The Best Resortwear and Vacation Outfits for Your Next Getaway

Vacation Outfits

Graphic by KCM

Here’s to a much-deserved week away.

If you’ve been affected by this arctic freeze that’s sweeping the Northern hemisphere or the snowstorms that are sprinkling other parts of the country, or winter just isn’t your season, you might be fantasizing about warmer times while dousing your driveway in salt. If any of this inclement weather has you heading for some grassy, sunny hills, you’ll need to start packing.

If you’ve put all your summer essentials in storage, or just want to refresh that wardrobe, you’ll need to read up on the latest resortwear trends.

Taking time off presents us with the rare opportunity to actually put our phone down, pick up a beach read, and forget about work. And even though we’re there to relax, going on a much-needed vacation is also a great reason to break out those pieces you haven’t worn in a while — or pick up some new ones. Sometimes, getting dressed on vacation is the best part. After all, it’s not every day you get to wear a kaftan to dinner. Whether you’re heading overseas to a small seaside town or to a beachfront all-inclusive on an exotic island, these vacation outfits and resortwear pieces will have you ready for the waves and sunshine.

From fun dresses to classy jumpsuits, slip-on sandals to flirty wedges, we rounded up 17 travel-ready items that deserve a spot in your tightly-packed suitcase.

The Best Vacation Outfits and Resortwear for 2023

Colorful Kaftan


Did you even go on a beach vacation if you didn’t wear a whimsical, colorful coverup? Tropical destinations basically require wearing 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.

$25 at Amazon

Coach Tortoise Sunglasses

Sunglass Hut

No vacation look is complete without a great pair of sunglasses. Reach for your favorite pair, or invest in a new one that suits your specific needs. This Coach cat-eye is not only gorgeous, but it’s intended for those with a high nose bridge and lower cheekbones (if your nose’s bridge begins above your pupils), so it’ll offer you a more secure and comfy fit that won’t fall off. You can also opt to add prescription lenses too, because sandy contacts can ruin a vacation.

$202 at Sunglass Hut

J. Crew Ruched Femme One-Piece Swimsuit

A trip is an ideal excuse to buy a new bathing suit. Regardless of where you’re going, this shotstopping, retro floral swimsuit might just become your destination’s main attraction. The ruching on the torso is ultra flattering, and it can even act as a flirty top under a pair of flowy pants or a skirt. If the flower print is too busy for you, the other bright colors options are equally exotic but a bit more muted.

$118+ at J.Crew

Everlane The Way-High Canvas Short

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

$60 at Everlane

Ora Recovery Slide 3


Every vacationer needs sandals that can easily be slipped on and off. These Hoka slides have the same comfort you love from their cult-favorite sneakers, but they are much more appropriate while sitting poolside. The soles are extra cushy to support long walks, and feel free to wear them to the beach since they’re made from a waterproof material.

$60 at Zappos

Quince 100% European Linen Pants


Bottomless brunch? Check. Beach cover-up? Check. Most comfortable pants in the world? Also check. These 100 percent linen pants have an elastic waistband that is both chic and extremely easy to wear. This price tag is also surprisingly low — similar pants typically retail for more than three times as much as this Quince pair, despite it upholding the same, amazing quality.

$40 at Quince

Mango Baroque Print Pants and Shirt


Some sets are just meant for vacationing in. The baroque print on this breezy pair of pants and matching shirt was made for sailing across the Amalfi coast or elevating a trip to your local lake. The silky material will pack away without wrinkling, and we’re positive you’ll want to snap some family pictures while wearing these photogenic shirt and pants, as a set or on their own.

$70+ each at Mango

Walker and Wade La Playa Skirt

There’s nothing quite as versatile as a wrap skirt. It’s the perfect beach coverup for days you aren’t feeling shorts, the best bottom choice for going from beach to restaurant in a flash, and you could even style it into a dress if you’re in a real pinch. This one from Walker and Wade comes in a gorgeous orange botanical print, which you could wear with just about anything. How amazing would this look with an effortless button-up top and strappy sandals?

$158 at W&W

Tommy Bahama Embroidered Long Sleeve Cotton Cover-Up Dress

You can never have too many easy, breezy sundresses. 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.

$138 at Nordstrom

J. Crew Straw Market Tote

Whether you’re toting sunscreen and snacks or market-fresh flowers and souvenirs, this bag will hold it all. Leather handles elevate the casual straw bag, which makes it feel a little more polished — and justifies giving it its own chair on the beach.

$118 at J.Crew

Line in the Sand Splash Around Sun & Swim Dress

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.

$155 at LITS

Wayre Roma Reversible Wrap Dress


Finding versatile and multi-purpose clothing is the kick 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 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.

$130 at Wayre

Sorel Cameron Wedge Sandal

Thankfully, you no longer have to suffer while wearing cute, strappy sandals. This pair from Sorel has a cushy footbed that won’t cause your feet to ache at the end of a long day exploring urban cities or island towns. There’s even a slight heel to give you a couple of extra inches of height. This pair could easily be worn during a night out to dinner or out on a quick trip to the surf shop.

$135 at Zappos

Myoli Bay Deep Sea Fishin’ Swim Trunks

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.

$48 at Myoli Bay

Anthopologie Cotton Crusher Hat

There’s no such thing as fun in the sun if you can barely see where you’re going. A cotton sun hat not only keeps the sun out of your eyes, but it protects the delicate skin on your face from sunburn. It also keeps the sun off your scalp, which we often forget to add SPF to (we’ve all experienced that flaky post-sunburn hair part). A wide brim ensures you’re well-covered, but the fun bucket hat silhouette keeps it from feeling too dated.

$36 at Anthropologie

Madewell Sophia Sweetheart Jumpsuit

Jumpsuits are absolute wardrobe warriors: Not only can they effortlessly go from beach to brunch, but they’re so comfortable that they feel like wearing pajamas. This smocked-top romper from Madewell will keep you covered on long beach walks, while also allowing you plenty of room to eat all that you want at your favorite vacation restaurant. It even has pockets! Katie loves her jumpsuit collection, which Molner lovingly calls her “onesies.”

$138 at Madewell

Girlfriend Collective Paloma Racerback Dress

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 to exercise in 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.

$88 at Girlfriend Co