5 Effortless Outfits for When the Plane Ticket Says "Hawaii"

Some of the most memorable vacations with friends and family that I've gotten to experience involved a flight to Hawaii. It might be a long day of travel coming from New York City, but being on such a beautiful set of islands feels like entering another planet, and there's so much to see and explore. I've done trips where I stayed at a resort and never left, and I've also had visits where I stayed with friends who live there and were generous enough to share what life as a local is like. With all that being said, I can't wait for my next visit, so of course, I'm already brainstorming my outfits.

On vacation, I usually gravitate toward dresses, but when I'm somewhere as effortless and low-key as Hawaii, I like to have fun with resort shirts, cutoff denim, and anything else that says "out of office." It's ideal to have pieces that you can easily throw on over any swimsuit of your choosing, and when you pack like that, the opportunities are endless. Keep scrolling to check out my set of inspiring outfits to choose from.

Woman wearing a pink bikini with a blue button down and a pink crochet hat.

(Image credit: @emilisindlev)

The beaches of Hawaii were made for outfits like this. A fun crochet bucket hat adds a retro, bohemian vibe, and the oversize blue button-down shirt creates a casual, effortless look that still pops. Pair them with a minimal pink bikini and you're ready to watch the waves roll in.

Woman wearing a crochet two piece set.

(Image credit: @annelauremais)

Wearing a crochet matching set in Hawaii exudes the kind of vibe that perfectly complements the island's laid-back atmosphere. The breathable fabric allows for comfort in the hot and humid climate, so you can feel as good as you look. Packing a straw bag for your trip is a must, and it goes perfectly with this look.

Woman wearing a red maxi dress.

(Image credit: @_sierramayhew)

Layering a bikini under a maxi dress is one of my favorite looks for a pool day if you're the kind of person who's looking for both style and practicality. When I know I'll be going straight from the pool to a casual lunch, this look never fails me. The combination allows for effortless movement and comfort, making it the perfect ensemble for enjoying a sunny day by the water.

Woman wearing a red baseball cap, a striped bikini top, a white button down, and white linen pants.

(Image credit: @lefevrediary)

If you're more of a city girl, I've found the look that combines casual beach vibes with an urban flair. I love how the red-and-white striped bikini top adds a pop of color. Linen pants and an oversize shirt are a must-have combination for an effortlessly chic look worn poolside.

Woman wearing a strapless red maxi dress and mesh ballet flats.

(Image credit: @nnennaechem)

A red maxi dress is the perfect choice for a nice dinner in Hawaii if you want to emulate a touch of island charm. This flowing silhouette complements the warm Hawaiian breeze, while the vibrant hue evokes the stunning sunsets over the ocean that are sometimes a shocking bright red. If this outfit isn't enough to convince you to book a flight, I don't know what is.

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Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, trying the latest fitness craze in New York City, or exploring luxury vintage boutiques.