The 5 Best Hawaii Vacation Outfits for 2022

One of the best parts about every vacation, in my opinion, is shopping and planning your travel outfits–especially if it’s for a special occasion. Imagine my excitement packing for my recent anniversary trip to Honolulu, Hawaii. Goodbye responsibilities—aloha to sundresses, swimsuits, and sunnies!

My partner and I spent a week together on the island. I had to be prepared for all the hiking and beach days ahead. I researched the best options in tourism activities, from the best running shoes for the trails to the most romantic dress inspired by an island (and yes, it was all possible with one suitcase).

To help you plan every ensemble for your next tropical vacation–whether you’re planning your honeymoon, an anniversary trip, or a romantic getaway ‘just because’–I’m sharing everything I bought for my Honolulu adventure, as well as how I styled each look.

These are the best Hawaiian vacation outfits.

This top is my favorite Amazon workout apparel. This tank top is flattering, comfortable, and affordable. I was drawn to the pretty shade of green, which can be worn outdoors with any bottom.

A pair of black running shorts is a must-have for any workout wardrobe. This pair features a front pocket that easily fits a pair of keys, a phone, or a small credit card holder–ideal for hikes or activities when you don’t want to lug around a purse or large backpack.

These Allbirds are my favorite running shoe. Featuring ripstop fabric, grippy treads, and stabilizing support, they’re specially designed for off-road terrain—which makes them ideal for hiking and trail running. They are stylish, and very comfortable.

How I styled it:

Chloe Caldwell


I hiked two miles in pouring rain.Hawaii Weather can be unpredictable. This outfit lasted the test of time! This sporty look was easy to wear with a low ponytail. It highlights the outdoorsy style.

I’m a sucker for a good set–you get a full outfit in a single purchase! This pink striped button up and matching shorts are super comfy. adorable for endless vacation photos. This is it ‘fit was perfect for all occasions, from riding around Honolulu in a Vespa to browsing the local shops.

How I Styled it:

Chloe Caldwell


The pretty pink hue is enough to make this outfit stand out by itself. I wore a simple white tank and my hair was in a high ponytail.

This dress is a total stunner! The front cut-outs are sexy and fun—perfect for a romantic getaway—and the vibrant green color is utterly on-brand for any tropical destination. For the perfect date night look, pair it with simple heels.

Tan heels are a staple in every wardrobe You should always have a spare set of hands! It’You can easily mix and match outfits for different occasions with versatile items. This pair from Steve Madden will go with any outfit on vacation.

How I styled it:

Chloe Caldwell


After a day of sun, sand, and ocean, I felt like dressing up for a special dinner. I styled this gorgeous green dress with flower hair clips–I bought mine at a local gift shop–and Lose your curlsKeep the theme alive with tropical vibes.

A swimsuit cover up is always a good idea. Princess Polly’s knit option provides adequate coverage, whether you are walking to the beach or relaxing by the pool. It’s easy to slip on between dips into the ocean because of its round neckline and stretchy fit.

These white sandals have become my favorite. They’re easy to slip on, so they became my go-to shoes throughout the trip. The leather material elevates a simple style, no matter if you’re walking around town or going to the pool.

How I styled it:

Chloe Caldwell


This is the perfect outfit for swimming pool. You will only need a pair sunglasses and a swimming suit. I wore mine loosely, with loose waves to create casual, laid-back style.

It is impossible to travel to Hawaii without visiting Hawaii. MinimumOne new bikini top! This bikini top is a great choice for any beach day because of its funky striped pattern and a central gold ring. It features adjustable coverage, tie straps, and removable pads to provide comfort and a snug fit. The best part? This eco-conscious pick is made sustainably using recycled nylon

Sun protection is essential for any tropical vacation. This hat can be carried in a bag and is much more portable than large sun hats. It still provides adequate coverage. It’s also super cute! It can be paired up with your favorite sunnies.

A Tropical vacation This is the perfect moment to have some fun and enjoy your sweetheart. These sunglasses add color to any outfit. They also protect your eyes against the harmful UV rays.

How I styled it:

Chloe Caldwell


I loved how the sunglasses’ orange frames matched my bikini top’s colors. To complement my suit’s center gold ring, I paired this beach look with gold hoop earrings.

Why should you trust Brides?

Chloe Caldwell is a Commerce Writer for Brides who specializes in shopping and lifestyle topics. She has more than five years of journalism experience in writing about fashion and beauty as well as travel and wellness.

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