Packing for my recent Hawaii vacation felt like a full-on Olympic event. I had to figure out how I would fill my suitcase with versatile clothes and accessories that could handle everything from beach days to waterfall hikes and sunset cocktails — all while being weary of the limited amount of space available in my suitcase. But I’m happy to say, I nailed it. These outfits took me from sandy toes to upscale dinners, ensuring I stayed comfy, cute, and ready for every excursion and activity.

I’ve visited Hawaii numerous times over the years, and I’ve fine-tuned my packing game even more with every trip I take. On my most recent one, I mixed up my arsenal of go-to pieces with items from my favorite retailers like Amazon, Nordstrom, and Revolve. If you’re like me and want to look stylish without overpacking, overspending, or stressing about mixing and matching, you’re in the right place. Whether you’re heading to Hawaii or just seeking fashion inspo for your next vacation, check out a breakdown of what I wore (and loved) on the trip I just took. The best part? Prices start at just $15.

Beach Outfits

Beach days are the heart of any Hawaiian getaway, and I made sure my looks matched the laid-back vibes. Whether lounging on the sands of Kaanapali Beach or snorkeling with sea turtles off the Maui coast, these pieces made it easy to transition from ocean dips to mai tais in style. I loved pairing my Dippin Daisy’s Rosa Rojas Chica Bikini Top and Lucca Bottoms with a few key accessories. That became my go to look for every beach, pool, and boat day. Keep reading to see what else I packed for my beach adventures.

MakeMeChic Crochet Pants

Crochet pants are a vacation essential. They instantly elevate any bikini and add a chic layer without sacrificing comfort. These have a soft, breathable fabric and an adjustable drawstring waist, making them perfect for the beach or poolside lounging. I went with the apricot color, but they come in black, white, and khaki too.

Gap Factory Big Poplin Shirt 

If I had to pick one versatile vacation piece, it’s the classic white button-up. A true beach-to-dinner chameleon, I wore mine as a cover-up over a bikini during the day and styled it with jeans for a casual evening look. Now 60 percent off, now’s the time to grab yours if you’re hunting for a deal.

Steve Madden Hazel Slide Sandals

Stylish sandals that feel like clouds? Yes, please. These Steve Madden slides were my beach day heroes. They’re neutral enough to pair with everything but still cute enough to stand out. Plus, they’re so comfortable, I practically lived in them all day long.

More Beach Outfit Ideas: 

Athleisure Outfits

With Hawaii’s endless trails and stunning hikes, I knew packing the right athleisure was a must. From waterfall hikes to morning yoga on the beach, my activewear had to be as versatile as my itinerary was. Matching workout sets, comfy sneakers, and a hands-free belt bag were the keys to staying stylish while exploring the island. Keep scrolling to find all the go-to athletic wear I brought.

Athleta Longline Piping Bra

While walking the Kapalua Coastal Trail, someone stopped me in my tracks to ask where my matching set was from. That’s how cute it looks. Athleta makes high-quality activewear without a steep price tag, and this bra is perfect for low-impact activities. The brand knows how to nail performance and style in one swoop, and this bra was no exception with the comfort, support, and style it offered. 

Athleta Salutation Stash High-rise Leggings

Pockets. Need I say more? These leggings not only have them, but they also offer the perfect mix of stretch and support. They’re lightweight but durable, making them perfect for my hike to Nakalele Blowhole. In them, I felt like a pro adventurer. One shopper even called them the “best workout and hiking pants ever.”

Hoka Arahi 7 Sneakers

If you haven’t jumped on the Hoka bandwagon yet, know that these sneakers were my hiking MVP, keeping my feet cushioned on every step of the trek. And after a day on the trails, they were still comfy enough to wander around Lahaina. They’re not just for Hawaii. I wear them to the gym, airport, and on strolls around Central Park, too.

Lululemon Everywhere Belt Bag

This belt bag was my daily companion. Whether I was hiking, shopping, or making impromptu beach stops, it kept my essentials close and my hands free. The water-resistant material was made for island life, and the anti-theft design gave me peace of mind. It easily fit everything I needed. My phone, wallet, room key, and sunglasses were all safe in one compact, stylish package.

More Athleisure Outfit Ideas: 

Fancy Dinner Outfits

There’s nothing quite like a Hawaiian sunset paired with a breezy dinner view. For chic oceanfront dinners and beachside cocktails, I aimed to put together outfits that were elevated, yet still captured the island’s casual vibe. Whether it was watching the sunset at Merriman’s or enjoying seafood at Honu, I packed pieces that could be dressed up or down for any dinner occasion, since the level of sophistication I was going for varied by night. 

PQ Swim Vanessa Strapless Fringe Dress

As soon as I spotted this dress, I knew it was meant to come on my trip to Hawaii. With its fringe hem and macrame overlay, it’s a true statement piece. I paired it with gold jewelry and heels for dinner, but it could easily double as a beach cover-up for daytime.

Dolce Vita Malabo Heels

The moment I slipped into these Dolce Vita Malabo Heels, they became my go-to footwear for all my dinner outfits. The perfect blend of comfort and chic, they were ideal for post-dinner strolls along the shore, pairing seamlessly with just about everything I packed.

Freie Liebe Straw Clutch Purse

A cute clutch is an evening essential, and I wore this straw piece nearly every evening. Spacious enough to fit all the essentials (aka my phone, lipstick, and mini sunscreen), and still small enough to not feel bulky, it’s super affordable.

More Fancy Dinner Outfit Ideas: 

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.