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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Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.