The Best Boutiques in Kailua: A Guide to Shopping Paradise (Without Breaking the Bank)
Listen mama, I get it. You’re here for that perfect family vacation, and between wrangling kids and making sure nobody drowns, you still want to find some cute stuff. Lucky for you, I’ve done the legwork (and spent way too much money) figuring out the best boutiques in Kailua.
Before we dive into my favorite shopping spots, can we talk about capturing these memories? There’s something magical about Kailua’s powdery white sand and turquoise water that makes every family photo look like a postcard. As a family photographer here on Oahu, I’ve learned that the best boutiques in Kailua often provide the perfect outfits for beach sessions. Check out my work at alisonbellphotographer.com – because trust me, you’ll want professional photos of your crew looking adorable in your new finds!
Table of Contents
Why Kailua Shopping is Different Than Mainland Boutiques
Here’s the thing about shopping in Kailua – it’s not your typical mall experience. These boutiques are curated by people who actually live here, which means everything feels authentic and beachy without being cheesy tourist trap material. Plus, the vibe is so chill that even my most shopping-resistant kid doesn’t complain.
And can we talk about supporting local designers? The best boutiques in Kailua carry clothes and accessories actually designed and made in Hawaii – not that mass-produced “Made in China, printed with a palm tree” stuff you’ll find crowding the racks in Waikiki. When you shop these local boutiques, you’re supporting real island artists and designers who pour their hearts (and understanding of island life) into every piece.
Your money stays in the community, and you get clothes that actually reflect Hawaiian culture instead of some mainland company’s idea of what “tropical” should look like. Trust me, there’s a huge difference between a locally designed sundress that moves with the trade winds and some synthetic disaster that’ll have you sweating through your sunscreen.
The best boutiques in Kailua are concentrated in a walkable area, which means you can park once and hit multiple stores. Genius, right?
Want Oahu travel tips from a MOM in your inbox?
Just drop address below!
Twin Island Surf Co – Where Surf Culture Meets Style
They carry everything from rash guards to board shorts, plus those perfect “island casual” pieces that somehow make you look put-together even when you’re covered in sand.
Twin Island Surf Co is hands down one of the best boutiques in Kailua for families. Here’s why I’m obsessed:
- Real surf gear that works – Not some mainland knockoff
- Kids’ sections that don’t suck – My boys actually found stuff they wanted to wear
- Local artist collaborations – You’re supporting island creators
- Reasonable prices – Your husband won’t give you the stink eye
- Address: 131 Hekili St #105, Kailua, HI 96734
- Hours: Daily 9:00 AM – 8:00 PM
Lauren Roth Art – Gallery Shopping at its Finest
Lauren Roth Art isn’t your typical boutique, but it’s definitely one of the best boutiques in Kailua for unique finds. This local artist creates the most gorgeous ocean-inspired pieces:
- Original paintings – Actual Kailua views you can take home
- Prints and cards – Perfect for gifts or your own walls
- Jewelry inspired by the ocean – Subtle island vibes
- Art classes available – Fun activity for older kids
- Address: 44 Kainehe St, Kailua, HI 96734
- Hours: Tuesday-Saturday 10:00 AM – 5:00 PM, Sunday 10:00 AM – 4:00 PM
Pro mom tip: Lauren’s work captures the exact blues and greens of Kailua Bay. I may have bought three pieces for my own house because I’m weak.
Golden Trip – Vintage Vibes with Modern Appeal
Golden Trip is one of those best boutiques in Kailua that makes vintage feel fresh and fun:
- Curated vintage clothing – No digging through musty piles
- Modern accessories – Sunglasses, bags, jewelry
- Instagram-worthy pieces – Your feed will thank you
- Reasonable prices – Vintage without the vintage price tag
- Address: 315 Uluniu St, Kailua, HI 96734
- Hours: Daily 10:00 AM – 6:00 PM
The owner has an amazing eye for pieces that feel both retro and current. Perfect for moms who want to look effortlessly cool.
The Salty Babe – Beach Life Essentials
If you’re looking for the best boutiques in Kailua for beach lifestyle gear, The Salty Babe is your spot:
- Sustainable swimwear – Cute AND environmentally conscious
- Beach cover-ups that actually cover up – Fellow moms, you know
- Kids’ swim gear – Including those impossible-to-find toddler rash guards
- Beach bags and accessories – Function meets style
- Address: 131 Hekili St, Kailua, HI 96734
- Hours: Daily 9:00 AM – 7:00 PM
Everything here screams “effortless beach goddess” which is exactly what we’re going for, right?
