13 Best Tropical Vacation Outfits

Caroline Morse Teel is the Managing Editor for SmarterTravel Media. Follow her on Instagram @TravelWithCaroline.

Caroline joined Boston-based SmarterTravel in 2011 after living in Ireland, London, and Manhattan. She's traveled to all seven continents, jumped out of planes, and bungeed off bridges in the pursuit of a good story. She loves exploring off-the-beaten path destinations, anything outdoorsy, and all things adventure.

Her stories have also appeared online at USA Today, Business Insider, Huffington Post, Yahoo, Boston.com, TripAdvisor, Buzzfeed, Jetsetter, Oyster, Airfarewatchdog, and others.

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Warmer weather will be here soon. Be ready for it with these fun outfits that will make you feel like you’re on a tropical vacation.

Anne Cole Maxi Robe Coverup

Available in regular and plus size, Anne Cole’s Maxi Robe is the perfect cover-up for hot destinations. The robe style is one-size-fits-all, and simply ties in the middle, so you don’t have to worry about it clinging to you in the heat. Plus, the ultra-colorful sunset floral print will look great in poolside photos.

Tilley TOY1 Audrey Hat

For stylish sun protection, you can’t beat Tilley’s TOY1 Audrey Hat. With a four-inch brim, this hat will add a touch of glamour to any tropical vacation outfit. Made from 100 percent rice paper, the Audrey is lightweight but still provides UPF 50 sun protection. It’s lined with mesh on the inside and has a moisture-wicking sweatband to help keep you cool. There’s even a secret pocket on the interior to store your valuables.

Viscata Espadrilles

Add (comfortable) height to your tropical vacation outfit with Viscata Barcelona’s Roses Canvas Wedges. These on-trend espadrille wedge pumps add three inches of height via a 2 1/3 inch heel and half-inch platform that’s still easy to walk in. Made out of a soft cotton canvas lined with leather, these are some of the world’s most comfortable wedges.

Ably Valerie Maxi Skirt

Ably’s Valerie Maxi Skirt is a versatile item that can work for a long plane ride, as a beach cover-up, or as a part of a fun outfit in a hot climate where you want to remain modest. The skirt is made from a trademarked Filium activated fabric that repels liquids, stains, and odors, so you can wear it multiple times on one trip without needing to visit the laundromat.

Public Rec All Day Every Day Short

Public Rec’s All Day Every Day Shorts look casual, but they have plenty of serious features. Two front zipper pockets are deep enough to hold all your valuables, and two large back pockets hold anything you need easy access to. An elastic waistband makes these comfortable enough to wear on a long plane ride, or after a day of vacation indulgence.

Nisolo Serena Sandals

Nisolo’s Serena Sandals are the only shoes you need to pack for your tropical vacation. Available in three neutral colors, these minimalist sandals will go with everything—and they’re so comfortable you’ll want to wear them every day. A small three-quarter-inch wedge heel adds a little bit of support without causing pain and makes these sandals easy to pack. A cushioned insole, ankle strap, and soft leather lining add to the comfort factor.

Catalina Swim Bikini

No tropical vacation outfit is complete without a cute bikini underneath. Catalina Swim’s Twist Front Underwire Bikini Top and Hipster Bikini Bottom are flattering and comfortable. The twist front and ruching add a pop of style. The bikini top has underwire for extra support, plus removable cups and adjustable straps so you can get the perfect fit.

Belongsci 3/4 Sleeve Dress

This incredibly breathable dress comes in a wide variety of styles, colors, and sizes. This adaptable find is a cute and casual dress for any tropical occasion.

Milumia Plus Size Tropical Maxi Dress

Looking for plus size tropical vacation outfits? Check out Milumia’s Plus Size Tropical Maxi Dress which is available in sizes up to 3XL. The dress has a trendy cold shoulder design and a flirty split hem and comes in lots of tropical prints like palm leaf or florals.

Sanuk Water Shoes

Yes, water shoes can look stylish. In fact, you’d never know that these slip-on shoes from Sanuk are designed to be worn in the water—they look just like a cute beach espadrille. Made out of canvas with a rubber sole, these shoes are perfect for when you need to transition from the beach to lunch. They come in a variety of styles, including a men’s version.

KGB Running Shorts

Whether you plan on working out on vacation or just want something casual to throw on over your swimsuit bottoms, the KGB Running Shorts are a perfect choice. Available for men and women, these shorts hide a secret SmartSlot pocket in the waistband that’s large enough to hold a phone or wallet—or your sunscreen.

Halo AIR Series Headband

Tired of headbands slipping off your head whenever you do anything remotely active? Give Halo AIR Series Headband a try; it has silicone nubs on the inside to keep it securely in place. The headband offers UV protection, making it great to wear during sunny activities like snorkeling or hiking.

Poseshe Plus Size Maxi Dress

Nothing says vacation like a maxi dress. Poseshe’s Plus Size Maxi Dress is flowy without being frumpy, thanks to an adjustable waist tie that gives you definition. Made from a modal/spandex fabric blend, this dress travels beautifully and can be packed without causing wrinkles.

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Caroline Morse Teel is a Principal Editor at SmarterTravel. Follow her on Instagram @travelwithcaroline.

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