What to wear on vacation in Hawaii

I already shared some of my Hawaii packing list on LTK, but here I’m going to show you what I actually wore on our recent trip to the Hawaiian islands. I didn’t go with the typical tank tops and shorts – I much prefer dresses for hot days! It’s a beach vacation, so your Hawaii vacation outfits can be as casual as you want them to be. I didn’t find the weather to be humid weather at all, and with the warm climate I tried to pack as light as possible.

We had a vacation rental for our first island and then a resort for the second. Both had a washer and dryer available so we were able to pack light (or as light as we could). I didn’t want to spend a lot of time doing laundry, but we also didn’t have much space in our carry ons for extra clothing. We did bring one checked bag, which included our hiking backpack and larger toiletries. We found that was the best way to bring what we wanted to while still making use of carry ons for the most part.

Pro tip: Put in an order at the local Target or Walmart to pick up on your way from the airport to your hotel! Our kids were waking up on east coast time and looking for breakfast at 4am, so that was a great way to have breakfast ready for them. (Read other tips in my other Hawaii blog posts!)

What I actually wore in Hawaii

For our long flight I dressed in sweats. We had a 13 hour flying day (plus airport time), and I wanted to be comfortable so wore the best clothes for that.

I totally forgot to grab my straw hat on the way out the door, but I did have a baseball cap with me that I wore on the beach when the sun got really hot.

This was the perfect hiking outfit for me! I was comfortable for all of our outdoor activities that day. (I have 2 pairs of shorts like this- they’re so comfortable!) I’ve now owned 5 pairs of sneakers in this style. They’re my favorite! And my favorite maternity t-shirt, which comes in a bunch of colors.

I realized that I packed 4 different navy blue dresses. Thrilling, no? You can take the girl out of New England… Here’s my new favorite navy blue dress that I found on Amazon, which I paired with white sneakers for a walk along the paved beach pathway one morning. (This dress comes in a bunch of different colors, and it also comes sleeveless/in a tank style!)

I packed 2 beach cover ups, which was perfect for this trip. This white flowy one was really comfy! Underneath I wore a 2-piece swimsuit, including my Hill House Swim top in purple gingham (currently on sale!).

P.S. Loved our hotel room – full review coming soon!

What I wore in Hawaii

Your Hawaii packing list for a 7 day trip

See my vacation packing list here!

• Light jacket, especially if you plan to go into the higher elevations at all. If you plan to do Haleakala National Park for sunrise, you’ll need a hat and gloves too.
• Light rain jacket if you’re there during the rainy season
• A hat for blocking the sun on the beach
• Flip flops
• Bathing suit x4 (I had one 1 piece and then 2-pieces which I could mix and match during the trip, which I found to be a great option)
• Swimsuit cover up x2
• Water shoes if your beach days will include any of the rocky beaches (or for the waterfalls on the Road to Hana)
• Rash guards for the sun
• Reef-safe sunscreen (a must!) to help protect the coral reef
• Maxi dresses or whatever your everyday wear is- personal preference! Hawaii leans toward casual clothing so leave your suit coats and high heels at home! A pair of linen pants and a crop top is perfect for going out to dinner. For our son’s “fancier” clothes I brought a couple of polo shirts and a pair of shorts. I found that bright colors were everywhere, so don’t be shy! I packed a dress for each day and definitely could have brought less in the clothing department. For men, a linen shirt and pair of shorts works.
• Pajamas and maybe a lounge set (I bought this lounge set from Amazon and loved it just as much as I did in Florida last year!)
• The best shoes for everyday are flip flops or slides (comfortable shoes for the beach and pool), plus a pair of sneakers. You may want hiking boots if you’re doing any of the short hike recommendations in the area. We did one of the waterfall hikes and I was wearing sneakers but wished I had hiking boots.
• Reusable water bottle (we used these the whole time)
• Credit cards (lol, but it’s true!)
• Hawaiian shirts if that makes you happy. We saw them all over the islands!

If you plan to do a boat tour or other water activities or water sports, you might want to bring along a waterproof phone case or a dry bag for your cell phone and other items.