Bahama is just as great on the beach over a swimsuit as it is on its own for dinner with a pair of espadrilles. Plus, its featherlight material can be rolled up and squished into your suitcase, so you don’t have to fear hitting the dreaded weight limit at the airport.

L.L. Bean

Whether you’re toting sunscreen and snacks or market-fresh flowers and souvenirs, this iconic bag will hold it all. L.L.Bean’s Boat and Tote is a timeless staple, made of sturdy canvas and contrasting handles. Feel free to customize it with your monogram or a cheeky phrase.

Line in the Sand

Go from a walk on the beach to brunch in this dual-purpose dress. Long sleeves keep you protected from the sun’s rays, but drawstrings on the side allow you to adjust the dress’s length for some versatility. Pull them up to create a tunic to wear with shorts, or leave the drawstrings loose to keep the dress looking more casual. It comes in five colors, too: Coral, green, white, gray, and navy. A big plus? 100 percent of the profits from this dress go to ocean and cancer organizations, so you’ll look good while doing good.


Finding versatile and multi-purpose clothing is the key to packing light without sacrificing options. A reversible dress that looks elegant no matter how you style it? Yes, please. This gingham number from Wayre isn’t only stunning, but it’s also made from recycled plastic bottles and spandex. Wear it forward and it’s a wrap dress with a deep v-neck, but turn it around for a high-neck dress with a cute waist tie.

He needs some updated vacation digs, too. This pair of swim trunks from Myoli Bay has a playful fish print all over. They’re made from recycled plastic and spandex, giving them a stretchy feel while retaining a structured look. A drawstring ensures he won’t lose his shorts when a strong wave rolls in, too.


Jumpsuits are absolute wardrobe warriors because they go with the flow of an action-packed travel day while keeping you comfortable. This cheery romper from Amazon will keep you covered on long beach walks while also providing plenty of room to eat all you want at your favorite vacation restaurant. Katie loves her jumpsuit collection, which Molner lovingly calls her “onesies.”

We all know a dress is a one-and-done outfit choice, but what if it could be more than that? This flattering frock has a built-in bra and shorts so you can wear it while exercising or bopping around town. Compressive fabric will keep you feeling supported all day long, while the shorts under the dress will ensure wardrobe malfunctions are nowhere to be found. And just in time for summer, Girlfriend Collective launched its ever-popular style in a summery yellow hue.

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