Honolulu’s It Girl Spills The Secrets To Her Perfect Staycation

Where island life and the big city meet.

By Chanel Dror

Have you ever traveled to a new destination, and wondered who you might be if, in another life, you’d been born and raised there? Our trip to Oahu brought so many inspiring women into our lives, but above all, our time with Lindsey Higa of Pineapple Ice revealed the fashionable, fun-loving, cool island girl we want to be. Forget everything you thought you knew about life in Hawaii — Lindsey’s uniform is less wetsuit and more silk pj’s, and her idea of “hanging ten” is more like hanging with ten of her closest friends poolside.

We caught up with the fashion stylist living her best life staycationing in Waikiki’s Laylow Hotel — a colorful, design-forward place that pulls you in, and entices you to stay a while with its amazing food and drinks, photo-friendly interiors, and party ready spaces. It was the perfect backdrop for Lindsey to dish the best local designers, must-try cocktails, and so much more, making one thing clear: Pineapple Ice’s Honolulu is one that we want to live in.

hawaiian hotel breakfast

Pineapple Ice. What is it, what inspired it, and where does the name come from?

I got the name from my fave gourmet hot dog spot that served a pineapple slushy called Pineapple Ice. Pineapple Ice started as a fashion blog back in 2010. I I had just moved back home from San Francisco, and going back and forth from somewhere so tropical to a cold city by the bay, inspired me to share my new sense of style. These days, I do less blogging and way more wardrobe styling and content creation, so Pineapple Ice has become more of a portfolio for me!

We love the way you combine laid-back with fashion-forward pieces. How would you describe your personal style?

Because it’s always summer here, less is more! I wear a lot of basics, that sometimes have pops of color or a timeless print. Crop tops and wide leg pants have become my uniform!

lindsey higa of pineapple ice

We’ve come to know you for your amazing nail art. Has this always been a big part of your personal style?

I get my nails done at Salon Glitter Hawaii! I’ve been doing them every month for a couple years now. I love getting creative with my nail girl and coming up with so many designs and color combos!

the laylow hotel in waikiki lindsey higa of pineapple ice

Tell us about your love for vintage tees. What’s your go-to source?

Vintage tees are honestly the most comfortable piece you can wear. I love throwing it on over my swim suit on the way to the beach, wearing them with a fun printed pant, and even just around the house. It’s so versatile! I get most of my favorite vintage tees from No. 808 on the North Shore. My girlfriend Cappy (who owns the store) has a guy who finds her the coolest vintage Hawaiian pieces!

Let’s move on to Waikiki. How would you describe Oahu’s big city?

Waikiki is a very nostalgic place, with a lot of beautiful old hotels, and iconic surf spots. Although it’s always very crowded and full of tourists, it’s always fun to get down there and experience the hustle and bustle of it all. The Laylow Hotel is located in the heart of Waikiki. It’s one of Waikiki’s newest, but coolest boutique hotels! I’ve collaborated a ton with them by doing some social content, videos, and celebrated my last 2 birthdays there! It’s kind of my home away from home.

the laylow hotel in waikiki staycation style

poolside style at the laylow hotel hawaii is always a good idea

Do you take staycations at The Laylow often?

Staycations are a big thing here in Hawaii. Even though I live 15 minutes away, staying in Waikiki can make any local feel like their on vacation! We usually won’t leave the area (because what’s the point?), and will spend the whole weekend surfing, eating, and drinking at all our fave spots in Waikiki. The whole hotel is so photogenic and fun. The light at the seating area at the top of the escalator is always so on point, the view from the balcony down to the pool is always so picturesque, laying in the immersed pool chairs is so relaxing, and the bathroom lighting is beyond perfect!

lindsey higa of pineapple ice

How do you approach wardrobe styling? Is it very different from dressing yourself?

I started wardrobe styling on my own about 4 years ago, and it’s definitely been a huge learning experience for me! I’m very lucky to have traveled to beautiful places near and far, and have had the chance to work with some really amazing clients. Every job is always so exciting, challenging, and sometimes super stressful, but I love what I do!

shopping at the laylow hotel shop

the laylow hotel in waikiki

earrings collection

What’s your favorite way to spend time at The Laylow?

I love going to the Hideout at night and having dinner and drinks with friends. It’s always such a good energy up there, and is one of the few cool outdoor bars we have here on the island! When I staycation here for a night or two, my friends and I will take over a cabana and spend the day by the pool eating and drinking all our fave Laylow treats!

Your go-to staycations eats and drinks… go!

For breakfast/brunch, their Smoked Salmon Toast with potatoes instead of bread is my FAVORITE, and for lunch/dinner, I like the Coconut Curry Seafood Stew, and the Crispy Pork Belly for it’s delicious brussels sprouts! Their Slay Rosé is their in-house Rosé sangria, and is so refreshing for brunch or when you’re laying out by the pool!

lindsey higa of pineapple ice

tropical cocktail with orchid garnish

Lindsey’s favorite places to shop in Honolulu:

Lindsey’s favorite local brands:

lindsey higa of pineapple ice