Adam Sandler’s character Henry Roth in 50 First Dates captures the ultimate Hawaiian lifestyle—laid-back, colorful, and casual. His outfits are simple yet instantly recognizable, making them perfect for anyone who wants to channel that tropical charm.
1. Hawaiian Shirts
The key to Henry’s wardrobe is the Hawaiian shirt. He’s often seen wearing oversized, short-sleeve button-ups with bold floral patterns. In one of the most iconic scenes, he sports a light green shirt with white hibiscus prints. Look for bright colors and big prints to nail the vibe.
2. Basic T-Shirts
When he’s not in florals, Henry keeps it simple with solid color T-shirts—comfortable, casual, and perfect for layering with shorts or beachwear.
3. Cargo Shorts & Khaki Shorts
Henry pairs his shirts with loose cargo shorts or khaki shorts, keeping the look practical for his adventurous lifestyle in Hawaii. Neutral tones like beige or light brown work best.
4. Footwear – Island Style
For footwear, Henry sticks to sandals or casual sneakers. Comfort comes first—easy to slip on and perfect for the beach.
5. Accessories
Henry isn’t flashy with accessories, but a fishing cap or simple wristwatch would blend right in with his everyday island style.
Conclusion
To recreate Henry Roth’s 50 First Dates outfit, all you need are:
-
A Hawaiian floral shirt
-
A plain T-shirt
-
Cargo or khaki shorts
-
Casual sandals or sneakers
It’s an easy-going look that reflects the heart of the movie: relaxed, fun, and full of island charm. Perfect for summer, a beach vacation, or even a casual cosplay.
