What to Wear in Hawaii: A Complete Guide

We just got back from our trip to Maui.  My husband and I had a trip planned in October to celebrate our 16th wedding anniversary, but quarantine struck and we had to cancel.  When some flight deals came up this spring, we jumped on it.  We had never been to Hawaii, so after securing childcare for the time we were away, the next most stressful thing was figuring out what to wear while we were in Hawaii.

I did some research and asked some experts (thanks, Sister), and packed my bag.  This post will hopefully help you know what to pack when you go to Hawaii.  Don’t have a trip planned soon?  No worries, now that all of these clothes have been Maui tested, I’m pretty sure I’ll be wearing them all summer.

And, maybe you are thinking, Michelle, this is a little bit of a deviation from your regular business content.  Yep, I know.  But, without my business, this trip wouldn’t have been possible.  Plus, I’m more than my business (and so are you!).  I want to make sure that this space I’ve carved out on the internet not only teaches you the ins and outs of business but also inspires you to live life more fully.  So, here we are, my guide to what to wear on your trip to Hawaii.

A complete list of what to wear in Hawaii:

3 swimsuits

2 cut of jeans

1 jean jacket

1 wrap dress

1 pencil skirt

4-5 t-shirts

1 sweatshirt

1 rain jacket

1 pair of jeans for the airplane

pjs

Flipflops

Chacos

Nice sandals

Every day sneakers

Exercise shoes, if planning on doing any big hikes that don’t involve water

A wide-brimmed hat and sunglasses

Snorkel, flippers, rash guards (swim shirts), and swim shorts

 

Which Swimsuits to bring to Hawaii:

You’re going to be at the beach or in the water for most of the trip, so bringing more than one swimsuit is a must.  I bought three suits.  Two I bought from Walmart.  I got the Cheetah one here and the striped one here and loved and the other one I splurged and got from Albion fit.  I like them all because they keep me covered while still making me feel great.  I’ve never spent too much time picking out swimsuits, but because of the trip, I took my time, ordered some suits, and sent back the ones that didn’t fit.  Having swimsuits that I felt confident and comfortable in was a game-changer.  You’re going to be wearing them most of the week so it is worth the time to find a good one and the money if you need to splurge.

I ended up loving the Albion Fit one the most because of the thick shoulder straps that you could wear off or on the shoulder.  They kept my shoulders covered from the sun.

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Which T-Shirts and Shorts to bring to Hawaii:

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Instead of an official swim cover-up, I opted for a t-shirt and shorts.  Then, when I was done in the ocean, I could slip on my shorts and shirt and go get dinner or a shave ice (or three).  Next to my swimsuit, t-shirts were my uniform in Maui.

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What Dresses to bring to Hawaii:

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The first night we got to Maui, we went to a Luau.  This wrap dress was perfect for the night because it was lightweight and didn’t wrinkle.  I also slipped it on after a morning snorkeling adventure and wore it for the rest of the day.

Having a simple pencil skirt paired with my t-shirts and a jean jacket was great for those sunset night walks.

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What shoes to bring to Hawaii:

My husband is a podiatrist, so we are pretty serious about our shoes.  I insist that the shoes are cute and he insists that they don’t hurt my feet.  After almost a decade of wearing podiatry-approved shoes, I’m hooked on buying shoes that take care of my feet.

Chacos: I wore these shoes the majority of the time because you can get them dirty in the sand or mud AND you can walk in the water with them.

Oofos flipflops: These are my house shoes of choice.  I wear them all day, every day at home, so I brought them with me to wear for casual walks on the beach and around our hotel grounds.

Mia Sandals: These sandals were my “fancy” shoes that I wore to Merriman’s for dinner and the Luau.  If you are short on room, you could get away with not bringing these.

On-Cloud shoes: I wore these shoes hiking up Haleakala.  If you are not going to do any of that kind of hiking, feel free to skip these athletic shoes when you are packing.

Ecco Slip-on Sneakers: I love these shoes so much.  For this trip, I wore them on the plane and when we were walking along the paths along the beach.

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What Accessories, Jackets, and Gear to bring to Hawaii:

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

We spent most of our time in the water with a snorkel and flippers on.  We bought the full face masks and I was very happy I had them.  Snorkeling was a struggle for me because I’m a bit claustrophobic.  So, when my face is covered and I can’t breathe like I normally do, I tend to panic. These snorkeling masks were a lot easier to breathe through than the regular ones that just cover your eyes and nose and by the fourth snorkeling expedition, I actually enjoyed it.

A wide-brimmed hat and sunglasses are a must for every beach day.  I also brought two rash guards to wear when I was in the water.  This kept me from getting sunburned and gave me a little extra warmth when the water was a bit cold.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

I also had a jean jacket that I wore flying and every night.  For our hike up Haleakala, I had a rain jacket which was so good because the winds were crazy and the weather was misty.  If you plan on making your way up Haleakala, you are going to need a jacket, sweatshirt, hat, and gloves.

This jean jacket from Old Navy is my favorite. 

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My trip to Maui was amazing.  The morning after I arrived, it started to rain.  I was disappointed, but luckily rain in Maui doesn’t last long and it also leaves the most beautiful rainbows across the ocean.  I just didn’t realize such a beautiful place existed and I felt so blessed to be there.  I hoped this helped you and that you now know what to wear in Hawaii.

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