Ultimate Hawaiian Holiday Packing List: What to Wear in Hawaii

While the mainland is bundling up in puffy coats and scarves this December and January, you’re trading snow for sand and trading boots for bare feet. There’s nothing quite like Christmas lights reflecting off the Pacific or ringing in the New Year with your toes in the water.

But here’s the truth: the #1 question every traveler Googles before a Hawaiian holiday is…

“What to wear in Hawaii?”

You want to look effortlessly chic, stay cool in 80°F weather, feel festive for holiday dinners, and still be ready for sunrise hikes or spontaneous mai tais at sunset.

Good news — we’ve got you covered (lightly, breezily, and in the most colorful way possible) with the ultimate Hawaiian holiday packing list built entirely around JAMS World’s iconic tropical prints and resort-ready silhouettes.

Let’s pack your suitcase with joy!

Your 10-Piece JAMS World Capsule Wardrobe for Hawaii (Mix-and-Match Magic)

The Day-to-Night Dress →Long Ruffle Dress - Garden Black
Perfect for Christmas brunch at Duke’s Waikiki or holiday dinner under the stars. Pair with sandals by day, add heels and statement earrings by night.
The Beach-to-Bar Maxi Dress →Anais Maxi Dress - Sea Flower
Flowy rayon that moves with the trade winds. Throw it on over your bikini and you’re instantly photo-ready.
The Lightweight Kimono Cover-Up →Flower Vibes - Kimono Your new best friend for sunrise yoga, poolside lounging, or adding a pop of print over any outfit.
The Perfect Beach Pants →Beach Pants - Palm Villa
Wide-leg, breathable rayon — ideal for exploring the Road to Hana or a casual holiday luau.
The Versatile Button-Up Rayon Shirt →Unisex Rayon Shirt in Crossroad
Great for everyone! Wear open as a lightweight jacket or buttoned for dinner.
The Go-Everywhere Pareo →Pareo - Fern Grotto
10+ ways to tie it: skirt, dress, scarf, beach blanket… the ultimate space-saver.
The Packable Sun Hat → Reversible Packable Bucket Hat
Crushes in your suitcase, pops back into shape, and saves your face from that strong Hawaiian sun.
The Cutest Tote Bag → Farmers Market Large Tote
Roomy enough for towels, sunscreen, and all the shaved ice you’ll eat.
The Cozy-Chic Travel Robe →Cliche Robe
Perfect for chilly flights and early-morning coffee on your lanai.
Bonus Festive Touch – Holiday Scrunchie
Because even your ponytail deserves to celebrate!

JAMS World Pairing Guide: Create 15+ Outfits with Just 10 Pieces

Midi Dress + Kimono + Hat → Effortless farmers market look
Beach Pants + Rayon Shirt (tied at waist) + Pareo as belt → Instant explorer vibe
Maxi Dress + Reversible Hat + Tote → Beach-to-holiday-party in seconds
Kimono over bikini + Pareo as skirt → Poolside goddess

Mix prints fearlessly — that’s the JAMS World way!

Quick Hawaiian Holiday Packing Checklist

2 JAMS World dresses
1 kimono
1 pair beach pants
1 rayon button-up shirt
1 pareo
Reversible sun hat
Large tote
Travel robe
Swimsuit (or three 😉)
Sandals + one dressy evening shoe
Light sweater (for airplane or windy nights)
Sunglasses & reef-safe sunscreen

What Real Travelers Are Saying About JAMS World

Don’t just take our word for it — here’s why thousands of happy customers keep coming back:

⭐️⭐️⭐️⭐️⭐️

“I love Jams World. Huge fan. This is their flagship store and it is the bees knees. You definitely want to check it out if you are in the area!!!”

— Andrew P. (Google Reviews)

⭐️⭐️⭐️⭐️⭐️

“I recently had to return a shirt which I ordered, which was too small. My fault. I can commend Tim for making the process so easy. Jams World has a great customer service group and I recommend buying shirts and other products from Jams World.”

— David B. (Google Reviews)

(Over 500 five-star reviews and counting — join the ohana!)