The 5 Vacation Outfits I Bought for My Anniversary Trip to Hawaii in 2023

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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. So you can imagine my excitement when packing for my recent anniversary trip to Honolulu, Hawaii. Goodbye responsibilities—aloha to sundresses, swimsuits, and sunnies!

My partner and I spent a full week on the island, so I needed to gear up for all the hikes, beach days, and dinners ahead. I researched tried and true options for various tourism activities, from the best running shoes for hitting the trails to the ultimate island-inspired date night dress (and, yes, I am proud of myself for fitting it all into a carry-on 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.

Read on for the best vacation outfits perfect for any Hawaiian getaway.

Best Outfit for Hiking

The Gym People Women’s Longline Sports Bra

I'm a long-time lover of Amazon fitness apparel, and this top is no exception. This tank top is affordable, comfortable, and flattering. I was especially attracted to the pretty shade of green, which is perfect for photos outdoors and simple enough to go with just about any bottoms.

Price at time of publish: $22

Blooming Jelly Quick-Dry Running Shorts

black running shorts amazon

Courtesy of Amazon

A black pair of running shorts is essential to every workout wardrobe, and a must on every vacation packing list! 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.

Price at time of publish: $30

Allbirds Women’s Trail Runners SWT

allbirds trail runners

Courtesy of Allbirds

These Allbirds have become my new favorite pair of running shoes. 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. Not to mention, they're equally as stylish as they are comfortable.

How I Styled It:

best vacation outfits

Chloe Caldwell

I hiked about two miles in the rain (Hawaii weather can be unpredictable, to say the least), and this outfit stood up to the elements in style! I wore this sporty ensemble with a low ponytail to stay comfortable and play up the outdoorsy aesthetic.

Best Outfit for Exploring

Princess Polly The Chloe Set Pink Stripe

pink strip matching set

Courtesy of Princess Polly

I'm a sucker for a good set–you get a full outfit in a single purchase! This pink striped button-up with matching shorts is ultra-comfortable and adorable for endless vacation photos. I wore this 'fit everywhere, from riding around Honolulu on a Vespa to perusing the local shops.

Price at time of publish: $68

How I Styled It:

pink stripe set vacation outfit

Chloe Caldwell

This outfit doesn't need much accessorizing, as the pretty pink hue stands out on its own. I threw on a simple white tank top and put my hair in a high ponytail to let this set do all the talking.

Best Outfit for a Fancy Dinner

Jagger & Stone Emily Maxi Dress Green

green cut out maxi dress

Courtesy of Princess Polly

This dress is an all-around 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. Pair it with simple heels for the ultimate date night look.

Price at time of publish: $100

Steve Madden Blake Tan Heels

steve madden tan blake heels

Courtesy of Steve Madden

Tan heels are a staple in every closet and in your luggage! Packing versatile items makes it easy to put outfits together for different occasions. This pair from Steve Madden will go with any dressy ensemble you bring on vacation.

Price at time of publish: $100

How I Styled It:

green maxi cut out dress

Chloe Caldwell

After a day in the ocean, sand, and sun, getting dolled up for a celebratory dinner was exactly what I needed. I styled this gorgeous green dress with flower hair clips–I bought mine at a local gift shop–and loose curls to stay on-theme with the tropical vibes.

Best Outfit for Relaxing by the Pool

Princess Polly Gardena Mini Dress White

white swim cover up

Courtesy of Princess Polly

It's always a good idea to bring a swimsuit cover-up on vacation. This knit option from Princess Polly offers adequate coverage whether walking to the beach or lounging by the pool. And the rounded neckline and stretchy fit make it easy to slip on between dips in the water.

Price at time of publish: $55

Cole Haan Florens Slide Sandal

white cole haan sandals

Courtesy of Amazon

I'm obsessed with these white sandals that are both comfortable and stylish. They're so easy to slip on when walking out the door, which made them my go-to shoe throughout the entire trip. I also love how the leather material elevates an otherwise simple style, whether you're heading to the pool or walking around town.

Price at time of publish: $78

How I Styled it:

white swim cover up

Chloe Caldwell

Your swimsuit and a good pair of sunglasses are all you really need for this pool-appropriate outfit. I wore mine with loose waves for a casual, laid-back look.

Best Outfit for the Beach

Princess Polly Layla Bikini Eco Nylon Top

brown striped bikini top

Courtesy of Princess Polly

It's not a trip to Hawaii without at least one new bikini top! The funky striped pattern and center gold ring make this a stand-out option for every beach day. It features adjustable coverage, tie straps, and removable pads for a secure fit and comfort. The best part? This eco-conscious pick is sustainably made with recycled nylon.

Price at time of publish: $38

FGSS Distressed Bucket-Hat

white bucket hat fringe

Courtesy of Amazon

Sun protection is essential to any tropical getaway. I love this hat because it's easy to pack in a carry-on (unlike large sun hats), but it still provides enough coverage. Not to mention, it's totally cute! Pair it with your favorite sunnies and you're good to go.

Price at time of publish: $7

SOJOS Retro 90s Rectangle Sunglasses

orange sunglasses

Courtesy of Amazon

A tropical vacation with your sweetheart is a perfect time to have some fun and experiment with your style. These colorful sunglasses add a vibrant pop to any outfit while keeping your eyes protected from those harsh UV rays.

Price at time of publish: $13

How I Styled it:

best vacation outfits

Chloe Caldwell

I loved how the orange frame of my sunglasses paired effortlessly with the colors of the bikini top. I paired this beach day look with gold hoop earrings to complement the center gold ring of my suit.

Why 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 writing about all things fashion, beauty, travel, and wellness.

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