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Packing is usually the thing I hate most about a trip. Figuring out exactly what kind of clothes you’ll need can be tricky…especially if it’s a place you’ve never been. Don’t worry friend…I’m practically an expert when it comes to figuring out what to wear in Hawaii. In this post I’m going to give you the lowdown on the weather in Hawaii, what the island style is like, and then give you some tips for what you’ll probably want to wear in different scenarios.
For a Hawaii packing list (including 26 specific things you don’t want to forget), read this post.
The Weather in Hawaii
It’s a tropical paradise year round, right? Well, pretty much. Hawaii is pretty temperate (not too warm, not too hot) year round, but their seasons technically match ours on the mainland. Our summer is their summer and our winter is their winter. “Winter” is a relative term in Hawaii, but what it mostly means are big waves and more rain.
While winter is the wet (and slightly cooler) season in Hawaii, most resort areas on the Hawaiian islands occupy the leeward (dry and sunny) side of the island. So even during the winter months, if you’re staying in Waikiki or Ko’olina on Oahu, Kona on the Big Island, Ka’anapali or Wailea on Maui, or Poipu on Kauai you can expect mostly dry, sunny, and warm weather. If you’re venturing to the north shore or any jungle areas of each island, you’ll likely experience more rain in the winter months (but that means it’ll also be lusher and greener and you’ll see more waterfalls and rainbows).
The difference between “winter” and “summer” is a bigger deal to locals than tourists. Unless you’re visiting the higher elevation areas of Maui and the Big Island (the upcountry), you aren’t likely to notice a difference in the temperature.
Temperature wise, the warmest months (highs in the upper 80s and lows in the mid 70s) in Hawaii are June through October while the coolest months (highs in the low 80s and lows in the mid 60s) are December through March. As you can see, there’s not a huge variation there and temperatures (both air and water) only fluctuate about 10 degrees year round. So if you’re coming from most places on the mainland, what you pack for Hawaii in September probably won’t differ too much from what you’ll pack for Hawaii in February.
Warm weather clothes are what you’ll need with some light layers as the trade winds can create a nice breeze in the evenings (especially if you’re out on or near the water).
Island Dress Code
I think most vacation destinations have their own personality style wise, especially if the majority of travelers visit from a concentrated area (you know what I’m talking about if you’ve visited the 30a area of Florida or places like Hilton Head or Palm Beach where everything is very preppy and Southern). But since Hawaii is very much an international destination, it’s a pretty eclectic place. Things are very casual and laid back and you’re likely to see people wearing pretty much everything, but when in doubt…dress down. Shorts and slippahs (flip flops) are respectable pretty much anywhere. Even the fanciest restaurants will only have a “resort wear” dress code, which basically means “try not to look like you just came from the beach.” Khaki shorts and aloha shirts for men and sundresses for ladies are about as fancy as you’ll ever need to get in Hawaii. 90% of your vacation can be spent in a swimsuit.
What to Wear in Hawaii
Now that you’ve got the gist of what the weather and vibe of Hawaii is like you should have a pretty good idea of what to pack. But I still get questions about what to pack or wear for specific occasions, so here are my recommendations for what to wear in Hawaii for 7 common scenarios:
What to wear in Hawaii…for hanging around the resort: The most stylish looking I ever see people in Hawaii is usually hanging around the big fancy beach resorts. It’s partly because 5 star resorts attract a certain type of people, but also because resorts are where you wear your…well, resort wear! If you’ve got a suitcase full of cute clothes and chic swimwear, the resort and the touristy areas are where you’re going to want to wear it. Sundresses, rompers, floppy sun hats, cute sandals, you know the drill. So whether you’re lounging around a cabana poolside, hitting the beach bar, or having a nice dinner, around the resorts and resort areas are where you’ll see people the most “dressed up” in Hawaii.
My #1 secret for what to pack to wear around the resort (anywhere in Hawaii actually) is the perfect coverup. In fact, my life is pretty much a mission to find the perfect coverup. Here’s some math for you: you’ll be in a swimsuit about 90% of the time you’re in Hawaii, but a good bit of that time you won’t actually be in the water or laying out in the sun. You’re going from your hotel room to the pool, or stopping by a local cafe for breakfast before you head to the beach, or running into a market for snacks in between snorkeling and driving to another part of the island to see sunset, or hopping from beach to hidden pool along the road to Hana. Basically there’s a lot of time where you always want your swimsuit on because you’re about to get in the water but you also want clothes on.
