Matching Hawaiian Outfits for Couples & Families

Whether you're planning a tropical vacation, a Hawaiian wedding or a family gathering, matching a Hawaiian shirt and dress could be a great idea. We offer a variety of tropical prints, from hibiscus, plumerias and pineapples, in colors and sizes up to 8XL plus sizes in some prints for family reunions, Luaus or just to cruise along the beach. Click on the product you like to view all the matching items.

Showing 36 of 36 products

Honolulu Long Sleeve Hawaiian Wedding Shirt

$102.96 - $108.96

White

Short Sleeves Rayon Tropical Island Aloha Shirt

$62.96 - $68.96

Black
Aqua
Beige

Men's Honolulu White Hawaiian Aloha Shirt

$59.99 - $68.99

White

Relax Fit Polycotton Outrigger Hawaiian Shirt

$51.96 - $56.96

Sky Blue
Sage
Beige

Short Sleeves Side Border Prince Kuhio Aloha Shirt

Regular price $72.98

White

Cotton Poplin Niihau Men's Hawaiian Shirt

$47.98 - $57.98

Teal
Navy
Black

Signature Aloha Lei Men's Rayon Shirt

$62.98 - $68.98

Navy Blue

Men's Hibiscus Rayon Panel Island Shirt

$52.96 - $64.96

Navy
White
Black

Traveler Open Pointed Folded Collar Shirt

$59.99 - $65.99

Green

Men's Rayon Polynesia Aloha Shirt

Regular price $72.99

Rust

Polyester Spandex Polo Plantation Aloha Shirt

$75.96 - $81.96

White

Kimo Short Sleeve Men Rayon Tropical Aloha Shirt

$71.96 - $77.96

White

Island Day Folded Collar Hawaiian Rayon Shirt

$59.99 - $65.99

Black
Red

Retro Oasis Rayon Men's Hawaiian Shirt

$109.99 - $127.99

Rust
Cool Water
Moss

Retro Rayon Pineapples Men's Hawaiian Shirt

$109.99 - $127.99

Olive
Midnight
Morning

Short Sleeves Taro Aloha Resort Shirt

$85.66 - $100.66

Sky Blue
Red
Black

Short Sleeves Kailua Cotton Aloha Shirt

$51.65 - $56.65

Sky Blue
Navy
Maroon

Wailuku Men's Rayon Aloha Shirt

$85.09 - $95.09

Purple
Blue
Red
Gray

Lanai Pineapple Rayon Aloha Shirt

$69.97 - $72.97

Black
Blue
Sage

Hibiscus Relaxed Fit Hawaiian Shirt

$69.96 - $74.96

Aqua
Light Sky Blue
White

Short Sleeves Maui Pineapples Men's Aloha Shirt

$55.98 - $67.98

Cream
Navy

Short Sleeves Lanai Pineapple Cotton Men's Shirt

$49.96 - $58.96

Black
Red
Teal

Lanai Adventure Cotton Cool Hawaiian Shirt

$54.96 - $66.96

Dark Magenta
Coral
Ocean Blue

Short Sleeves Hibiscus Cotton Men's Aloha Shirt

Regular price $68.96

Navy
Red

Ukulele Royal Blue Hawaiian Men's Shirt

$78.96 - $90.96

Royal Blue

Birds of Paradise Rayon Men's Shirt

$69.94 - $79.99

Red
Black
White

Short Sleeves Pineapple Hawaiian Aloha Shirt

$75.96 - $99.96

Black

Big Island Hibiscus Cotton Men's Aloha Shirt

$55.96 - $73.96

White

Cotton Lanai Aloha Hawaiian Shirt

$52.66 - $70.66

Peach
Sky Blue
Navy
Red

Resort Moonlight Scenic Rayon Aloha Shirt

$51.98 - $56.98

Orange
Light Sky Blue

Hibiscus Cotton Men's Aloha Shirt

$55.96 - $61.96

Coral
Light Blue
Navy

Makapu Short Sleeves Aloha Rayon Shirt

$69.94 - $74.94

Corn Flower Blue

Hibiscus Men's Cotton Aloha Shirt

$54.96 - $72.96

Red
Royal Navy

Short Sleeves Ceres Rayon Men's Hawaiian Shirt

$52.99 - $57.99

Green

Rayon Wainapanapa Men's Hawaiian Shirt

$54.98 - $72.98

Navy
Red
White

Keilani Island Rayon Men Aloha Shirt

$54.96 - $66.96

Royal Blue
Black
Burgundy

Matching Hawaiian Outfits for Couples & Families

There’s something special about coordinating your look with the people you love—especially when it comes to tropical style. Matching Hawaiian outfits bring that island vibe anywhere you go, whether you’re headed to a beach vacation, a luau, or just want to add a little sunshine to your weekend plans. A Birds of Paradise Rayon Shirt and Dress. These prints and colors are fun, relaxed, and perfect for sharing that carefree spirit with your favorite people.

Couples’ Island Style

When couples match, it’s more than just a cute idea—it’s a way to show connection and playfulness. A men’s aloha shirt paired with a flowing floral dress makes a great combo for photos, parties, weddings or getaways. You don’t have to match perfectly; even coordinating patterns or colors can create a fun tropical balance. Check our Ukulele Royal Blue Hawaiian Matching Men's Shirt and Dress. Soft rayon fabrics and lightweight cotton keep things breezy, while classic island prints make sure you both stand out for all the right reasons.

Family Matching Looks

Why stop at couples? Families love matching island outfits too! Parents and kids can all share the same theme—bright palms, hibiscus blooms, or ocean waves. These looks make great vacation memories and are perfect for reunions or tropical-themed weddings celebrations. A Short Sleeves Ceres Rayon Men's Hawaiian Shirt and Dresses. Matching doesn’t mean identical—mix short and long dresses, button-up shirts, or even toddler rompers to keep everyone comfortable and stylish.

Easy, Relaxed, and Fun

The best part about these outfits is how easy they are to wear. They bring that laid-back island feeling to any setting while keeping you cool and coordinated. Whether you’re dressing for photos, travel, or simply want to brighten your day, matching Hawaiian outfits make every moment feel like a getaway.