How to Wear Hawaiian & Floral Shirts: 8 Outfit Ideas That Actually Work

In this video, Jeff from The Style O.G. breaks down how to wear Hawaiian and floral shirts in a modern, confident way. Once considered “corny,” the Hawaiian shirt has made a strong comeback and is now a stylish, versatile staple when worn correctly.

Below are the key styling principles and outfit combinations he demonstrates.

Core Styling Rule

When wearing a bold, printed Hawaiian or floral shirt, keep everything else in your outfit clean, neutral, and minimal.
The shirt should be the focal point—your pants, shoes, and accessories should support it, not compete with it.

8 Hawaiian Shirt Outfit Ideas

1. Hawaiian Shirt + White Jeans (Easy Starter Look)

Choose a Hawaiian shirt with a base color you’re already comfortable wearing—black is a great option. Pair it with white jeans for a clean, classic summer daytime outfit.

Style tip: Match one color from the shirt to your footwear or accessories (e.g., black loafers with a black-based shirt) to create cohesion.

2. Black Hawaiian Shirt + Black Jeans (Nighttime Look)

Turn the same black Hawaiian shirt into an evening outfit by pairing it with black jeans and black Chelsea boots.
The monochromatic bottom half keeps the look sleek and balanced while letting the shirt stand out.

3. Pink Hawaiian Shirt + Light Wash Jeans

For a lighter summer evening vibe, pair a pink Hawaiian shirt with light wash denim and suede Chelsea boots.
Matching the blue tones in the shirt with the jeans creates a subtle color connection.

4. Hawaiian Shirt + Shorts + White Sneakers

Perfect for hot weather, pool parties, or picnics.
Pair your Hawaiian shirt with shorts and minimal all-white sneakers for a relaxed, effortless daytime outfit.

5. Hawaiian Shirt with a Summer Suit

For a bold but stylish statement, wear a Hawaiian shirt under a summer suit.
Example: a yellow Hawaiian shirt with a blue cotton chinos suit, finished with caramel-colored sneakers.
This look balances playful energy with modern tailoring.

6. Hawaiian Shirt + Chambray Dress Pants

For a dressy yet fun option, pair a Hawaiian shirt with chambray dress pants and classic loafers.
This combination feels cool, elevated, and fashion-forward without being overly formal.

7. Floral T-Shirt + Khaki Chinos

If button-ups aren’t your style, a floral t-shirt works just as well.
Pair it with khaki chinos, one of the most versatile and neutral pants options, making it easy to style any bold print.

8. Floral Polo Shirt + Dark Denim

For a more subtle approach, choose a floral polo shirt.
Pair it with dark denim jeans and clean white sneakers—a great look for weekends or casual dates that still feels polished.

Final Styling Advice

Hawaiian and floral shirts are all about confidence and balance. Keep the rest of your outfit simple, let the print speak, and choose combinations that fit your lifestyle and comfort level.

As Jeff emphasizes, there’s no single “right” way to wear a Hawaiian shirt—what matters most is how you make it your own.