When you’re headed out in the morning, you won’t think much about putting shorts and a shirt over your dry suit, but as you’re in and out of the water throughout the day, you’re going to want something that’s light and airy to pull on over your head. Whether you’re at the resort, running from the beach/pool up to the pool bar for drinks, or stopping by a food truck after a morning snorkeling, you’re going to want something that’s easy to throw on over a wet swimsuit without having to put clothes on. I speak from experience.
Okay, that’s a lot about coverups but seriously…it’s the thing I tend to wear the most when I’m in Hawaii and also the thing I’m always searching for the “perfect” one. I usually always pack a few options to take with me, but I end up finding better stuff once I’m on island.
What to wear in Hawaii…for going to the beach: If you’re staying at a resort on the beach, you pretty much just put your swimsuit on and head on down, but if you’re staying in a house or condo where you’re packing up the car to drive to a beach (or just heading out to explore different beaches from where you’re staying), you’ll probably want to dress a bit differently. Read above about finding the perfect coverup because that 100% applies here. If I start the day wearing shorts and a tee shirt over my swimsuit, I’ll at least bring a coverup with me to put on when I get out of the water later. I always like having a set of dry clothes to throw on because I’m usually stopping to get snacks/shave ice/dinner/a new book to read before heading back to wherever I’m staying. Also, if you’re going to be out in the sun a lot (or doing something active like surfing, paddle boarding, or snorkeling), a sun shirt/rash guard is a must. And don’t forget the flip flops, hat, sunglasses, beach bag, etc.
What to wear in Hawaii…for snorkeling: If you’re snorkeling from the beach, you don’t really need anything special, but mostly I get asked about what to wear (or take with you) snorkeling when going out on a snorkel excursion on a boat. Here’s my routine: I wear my swimsuit, a pair of quick dry shorts, a long sleeve rashguard, and flip flops when I show up. Most boats don’t want you to wear any shoes on board so stick those in your bag. If the boat is loading from the beach (assume you’ll get wet from the waist down), I take off my shorts before I get on so I’m not starting the trip off cold and wet. I’ll wear my shorts on the boat, but I usually take them off before I get in the water. When I’m done snorkeling, I take off my rashguard, dry off with my towel (bring at least one for every person!) and then wrap up in a beach blanket (a thin blanket/towel I bought in Hawaii that I use way more than I ever thought I would). Once I’m dry (and warm) I’ll put on a dry coverup or shorts and tee shirt. After writing this, it’s now obvious that I spend a lot of my life avoiding being cold ; ) But trust me…people think “oh it’s Hawaii, it’s hot and sunny and I’ll just run around in my swimsuit” but once you get out of that 75 degree water, the boat takes off, and the wind picks up…you’ll be wishing you had warm, dry clothes. And maybe even a jacket haha. Keep in mind: most snorkel tours are in the morning because ocean conditions are calmer so it’s cooler plus they usually serve a light breakfast/lunch after snorkeling so you can be on the boat for quite a while after you’re finished snorkeling.
Besides what I mentioned above, you’ll want: hat (baseball cap kind not floppy kind that will blow away) and sunglasses, reef safe sunscreen (although the boat will most likely provide some), extra dry towels in the car for after, motion sickness meds, a waterproof case for your phone or a GoPro if you plan to take photos, and cash to tip the crew!
What to wear in Hawaii…for hiking: I’ll be honest upfront here…I’m not an avid hiker. I don’t really hike for enjoyment, I hike because there’s an amazing view, and it’s not possible to drive to get to it. So if you’re a super experienced, avid, hiked Kilimanjaro on your honeymoon type of hiker, you should probably ignore my advice. But I feel like it applies to 99% of people that “hike” in Hawaii. I don’t think you need “hiking boots” or shoes or whatever they’re called. Hawaii is not exactly a hidden destination and most of the best trails are pretty heavily frequented and maintained so you don’t need real heavy duty footwear. A lot of the trails tend to be muddy (or require crossing a stream), so I prefer Chaco/Keens/Teva sandals that can be washed off (but are still strapped to your foot). Clothes wise, I mostly just hike in shorts and a tee (I think it’s a bit warm for leggings but I see some people wearing them). A backpack is a must…you don’t want to be carrying around a purse or a tote bag. A lot of hiking trails are in jungly areas (where it tends to rain more) so a lightweight rain jacket is also a good idea. Pack: water, bug spray, sunscreen, guidebook, hat, sunglasses, snacks, etc.
