How to Style Hawaiian Shirts for Men: A Modern Guide
Hawaiian shirts, once reserved for beach vacations and dad wardrobes, are having a serious style comeback. With their bold patterns, breezy fabric, and laid-back vibe, they’re now a go-to choice for men looking to add a little personality to their everyday outfits. But how do you wear a Hawaiian shirt without looking like you’ve just stepped off a cruise ship?
Let’s break it down with styling tips that’ll help you wear Hawaiian shirts with confidence, whether you’re heading to a weekend brunch, a casual office, or even a summer date.
1. Choose the Right Fit
The first step to styling a Hawaiian shirt well? Fit is everything.
Go for a tailored or relaxed fit — not oversized
Look for shirts that sit neatly on your shoulders, offer a bit of room in the chest, and fall just below your waist. Oversized Hawaiian shirts can look sloppy unless you’re intentionally going for a streetwear vibe.
Slim guys? Try slightly looser fits.
This helps add shape and dimension to your look without drowning your frame.
Bigger build? Stick to structured styles.
Avoid ultra-thin, clingy fabrics. A slightly stiffer material with a clean drape can make you look more put together.
2. Keep It Simple with Solids
If you’re new to Hawaiian shirts, start with classic floral prints in just one or two colors. A navy shirt with white hibiscus flowers? Easy. A black shirt with green palms? Timeless.
- Pair these with neutral bottoms:
- Khaki or beige chinos
- Light denim jeans
- White or navy shorts
Let the shirt do the talking and keep everything else low-key.
3. Smart-Casual Vibes: Dress It Up
Yes, you can dress up a Hawaiian shirt.
Layer under a blazer
For a cool summer evening, try wearing a subtle-print Hawaiian shirt under a lightweight linen blazer. Pair with dark slim-fit jeans or tailored trousers and loafers for a balanced, modern look.
Tuck it in
A tucked-in Hawaiian shirt with chinos and a leather belt can instantly elevate your style. Add clean white sneakers or loafers to finish the look.
This combo is perfect for:
- Casual Fridays at the office
- Outdoor parties
- Dinner dates
4. Beach-Ready Looks: Keep It Chill
Heading to the beach or a summer BBQ? Go all-in on the relaxed vibes.
Pair with shorts
Stick to solid-colored shorts — black, tan, navy, or white work best. Add flip-flops or espadrilles, and maybe a straw hat if you’re feeling extra summery.
Go unbuttoned with a tee
Want an effortless layered look? Throw your Hawaiian shirt open over a plain white or black T-shirt. It adds dimension without much effort.
5. Streetwear Edge: Bold and Trendy
If you’re into fashion-forward styles, Hawaiian shirts can totally fit into your streetwear rotation.
Here’s how:
- Choose shirts with loud, retro prints
- Go oversized with dropped shoulders
- Pair with cropped trousers, joggers, or even wide-leg jeans
- Add sneakers like Vans, Converse, or Jordans
- Throw on a bucket hat or chain for extra flair
- Think of this as Hawaiian shirt meets urban cool.
6. Monochrome or Muted Prints for Minimalists
Not into loud colors or flashy prints? Good news — there are minimalist Hawaiian shirts out there too.
Opt for designs in monochrome shades like black and white, navy and grey, or earthy tones. Pair them with slim jeans or tailored pants for a sleek, understated style.
7. Footwear Matters
Don’t forget about the shoes — they can make or break your look.
Here are a few go-to options:
- White sneakers: clean, modern, and work with almost any Hawaiian shirt combo
- Loafers or boat shoes: great for smart-casual looks
- Flip-flops or slides: ideal for beachwear or lounging
- Espadrilles: give off a laid-back Mediterranean vibe
Match your footwear to your outfit’s vibe — casual or dressed up — and keep it clean and coordinated.
8. Accessorize Wisely
Keep accessories simple and natural. Think:
- Woven bracelets
- Straw hats or fedoras
- Aviator sunglasses
- Canvas totes or leather backpacks
Avoid heavy or flashy jewelry. Hawaiian shirts already bring attention — let them shine.
9. Seasonal Considerations
Hawaiian shirts are mostly a spring/summer staple, but you can stretch them into fall with a little layering.
Try this:
- Throw on a denim or lightweight bomber jacket
- Layer over a long-sleeve thermal shirt
- Pair with black jeans and boots for a rugged-meets-relaxed look
- Just avoid wearing Hawaiian prints in cold-weather climates where they feel out of place.
10. Know the Occasion
Finally, match your Hawaiian shirt style to the occasion.
| Occasion | Style Tip |
|---|---|
| Beach/BBQ | Unbuttoned with shorts, sandals |
| Brunch/Date | Tucked in with chinos, loafers |
| Office Casual | Subtle print under blazer, tailored pants |
| Streetwear | Bold oversized shirt, joggers, sneakers |
| Vacation Look | Loud prints, relaxed shorts, espadrilles |
Final Thoughts
Hawaiian shirts aren’t just novelty items anymore — they’re a versatile, stylish addition to any man’s wardrobe. Whether you’re after laid-back summer vibes or a smart-casual statement, there’s a way to make them work for you.
The key is balance. Let the shirt take center stage and keep the rest of your outfit clean and coordinated. Once you find a style that suits your taste and body type, you’ll discover just how easy (and fun) Hawaiian shirts are to wear.
So go ahead — embrace the bold print. Your wardrobe will thank you.
Keep exploring:
- Why Is a T-Shirt Called a T-Shirt?
- Are Hoodies Still in Style in 2025?
- Can Women Wear Hawaiian Shirts?