Please Come Again – Quirky Gifts and Island Finds
Please Come Again is one of the best boutiques in Kailua for those “I can’t believe I found this” moments:
- Unique home goods – Island-made ceramics and art
- Quirky gifts – Perfect for friends back home
- Local snacks and treats – Stock up on island favorites
- Handmade jewelry – One-of-a-kind pieces
- Address: 42 Oneawa St, Kailua, HI 96734
- Hours: Daily 10:00 AM – 6:00 PM
The name says it all – you’ll definitely want to come back. I’ve never left empty-handed.
Kono’s for Milkshakes – Not a Boutique, But Essential
Okay, Kono’s isn’t technically a boutique, but it’s absolutely essential shopping in Kailua fuel. These milkshakes are legendary:
- 19 flavors of thick, creamy perfection
- Perfect post-shopping reward – Bribe your kids with this
- Local institution – You can’t visit without trying one
- Worth the drive – Trust me on this
- Address: 41-865 Kalanianaole Hwy, Waimanalo, HI 96795
- Hours: Monday-Saturday 6:00 AM – 2:00 PM, Sunday 6:00 AM – 12:00 PM
Pro tip: The haupia (coconut) milkshake tastes like Hawaii in a cup.
Easy Kailua Shopping Map
Most of the best boutiques in Kailua are within walking distance of each other along Kailua Road and Hekili Street. Park at Kalapawai Market (grab snacks while you’re there) and walk to everything. The whole shopping area is maybe six blocks, making it perfect for families.
Quick Walking Route:
- Start at Twin Island Surf Co and The Salty Babe (same building)
- Walk to Golden Trip (2 blocks)
- Hit Please Come Again (1 block)
- Visit Lauren Roth Art (3 blocks)
- End at Kalapawai for snacks
Mom-to-Mom Shopping Tips for Kailua Boutiques
- Timing is Everything: Hit the best boutiques in Kailua early (10-11 AM) or late afternoon (after 4 PM). Midday is when tour buses arrive.
- Bring Cash: Some smaller boutiques prefer cash, and you’ll avoid those pesky card fees.
- Pack Light: You’ll be walking and carrying purchases. Bring a beach bag or small tote.
- Let Kids Explore: Most shop owners are super welcoming to families. Don’t stress about perfect behavior.
Making Shopping Work with Family Photos
Here’s where my photographer brain kicks in – the best boutiques in Kailua are goldmines for coordinating family outfits. Think flowing dresses, linen shirts, and those perfectly faded swim shorts that look effortless but photograph beautifully.
The natural lighting in these shops is also incredible for candid shots of your family browsing together. Some of my favorite family photos happen during these spontaneous shopping moments – kids trying on hats, parents laughing over silly souvenirs.
If you’re planning a family photo session during your Kailua visit, I’d love to help you capture these memories professionally. The combination of gorgeous boutique finds and Kailua’s stunning backdrop makes for photos you’ll treasure forever. Check out my family sessions at alisonbellphotographer.com and let’s create something amazing together!
Your Kailua Shopping Game Plan
The best boutiques in Kailua offer something you won’t find anywhere else – that perfect blend of island authenticity and tourist-friendly accessibility. Whether you’re hunting for the perfect beach cover-up or a unique piece of art to remember your trip, these shops deliver.
My advice? Give yourself at least half a day for shopping in Kailua. Grab coffee, let the kids pick out a few things, and soak up that small-town island vibe. These aren’t just stores – they’re part of what makes Kailua special.
And remember, some of the best family memories happen during these unplanned shopping adventures. The best boutiques in Kailua aren’t just about buying stuff – they’re about experiencing the real Hawaii, one perfectly curated shop at a time.
Ready to capture your family’s Kailua adventure? I specialize in relaxed, natural family photography that tells your story. Let’s chat about creating beautiful memories during your visit – alisonbellphotographer.com
More to Things To Do on Oahu with Kids
- The Best Boutiques in Kailua: A Guide to Shopping In O’ahu
- Family Friendly Veteran’s Day Events 2025 On Oahu, Hawaii
- Oahu July 4 Fireworks 2025: Where to Watch the Best Shows With Your Family
- The Ultimate Things To Do In Kailua Hawaii: Perfect Day After Sunrise Beach Photos
- Oahu Easter Events 2025: Spectacular Egg Hunts & Festivals
- The Best Turtle Bay Photography for Families Oahu, Hawaii
I'm a USMC spouse, South Carolina native, recovering homeschool mama of a 4 boy circus. They've taught me the most important facet of family photography: KEEP IT FUN!
Alison's Process
contact Alison