What to wear in Hawaii…for Haleakala or Mauna Kea Summit: If you’re planning to go up to Haleakala (Maui) or Mauna Kea (Big Island), you’ll need to dress warm, especially if you’re going for stargazing or for sunrise since it’ll still be dark when you go up. And I don’t mean cold for Hawaii. It’s not uncommon for it to be in the 20s and 30s at that elevation (Fahrenheit). and is pretty windy so it feels even colder. Wear long pants for sure and layer up on top (you’ll want a fleece jacket at LEAST). I always pack a hat and gloves and warm socks plus take a beach blanket to wrap around myself to cut the wind. I know this probably sounds overly dramatic, but here’s the deal: 1) when you get in your car at your resort it’ll be in the 80s and when you get out of your car at the summit it’ll be in the 30s. Yikes. 2) It’s usually pretty windy so it feels much colder than the actual air temperature. 3) You’re not in and out of the car quickly. You’ll arrive at the summit when it’s still dark and you’ll have to wait 30-60 minutes for sunrise to start. 4) You’re not moving around-no hiking required-you’re just standing still.
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What to wear in Hawaii…for island exploring: If you’re just out and about around the island, sightseeing and what not, you’ll want to wear clothes that are cool and comfortable. Casual “knock around” clothes are what I end up wearing most often and depending if I have a lot to carry with me (book, water bottle, sunscreen, etc) I either like a small, lightweight backpack or a crossbody bag.
What to wear in Hawaii…nice dinner or a luau: Most restaurants in Hawaii are pretty casual (and even the nicer ones it’s okay to wear nice shorts and a top), but I usually like to wear a cute sundress and sandals just because it’s fun. Also, anytime I’m out at night (especially if I’m going to be on or near the water) I either like to wear something with sleeves or take a light sweater. Island breezes are no joke! For a luau…you will literally see people wearing anything and everything. Some people like to get dressed up in aloha wear and treat it like a special occasion and some people like to go casual.
Now that you’ve got the lowdown on what to wear, it’s time for the fun part…shopping! Everybody has their places they like to shop at home or online, but I thought I’d share some of my favorite places to shop IN HAWAII.
My Favorite Places to Shop in Hawaii
Target: Starting out with the obvious one. But Target in Hawaii is different! While summer stuff is seasonal on the mainland, they stock it all year round in Hawaii stores and they have a LOT of it. TONS of swimsuits, coverups, beachy clothes, hats, bags, etc. There are currently Target stores on Oahu, Maui, and the Big Island (Kona), and there’s plans to build one on Kauai.
Whaler’s Village (Maui): Right on Ka’anapali Beach, Whaler’s Village is the best overall shopping spot on Maui. It’s got some larger chain stores (Lilly Pulitzer, Lululemon, Sephora),all the major surf shops (Billabong, Roxy, Rip Curl, etc.), and some local Hawaii-centric shops (Blue Ginger, Olukai, Sand People, etc.). A lot of stores have Hawaii exclusive merchandise (Lily Pulitzer, Lululemon, Alex and Ani, Pandora, etc.). Olukai is a must for shoes and Sand People has everything from jewelry to accessories to housewares (most of it from local artists).
Ala Moana (Oahu): One of the largest and most luxurious outdoor shopping complexes in the world. It has everything you’d expect from a major mall plus some local shops and some international brands who have their only American presence in Hawaii.
Lululemon: This is my biggest share, so don’t sleep on it if you love Lulu…there’s an exclusive, customizable line that you can only get in Hawaii! There are two Lululemon stores on Maui (Whaler’s Village in Ka’anapali and Shops of Wailea) and one on Oahu (Ala Moana) and I’ve been told there’s a pop up in Poipu on Kauai. They have a variety of pre printed things (hats, leggings, tees, tanks, shorts, jackets, etc) in store ready to go, but you can also customize your order (pick the item, color, design, and placement) and pick it up the next day or they’ll even ship it to your house. Super fun!
Most of the places I like to shop in Hawaii are small boutiques or local shops that carry a lot of local artists or brands that you don’t find a lot of places on the mainland (at least not in Oklahoma ; ) Here are a few places I like:
Nuage Bleu (Paia)
Sand People (Ka’anapali)
Bikini Market (Wailea)
Bikini Bird (Kailua & Waikiki)
Guava Shop (Kailua & Haleiwa)
I Heart Hanalei (Hanalei)
P.S. Thanks for sticking around and reading this whole post! If you have ANY questions about planning your trip to Hawaii, you can join my free Facebook group here. I’m there answering questions every day and there are 7500+ other friends who have a ton of Hawaii information to share!
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