When I first started packing for my Hawaii trip, I’ll admit I overthought everything. Should I bring heels? Would I wear that flowy dress? Do I need a jacket for the evenings? Now, after a few trips (and a couple of packing mistakes), I’ve figured out exactly what works and what just takes up space in your suitcase.
Whether you’re chasing waterfalls in Maui, sipping mai tais on Oahu, or heading to a sunset luau, I’ve got you covered. Here’s what I actually wore in Hawaii and what I’d pack again in a heartbeat.
Everyday Outfits for Island Exploring (Stylish Comfort from Sunrise to Sunset)
Most of my days in Hawaii started with a coffee run, followed by beach-hopping, roadside fruit stands, or wandering through a cute town. So, my go-to day outfits needed to be easy, breathable, and camera-ready with just enough style to go from breakfast to spontaneous detours.
What I wore and why it worked:
- Flowy sundresses: Think thin straps, tiered skirts, and island prints. These were light enough to handle the heat and looked effortlessly pretty in photos. I had a white one that worked great for sunrise beach walks and a floral one I wore while exploring Hanalei.
- Linen shorts + tank tops: My staple for walking through farmers markets or grabbing a poke bowl. I went for a neutral palette (white, tan, and sage) that made mix-and-matching simple.
- Matching co-ord sets (crop tops + skirts or shorts): These were a lifesaver on days I wanted to look pulled together without trying. I packed one in a tropical green and another in a soft blue and ended up re-wearing both.
Helpful tips:
- Choose natural fabrics like cotton, linen, or rayon to stay cool. Synthetic materials just trap heat.
- Pack neutral basics you can layer or rewear (especially if you’re island hopping with limited luggage).
- Toss a light kimono or scarf in your tote it’s perfect for chilly AC or modest temple visits.
Beach & Pool Day Looks (Where Cute Meets Practical)
In Hawaii, you’re never too far from a beach, waterfall, or infinity pool so I made sure my swimwear could transition from lounging to swimming to lunch without skipping a beat.
Beach and pool outfits I loved:
- High-waisted bikinis: These gave me coverage and confidence. Great for snorkeling, paddleboarding, and sunbathing without needing constant adjustments.
- One-piece swimsuits: I wore these when I wanted something a bit more supportive or when I planned to turn it into a full outfit by tossing on shorts. Bonus: less sunscreen area to worry about.
- Chic coverups: I had two, an oversized white button-down and a breezy black kimono. Both worked over swimsuits, at beach bars, or even as light layers in the evening.
Accessories that mattered:
- Wide-brim straw hat: Protected my face and gave me that classic island look.
- Polarized sunglasses: Trust me, these made a difference when kayaking or driving near the water.
- Beach tote with waterproof lining: To store wet swimsuits and sandy flip-flops.
Quick tip: Pack multiple swimsuits so you always have a dry one for the next adventure. They rarely dry fully overnight in the humidity.
Adventure Outfits: Hiking, Kayaking & Chasing Waterfalls
Hawaii’s natural beauty is unbeatable but it’s also wild, muddy, and often wet. I learned the hard way that fashion had to meet function, especially when hiking through rainforests or navigating slippery lava rocks.
Adventure-tested outfit combos:
- Moisture-wicking activewear sets: My go-to for waterfall hikes. Think spandex biker shorts or leggings with a breathable tank. The quick-dry factor really matters when you’re sweating or caught in a drizzle.
- Water shoes: Don’t skip these. From crossing streams to exploring rocky tidepools, they kept my feet protected and slip-free.
- Dry-fit T-shirts + athletic skorts: Perfect for days with mixed plans like a short hike followed by a casual lunch. Skorts were cuter than shorts and felt more breathable.
Pro gear tips:
- Bring a dry bag or waterproof fanny pack for your phone, cash, and snacks.
- Consider a packable rain jacket, especially if you’re in Kauai or doing sunrise treks.
- A light microfiber towel fits in any bag and was great after a swim under waterfalls.
Sunset Dinner & Luau Looks (Dressed Up, Island Style)
Evenings in Hawaii have a magic to them warm breezes, twinkle lights, and live music in the background. I loved dressing up a bit for sunset dinners, beachside bars, or a traditional luau. Nothing too fancy, but just enough to feel special.
Evening outfit favorites:
- Maxi dresses with island vibes: Mine were in bold prints and flowy cuts. I wore one in Wailea for cocktails and another in Kona for a romantic dinner by the water.
- Off-shoulder tops + midi skirts: The perfect combo of cute and comfortable. Add a wedge sandal or flat strappy sandal and you’re luau-ready.
- Halter jumpsuits or wrap dresses: I brought one black and one emerald green. They packed small and dressed up effortlessly.
Jewelry & glam:
- I kept it simple gold hoop earrings, a shell bracelet, and a small woven clutch were enough to elevate the look.
- For makeup, I stuck to BB cream with SPF, tinted lip balm, and waterproof mascara the humidity was no joke.
Pro tip: Skip the heels. Almost every place I went had sand floors or grassy lawns. Go for flat or low wedge sandals instead.
