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Outfits for Hawaii: 5 Essential Pieces

Updated: Oct 20th, 2021

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Traveling to Hawaii but not sure what outfit to wear? You’ve come to the right place! I often find myself scrambling to put together the perfect outfit before a trip. And after finding a few cute things I’d wear for different occasions, the challenge then becomes packing those pieces all into one suitcase. Through trial and error, I’ve finally found a few of my go-to sites for vacation clothes. In this post I’ll share 10 outfits for Hawaii that caught my eye as I was preparing for my trip to the Big Island.

1. Day-to-Night Sandals

A trip to Hawaii will likely involve some time on the beach or a casual stroll by the water, so a pair of cute sandals is a must. In fact, I bring sandals with me on almost every vacation because they’re super versatile – they allow my feet to stay comfortable for longer walks, they go with dresses, shorts, and jeans, and they let my feet breathe. Here are some sandals that caught my eye recently.


Low Heeled Crossed Leather Sandals

A simple pair of neutral-colored sandals is one of my favorite things to wear on a tropical vacation.

I love how you can easily dress up or down in them. I could wear these to the beach or wear them with jeans and a nice blouse for an ocean-front cocktail.

Having something so versatile means I can pack one pair of shoes and save space for essentials or other accessories.



Quilted Faux Leather Square Toe Slip-On Sandals

This year’s trends were all about pastels!!

If you’re visiting Hawaii during the spring or summer, this pair of mint green leather sandals will be sure to make your outfit for Hawaii stand out.

I love to wear a simple white tee and blue jeans sometimes, and having a pair of colorful sandals to go with my outfit helps elevate my whole look.



Faux Patent Leather Slide Sandals

I’m only OBSESSED with the color of these sandals. Imagine wearing these on the sand, or putting these on for a nice dinner at the resort you’re staying at. These sandals are so easy to dress up or down and the color makes it super easy to match.


Since shoes can be bulky to pack, the number one thing I think about is how many outfits I can wear them with on vacation. These three sandals can all be easily dressed up or down, and they will make for a good staple in your outfits for Hawaii.

2. A Maxi Dress or Two

I always pack a maxi or midi dress when I travel to Hawaii. It’s the perfect thing to wear to a restaurant by the beach, and if it’s in your plans, the perfect thing to wear to a luau.

When it comes to picking the perfect dress, I say just go with what you’re comfortable with. The important thing is to wear something that has a lot of give because you’re likely going to be devouring delicious Hawaiian food in that dress. Secondly, find something that’s flowy. Flowy dresses and beaches are simply a match made in heaven.


Ryden Dress

This dress comes in six different colors, but this one pictured to the right is by far my favorite. The colors remind me of the Hawaii sunset and I love the asymmetrical button details. This dress is also flowy but snug enough at the waistline that it’s still flattering.


luau outfit for hawaii


Away On Vacay Green Floral Print Two-Piece Maxi Dress

If you’ve been researching maxi dresses to add to your outfits for Hawaii for a while now, you might’ve noticed that they start to look similar after a while. When I came across this dress, the two-piece design immediately caught my eye. I also love that the the floral pattern isn’t consistent throughout, giving the dress a more natural and modern look.



Blooming Vision Black Floral Print Satin Maxi Dress

I love having splashes of color in my outfits, but sometimes I just want to go with something more subtle. This black dress is simple and still has that Hawaiian vibe with the pink flower prints.


lulus outfits for hawaii

3. A Stylish Hat

Hats not only make an outfit look more complete, they’re also great for sun protection and shade!

I like wearing a hat whenever chilling-on-the-beach-with-a-book is in the itinerary. Even though I always put on sunscreen when I go to the beach, having a hat provides the extra shade I need to be in the sun for an extended period of time.


Sunnydip Fray Boater

I’ve been on the hunt for a cute hat for a long time. I’ve come to the conclusion that the most flattering hats are the ones with a slightly wider brim. This hat fits that bucket perfectly, and the model looks super chic in that bikini-hat combo.



