Here's how to style a Hawaiian shirt without looking like your dad.

By Monica Mendal
May 01, 2019
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
Claudio Lavenia/Getty Images

When a Hawaiian shirt comes to mind, a visual of your dad at a summer barbeque with a larger-than-life grin on his face likely follows. Jimmy Buffett is probably playing in the background, too. For some time, the only particularly “cool” reference of the Hawaiian shirt was a throwback to Tom Selleck in Magnum, P.I. (as I’m often reminded by my brother in his defense of wearing one). But no matter what sort of kitschy references a short-sleeved, tropical-printed top resurfaces for you, it unequivocally evokes a carefree spirit — the Hawaiian shirt is the ultimate symbol of vacation.

It’s no surprise that the style has undergone a sort of renaissance over the years. For many seasons, menswear designers have introduced modern versions of the trend, and now even womenswear designers have started catching on, making a strong case for everyone to try out this warm-weather staple.

Related: 16 Stylish Caftan Dresses for the Easiest Vacation Outfits Ever

Brands like Tombolo and Double Rainbouu are reimagining the classic Hawaiian top, thoughtfully considering print and fit for both men and women. Tombolo has even collaborated with artists to give the shirts an authentic edge.

Below, we show you how to wear the best Hawaiian shirts of the season.

Safari Chic

Courtesy of Gimaguas/Net-A-Porter/Moda Operandi/Montunas/Matches Fashion/Barneys/Sephora

(clockwise from top left)

Gimaguas jungle hat,, $62
Double Rainbouu shirt,, $195
Timeless Pearly anklet,, $185
Oséree swimsuit,, $265
Tom Ford lip blush,, $55
Montunas bag,, $554
ATP Atelier sandals,, $350
JW Anderson shorts,, $412
Lowercase sunglasses,, $350

Flower Power

Courtesy of Net-A-Porter/Matches Fashion/Lorna Murray/Norte/fwrd

(clockwise from top left)

Lorna Murray hat,, $85
Dries Van Noten shirt,, $630
19-69 perfume in Capri,, $195
Clé de Peau Beauté SPF 30 sunscreen,, $80
Emily Levine bag,, $145
Solid & Striped swimsuit top,, $80,
Solid & Striped swimsuit bottom,, $75
Norte necklace,, $55
Ancient Greek Sandals wedges,, $165
Dries Van Noten shorts,, $670

Casual Wear

Courtesy of Tombolo Company/J.Crew/Moda Operani/Net-A-Porter/Matches Fashion/Everlane

(clockwise from top left)

Tombolo shirt,, $128
Frame shorts,, $180
Beck Jewels earrings,, $295
Sea Star Beachwear bag,, $48
Benoît Missolin headband,, $135
Everlane flats,, $115

Tropical Disco

Courtesy of Net-A-Porter/APM/Shopbop/Sephora

(clockwise from top left)

Playa hair oil,, $38
Blouse shirt,, $269
Kosas lipstick in Stardust,, $28
APM Monaco earrings,, $154
Paco Rabanne bag,, $600
Jennifer Behr scrunchie,, $98
Alexander Wang shorts,, $200
Zimmermann sandals,, $495

Rainbow Beach

Courtesy of Net-A-Porter/Gabriel For Sach

(clockwise from top left)

Lack of Color hat,, $135
Le Specs sunglasses,, $129
Faithfull the Brand pants,, $190
Les Girls Les Boys swimsuit,, $97
YSL nail polish,, $28
AMIRI shirt,, $790
Gabriel for Sach bag,, $147