Travel Day & Airport Outfits (Comfort That Still Feels Cute)
Long flights, temperature swings, and that first moment of stepping off the plane into island air you want to feel comfortable yet vacation-ready. My travel outfit had to work for security lines and welcome photos.
What I wore on travel days:
- Joggers + cropped tank + denim jacket: The joggers kept me cozy, the cropped tank layered easily, and the jacket was great for the plane or chilly nights.
- Comfy sneakers or slide sandals: I switched between the two depending on how much walking I expected. Pro tip: wear your bulkiest shoes on the plane to save suitcase space.
Travel tips from experience:
- Keep your hat in your carry-on crushed hats are the saddest travel fail.
- Use a small crossbody bag inside your personal item for quick access to ID, lip balm, and earbuds.
- Always pack a swimsuit and a light outfit in your carry-on, just in case your luggage takes a detour.
Hawaii Packing Tips I Swear By
- Don’t overpack: You’ll live in swimsuits, breezy outfits, and sandals.
- Roll your clothes: Saves space and minimizes wrinkles.
- Bring reef-safe sunscreen: It’s required in many places and better for the ocean.
- Check your hotel’s laundry options: I rewore my favorites after a quick wash.
What Not to Pack for Hawaii
These are the things I brought but never used or wished I’d left at home.
- Heels: Sandals did the job beautifully.
- Heavy makeup: It just melted off.
- Jeans: Too hot and sticky most days.
What to Wear in Hawaii by Island
Every island has its own rhythm, and I definitely noticed how my outfits shifted depending on where we were.
- Oahu: The most cosmopolitan island, think trendy brunch spots, rooftop bars, and beach clubs. I wore cuter sets and flowy dresses here more often.
- Maui: A mix of resort chic and beachy casual. I loved maxi dresses in Wailea and stuck to relaxed linen pieces for days in Paia.
- Kauai: So laid-back. Most days, I lived in shorts and tank tops, especially on the north shore.
- Big Island: Pack for adventure. I wore activewear almost daily think hikes to waterfalls, volcanic craters, and black sand beaches.
If you’re island-hopping, bring pieces you can mix and match. That saved me tons of suitcase space.
What to Wear in Hawaii by Season
Hawaii doesn’t have four seasons like the mainland, but it does have some weather patterns to keep in mind.
- Winter (Dec-Feb): Expect a few more showers, especially on Kauai. I packed a light rain jacket and quick-dry shoes and was grateful I did.
- Spring (Mar-May): My favorite time. Warm days, cooler nights. Bring layers!
- Summer (Jun-Aug): Hot and humid breezy fabrics are a must. I practically lived in linen.
- Fall (Sep-Nov): Similar to spring but slightly drier. I wore the same outfits on repeat with a cardigan for sunset dinners.
What I Wish I Had Packed (and What I Regret)
Real talk? These were the hits and misses from my suitcase:
Things I Forgot but Needed:
- Water shoes: I slipped on wet rocks more times than I care to admit.
- Rain jacket: Especially in Kauai it drizzled nearly every afternoon.
- More coverups: I kept rotating the same one because it was so handy post-beach.
Things I Packed and Never Wore:
- Heels: Not once. My strappy sandals did the job for every dinner.
- Jeans: Too thick for the climate. I wish I had brought an extra pair of flowy pants instead.
- Heavy makeup: It melted off my face by lunch. Tinted sunscreen and a brow gel were my heroes.
Outfit Ideas That Look Great in Hawaii Photos
Let’s be honest half the reason we dress up on vacation is for the memories (and the Instagram posts). These combos photographed beautifully:
- White on the beach: Crisp and glowy in golden hour light.
- Bold florals in gardens or waterfalls: The colors pop without blending into the background.
- Coordinated couple outfits (not matchy-matchy): My partner wore neutrals while I rocked the prints it looked great in photos!
- Swimsuits + sarongs for poolside shots: Easy and natural.
Bonus tip: Early morning or sunset = best photo light. Avoid harsh midday sun unless you’re going for that full tropical brightness.
Final Thoughts: What You Wear in Hawaii Should Feel Like You
Packing for Hawaii doesn’t have to be complicated. Think light, breathable, and versatile and make sure you feel like yourself in whatever you bring. Whether you’re relaxing on the beach, hiking to waterfalls, or dancing under the stars, your outfits should feel fun and effortless.
Got a Hawaii trip coming up? Let me know what you’re packing or drop your outfit questions on Pinterest. I love swapping travel tips!
FAQs
What do people wear in Hawaii?
Most locals and travelers wear casual, breathable clothes. Think swimsuits, shorts, sundresses, and flip-flops.
Is it okay to wear Hawaiian prints in Hawaii?
Absolutely! Locals wear them too. Just avoid anything too costumey or stereotypical.
Do I need to dress up for dinner in Hawaii?
Not really. A nice sundress or a collared shirt is usually enough, even for nicer restaurants.
Should I pack a jacket for Hawaii?
A light layer for cooler evenings or rainy days is a good idea, especially on the islands with higher elevations.