Joanna Beige Woven Straw Hat

Woven straw hats will go with just about anything. If you’re unsure which hat to get, you can’t go wrong with this reasonably priced woven hat from Lulus.


Hats can be very difficult to pack. I usually bring one hat and wear it onto the plane with me. Alternatively, you can stuff things inside the hat and around it then place it in your suitcase. This can prevent the hat from losing its shape or getting deformed while traveling in your suitcase.

4. Swimsuit You Feel Confident In

Your outfits for Hawaii won’t be complete without a swimsuit.

Even if you don’t swim, any gal’s packing list to Hawaii should contain at least one bathing suit. What if you want to chill on a chair in front of the pool? You got to have a look for that too.

My rule with bathing suits is that they have to make you feel confident first and foremost. No matter how cute a piece is, if it doesn’t make you feel confident and comfortable, there’s no point in buying it. Luckily, many retailers allow you to try on swimsuits with the sanitary sticker on. If they don’t, picture yourself wearing the piece first before buying and read a few reviews to see how others liked it.

bikini outfit for hawaii


Colorblock Tie Front Cut-out One Piece Swimsuit

It’s difficult not to like this bathing suit. The bottom portion is high waisted, and the colorblocking top piece is so cute! It’s got the prettiest combination of pink, white, and brick.

These days I love going with a high waisted bikini because it makes my legs look extra long.



Sophie Bikini Top & Highway Bikini Bottom

You can’t go wrong with a palm leaf print bikini set. This outfit has tropical and vacation written all over it. Similar to the Shein one-piece, it also has a knot for the top piece. This detail adds an elegance to the bathing suit and makes it look more modern.


revolve outfits for hawaii

Shein has become a new favorite of mine when it comes to bikini shopping. They don’t allow returns but their pieces are so affordable that for me it’s worth the risk to look cute! For any swimsuits I don’t end up liking, I try to turn them into a top to go with jean shorts or donate the ones that still have the sanitary stickers on.

5. A Pair of Sunnies

Like a hat, a good pair of sunglasses can add to your look. It can turn a simple outfit for Hawaii into an outfit that gets you lots of compliments. I’m a big believer that certain sunglasses will look better on certain face shapes, and there are a ton of guides out there that can help you select the best sunnies for your face shape. I have a hybrid heart-shaped and oval face so aviators and round sunglasses are what I typically go for.


Indio Sunglasses

These sunglasses are so cute they can be wore on your trip to Hawaii and beyond! These glasses come in this style pictured on the left and another one that has a cool deep blue mirror look to the lenses.


*Select colors currently on sale!


Leonard II E Sunglasses

Similar to the Madewell sunglasses, these round sunnies from Illesteva are so versatile they can be worn with your everyday outfit. They come in 12 (that’s right TWELVE!!) different colors so you’re guaranteed to find a shade you like.



Mykonos II Sunglasses

I currently have at least four pairs of sunglasses, and that’s a already a lot considering I’m trying to be as sustainable and minimal as possible these days. BUT if I were to get another pair of sunglasses, I think it’d have to be these. I love how lightweight these sunnies are, and the color makes the reflective lenses more subtle and elegant.


Outfit for Hawaii: All the Staples

I’ve traveled to Hawaii four times now, and picking out outfits has become one of the funnest parts of planning my trip there. For every trip, as long as I have a pair of sunglasses, a hat, bikinis I feel confident in, a maxi dress, and one pair of cute sandals, I’m 99% of my way there. Add a cute bag, some hiking shoes (sneakers will do if you’re a light hiker like me), your day-to-day tees and jean shorts, and you’re pretty much good to go!

I hope these five pieces will give you some inspiration on what to pack and where to shop for your next set of outfits for Hawaii.

If you’re struggling to figure out what to bring in your carry-on suitcase, check out my top 10 carry-on essentials.

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outfits for hawaii viv the wanderer

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