8 Stylish Ways to Wear Hawaiian & Floral Shirts (Modern Men’s Guide)

Hawaiian and floral shirts have gone through a major style revival. Once labeled as “corny,” these bold patterned shirts are now a trendy and versatile menswear staple. In this guide, inspired by Jeff from The Style O.G., you’ll learn how to wear Hawaiian and floral shirts in 8 modern, confident ways—without looking over-the-top.

The key principle is simple: when the shirt is bold, keep everything else clean and minimal.

General Styling Rule for Hawaiian Shirts

Hawaiian and floral shirts naturally draw attention. To keep your outfit balanced:

• Let the shirt be the focal point
• Stick to neutral pants and shoes
• Avoid loud accessories

This approach ensures your look feels intentional, stylish, and effortless.

1. Hawaiian Shirt with White Jeans

One of the easiest ways to start wearing a Hawaiian shirt is pairing it with white jeans. Choose a shirt with a base color you’re already comfortable with—black is a great option.

To tie the look together, match a color from the shirt with your footwear. For example, black loafers with a black Hawaiian shirt create a cohesive and polished summer daytime outfit.

2. Black Hawaiian Shirt with Black Jeans (Night Look)

For a sleek nighttime outfit, keep the bottom half monochromatic. Pair a black Hawaiian shirt with black jeans and black Chelsea boots.

This streamlined base allows the bold print to stand out while maintaining a sharp, modern silhouette—perfect for evening outings.

3. Pink Hawaiian Shirt with Light Wash Jeans

For a lighter summer evening look, pair a pink Hawaiian shirt with light wash jeans. This combination feels relaxed, fresh, and seasonally appropriate.

Complete the outfit with suede Chelsea boots to add texture and sophistication. Matching subtle blues from the shirt with the denim helps keep the look cohesive.

4. Hawaiian Shirt with Shorts and White Sneakers

In hot weather, swap jeans for shorts. Choose shorts that pick up a secondary color from your shirt for a coordinated look.

Finish with minimal all-white sneakers. This outfit is ideal for picnics, pool parties, beach days, and casual daytime outings.

5. Hawaiian Shirt with a Summer Suit

Hawaiian shirts can work surprisingly well with tailoring. Pair a bold Hawaiian shirt with a summer suit, such as a blue cotton or chino suit.

For example, a yellow Hawaiian shirt under a blue suit creates contrast while maintaining balance. Add casual sneakers, like caramel-colored ones, to keep the look relaxed and modern.

6. Hawaiian Shirt with Chambray Dress Pants

For a dressy yet fun outfit, combine your Hawaiian shirt with chambray dress pants. This pairing feels refined while still allowing personality to shine.

Finish with classic loafers for an elegant, smart-casual look suitable for dinners or creative professional settings.

7. Floral T-Shirt with Khaki Chinos

If button-up shirts feel too bold, start with a floral or wave-patterned t-shirt. Pair it with khaki chinos, one of the most versatile neutral pants.

Add all-white minimalist sneakers for a clean, relaxed, and polished everyday outfit.

8. Floral Polo Shirt with Dark Denim Jeans

A floral polo shirt is a subtle step up from a t-shirt and a toned-down alternative to a Hawaiian button-up. Pair it with dark denim jeans for structure and contrast.

Complete the look with white minimalist sneakers. This outfit works perfectly for weekends, casual dates, or movie nights.

Final Thoughts

Hawaiian and floral shirts are no longer outdated—they’re stylish, expressive, and incredibly versatile when worn correctly.

Remember:

• Let the shirt make the statement
• Keep the rest of your outfit simple
• Match subtle colors for balance

With these 8 outfit ideas, you can confidently wear Hawaiian and floral shirts in a modern, stylish, and effortless way.