Escape the Winter Blues With These Resort-Ready Pieces

collage of resortwear

Graphic by KCM

Were you even vacationing if you didn’t wear a cute sundress?

It seems like everyone is fleeing the cold weather in favor of tropical getaways. Our Instagram feeds are filled with friends and family escaping to Bali, the Bahamas, and beyond, and if you’re one of the lucky ones doing the same, we’re very jealous. Not only are warmer vacations inherently relaxing (unless you’re sightseeing and sweaty), but they also give you the chance to show off your favorite beach-ready looks — especially if you’re someone who believes that Tomato Girl Summer is forever.

Resort style is arguably the most fun to pack for, allowing you the chance to experiment with tropical prints and incorporate punchy accessories like a straw tote or colorful sandals you may not typically wear at home. If you’re anything like us, your itinerary has an outfit assigned to every activity. And if you feel your current wardrobe is lacking, we’ve come armed with inspiration.

So book a beachfront all-inclusive resort on an exotic island and stuff your suitcase with these vibrant prints, wedge sandals, and more staples that will make you look and feel like Monica Bellucci.

The Best Vacation Outfits and Resortwear for 2025

J.Crew Ruched One-Shoulder Swimsuit

J.Crew

Any trip is the ultimate excuse to buy a new bathing suit. This one-piece is a showstopper, and the ruching hugs your curves just right, giving you a confident, polished look whether you’re lounging by the pool or strolling along the beach. With the elegant one-shoulder design, you’ll feel effortlessly stylish and totally at ease. In this hue, you’ll match the sea, but you can stand out or blend in even more with one of the other colors.

We’ve got more great swimsuit options for mature women here.

$37+ at J.Crew

Spanx AirEssentials Half-Zip Pullover

Spanx

Katie doesn’t leave for the airport without this Spanx sweatshirt (and the matching pants), which she loves for its breathable fabric and polished look. If you’re in need of a put-together yet cozy travel outfit, you’ve found it. This gray color is also on sale, so snap it up before it sells out (as it often does).

$69+ at Spanx

Clare V. L’Été Tote

Clare V.

Headed to the beach? Create the most on-point outfit ever with this tote emblazoned with the French phrase “à la plage” (for the non-Francophiles, that means “to the beach”). We clicked on it for the crochet style and punchy colors, but the size sealed the deal. If you’re the type of person who needs many things to enjoy the sand, this oversized bag ensures you won’t have to make any compromises.

$185 at Clare V.

Farm Rio Sicily Flowers Shirt Dress

MyTheresa

Get ready to be a compliment magnet in this absolutely perfect sundress. It walks the line between casual and formal because it can be worn on the beach and off, with a fit-and-flare silhouette that you’ll always be comfortable in. This romantic number might become your favorite purchase of the year.

$350 at MyTheresa

lululemon Everywhere Belt Bag

lululemon

A secure purse is absolutely essential when traveling, which is why lululemon’s belt bag is seen all over airports. It fits firmly across the body, meaning all of your important belongings, like your wallet and passport, will be close to your heart and right in front of you, making it harder to pick pocket.

$38 at lululemon

Gucci Square Sunglasses

Nordstrom Rack

Sure, you could pack four pairs of sunglasses to match all your pre-planned outfits…or you can choose one timeless, versatile pair that will elevate or subtly complement each outfit you pair them with. The fact that you can wear these with almost anything justifies the investment.

$250 at Nordstrom

Birkenstock Madrid Big Buckle Slide Sandal

birkenstock madrid sandals

Zappos

Sandals and slides have a reputation for being more uncomfortable than sneakers. But Birkenstock changed the game when they released their corked soles back in the 60s. They’re no longer considered crunchy (not in a bad way, at least) thanks to the newer designs — and a renewed appreciation for comfortable footwear. This modern iteration of its cult classic sandal is the perfect example with one oversized buckle and turquoise leather.

Coach Double Zip Wallet

Coach

Travel tip: Pack your essentials in a smaller wallet to save space in your carry-on. This tiny yet mighty wristlet is slimmer than what you might require every day at home — those nail salon and café loyalty cards take up a lot of space — but will fit everything you need as you explore a new country. It has a double-zipped pocket, so you can easily separate your U.S. dollars from local currency.

$60 at Coach Outlet

Tory Burch Silicone Apple Watch® Watchband

Nordstrom

If your phone is buzzing from the bottom of your purse, you’ll appreciate the smartwatch 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 upgrade on the standard Apple Watch band, which is made of waterproof silicone in case you’re in the splash zone (i.e., watching the kids play in the pool).

$98 at Nordstrom

Walker and Wade Rio Maxi Skirt

Walker and Wade

There’s nothing quite as versatile as a stretchy maxi 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 the boardwalk to the 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 the secret to easy packing. All you need to do is tug the skirt up and wear the ruched bodice around your chest and you’ve got yourself a strapless maxi dress.

$298 at Walker & Wade

Beyond Yoga Spacedye Court Appeal Mini Dress

Beyond Yoga

Maybe you’re like Katie, where an ideal morning is spent on the pickleball court. 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.

$118 at Beyond Yoga

Terrain Cotton Crusher Hat

Anthropologie

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).

$38 at Anthropologie

Sorel Joanie IV Y Strap Wedge

Zappos

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 also get Katie’s approval because they provide a couple of extra inches of height.

$130 at Zappos

Jenni Kayne Cotton Hayes Crewneck Cardigan

Jenni Kayne

Just because your destination is warm doesn’t mean there won’t be an unexpectedly chilly night. We always pack an emergency cardigan, and we’ve never regretted it. At the very least, you’ll probably whip it out on the plane. We’ve raved about Jenni Kayne’s cashmere cocoon sweater ad nauseam, but when the beach breezes hit, we’ll be wrapping ourselves up in a cotton variation that’s shorter and more appropriate for higher temps.

$325 at Jenni Kayne

lemlem Gasira Caftan

Lemlem

Did you even go to the beach if you didn’t wear a whimsical, colorful coverup? Tropical destinations basically require you to wear bold colors you don’t typically wear back home, and this item checks off all the boxes without taking you far out of your comfort zone.

$225+ at lemlem

Quince European Linen Short Sleeve Shirt

Quince

Linen and sweaty temperatures go together like salt and the brim of a margarita glass. This breathable textile is great for keeping you cool, and it makes you look effortlessly sophisticated, too.

$35 at Quince

Quince 100% European Linen Shorts

Quince

Speaking of linen, why not wear a matching set to take the guesswork out of planning an outfit from your suitcase? This pair of shorts has a longer inseam, which creates a relaxed feel, but more importantly, the surprisingly sturdy material prevents your thighs from chafing as you spend the day exploring à pied.

$30 at Quince

Line in the Sand Splash Around Sun & Swim Dress

Line in the Sand

Go from a walk on the beach to brunch on the boardwalk in this dual-purpose dress. Long sleeves keep you protected from UV rays, and 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. This style is made from UPF fabric that boasts 50+ SPF protection, ensuring you can have fun under the sun without worrying.

$165 at Line in the Sand