tropical date night

What to Wear on an Aloha Date Night

Date nights are a wonderful way to bond and have fun with your significant other. Maybe you’ve been married for decades or maybe you’re just getting started. Wherever you are on this spectrum, one of the biggest decisions you have to make is what to wear. If you live in a coastal area where you can see the ocean, we suggest a tropical date night.

Casual Date

Aloha wear is inherently a casual look so if your date night involves a casual restaurant or location, picking the right look should be pretty easy. For men, you can't go wrong a with a good pair of blue jeans and a Hawaiian shirt that’s in the middle of the boldness and colorful spectrum like the Magnum Orchid shirt. And for women, a simple short or mid-length dress or blue jeans and a floral top will provide just the right amount of tropical relaxed flair.

Star Orchid (Magnum PI) Hawaiian shirt with blue jeans

short floral spaghetti Hawaiian dress at sunset

casual Aloha shirt and Hawaiian dress

Fun & Active Date

We’re also fans of doing something fun like going to a boardwalk amusement park, riding a hot air balloon, or going to one of those places where you cook your own food. Since places like these are more active, you’ll want something that allows you to move about freely. For the guys, we recommend shorts or jeans and an Aloha shirt that skews toward the bolder and more colorful end of the spectrum like a retro silk shirt. And for the women, you can’t go wrong with shorts and jeans with a floral top. If the weather is calm and warm, a fun dress is a great look. 

Breeze Red Retro Hawaiian shirt with khaki shorts


women's Hawaiian shirt and dress

Bold red Hawaiian shirt at a cook your own food restaurant

Hawaiian shirt on a hot air balloon ride (Photo courtesy of @NapaValleyBalloons)

Nice Place Date

Maybe your plans for a date night include a nice dinner with a view or checking out a new wine bar. You’ll want to dress up a bit while still maintaining an Aloha vibe. One of the easiest ways for guys to upgrade their look is to switch from blue jeans to black jeans or slacks while wearing a rayon Hawaiian shirt with darker tones. Wearing a nice watch also adds a touch of class. And for women, a long Hawaiian dress or a dress from Angels by the Sea will create a more upscale resort look. Compliment the look further with your favorite pair of earrings and bracelets.

Midnight Bamboo black Hawaiian shirt with black jeans

Angels by the Sea black dress and a long Bamboo Paradise Hawaiian dress

date night dress and shirt