Jet-Set Style: What to Wear to the Airport in Winter

You’ve booked the flight, set your out-of-office message, and can almost taste the first mai tai. But there’s one question left before paradise: what do you wear to the airport when it’s winter at home and summer where you’re headed? When you’re trading rain boots for sandals, dressing for the airport in the winter is a balancing act—cozy enough for the cold, but breezy enough for your sunny arrival.

Comfort Comes in Layers

Start with travel-ready basics like a soft, colorful t-shirt or an IslandZone® performance shirt that’ll feel perfectly in place in paradise. Then, add pants that are comfy enough for a nap on the plane without looking like pajamas—like the bestselling Boracay® Island Chino, crafted with our signature comfort-stretch waistband.

For a little extra warmth (plus double the color options for your trip), throw on our Flipview Reversible Layer, and you’re ready for the first-class lounge.

For women, our Palm Voyage collection was made for moments like this. These chic separates are as soft as loungewear but elevated enough that they’re sure to become your gate-to-getaway go to.

Step Up Your Ease with Slip-On Shoes

For footwear, go where comfort meets convenience. We might not be taking off our shoes at the airport as often, but convertible Olukai® slip-on sneakers and loafers still make security a breeze (while looking effortlessly elevated). Plus, they’re as easy and comfortable as a pair of slippers, which is great for that long-haul flight to sunny shores.

Smart Packing for Smooth Getaways

Make organizing and unpacking a breeze with packing cubes to keep your daily outfits and swimwear separated for grab-and-go ease. A well-packed carry-on bag can be a life saver for long layovers and lost luggage. Make the most of the space you have with a few tropical vacation essentials on hand. tropical vacation essentials on hand.

• Mini toiletry kit with sunscreen
• Sunglasses and a hat or cap
• Noise-canceling headphones
• Reusable water bottle
• A light scarf or wrap
• A good book or a deck of cards

Packing tip: Rolling your clothes saves space and can help keep linen from wrinkling!

Arrive & Shine

With smart layers, easy accessories, and a relaxed attitude, you’ll be in vacation mode before the plane touches the tarmac. Ready to plan your trip? Check out a few of our location spotlights for a little inspiration!

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