Much like sequins and anything neon, the Hawaiian shirt is something you wear with the intention of having a good time and sharing a few laughs. But it’s no good if the laughs are made at your expense. And in the defense of a lot of men out there, it’s very easy to be mister-fun-loving guy with good intentions who doesn’t realise just how ridiculous he looks.

The key to avoiding this is choosing the right style of Hawaiian shirt, and to be able to differentiate between the good and bad, it’s important to understand the shirt’s history. To no one’s surprise, it hails from Hawaii, and while its exact origin is disputed, it’s clear that a patchwork of cultures contributed to the design we know today.

In the early 20th century, job-seekers from east Asia and the continental US flocked to Hawaii’s thriving plantations, and each culture contributed a distinctive design element: the Japanese brought the kabe crepe fabric used in the design of their kimonos; Americans brought the shirt collar; Filipinos brought the straight hem. The locals already had bright patterns locked down, but added these other elements to create an early version of the now iconic shirt. By the 1920s, it had become the unofficial uniform for plantation workers.

A decade later, a young Hawaiian store-owner called Ellery J. Chun spotted their mass-market potential and trademarked his version as the ‘Aloha shirt’. It blossomed into a must-have souvenir, then a mainland essential, after they appeared on the backs of A-list heartthrobs like Elvis Presley and Montgomery Clift in the 1950s.

As with any up, next came the down, as big box stores began producing cheap knock-offs that only a wacky uncle could love. But now the shirt is back, and designers have focused on making new versions of the shirt that are more Blue Hawaii, less Wayne Knight in Jurassic Park. That said, they’re still not a failsafe and nailing the look requires some thought.

Do

Embrace the camp collar. “Attitude is a key part of pulling this shirt off,” says our stylist, Alice Watt. “You don’t want a silhouette that buttons all the way up to the top – it conveys the wrong, stuffy message. A camp collar captures the same laid-back spirit and retro sensibility that makes the Hawaiian shirt so enticing.”

Don’t

Style it with other busy pieces. This will only overwhelm your outfit and draw attention away from your shirt. “The key is keeping the rest of your outfit simple – preferably colour-free and certainly print-free,” Alice says. Smart styles to pair with yours instead? A simple white tee, a pair of jeans or chinos, and some simple white kicks or boots.

Do

Know your brands. As we mentioned, there’s a lot of scratchy polyester out there, so it’s best to stick to brands who capture the authentic spirit of the shirt, while making it look fresh and new. “Percival and Reiss are two of my go-tos for great prints - they’re bold but not too gaudy,” Alice says. “The colours can be bright but in the right way; they don’t scream for attention.”

Don’t

Opt for a rigid fabric. “The more stiff the fabric, the more stuffy and forced the outfit will look,” Alice says. “It needs to ooze a nonchalant, care-free attitude, and choosing a looser fabric is the first way to master this.” Lightweight cotton, viscose, and linen blends are all great options, and as a bonus, they’ll keep you cool in Hawaii-style weather.

Do

Look for vintage-inspired prints that nod to the golden age of the shirt. Anything too loud or artificial will just look contrived, especially if the print is too on the nose – think hula dancers or pineapples. “Stick to abstract prints too,” says Alice. “Think florals that are more painterly than graphic. They’ll feel authentic and true to the original Hawaiian designs.”

Don’t

Go overboard on colour. The shirt should make a bright statement, but it shouldn’t give anyone a headache. “Stay away from neons,” Alice says. “You want to add spirit but still be taken seriously, and anything to ostentatious won’t do you any favors.” Luckily, there are plenty of colourful but tasteful options available – from pastels to punchy shades of yellow, red, and orange – that will lift your look without feeling kitschy.

Do

Put thought into how you style it. “There’s no one way to wear a Hawaiian shirt,” Alice says. “Because it’s typically made in a loose fabric, it can be worn tucked in, tucked down, and styled over a tee or vest – it really depends on the environment. It’s also possible to dress them up or down. Pair yours with some green chinos or tailored shorts and a pair of trainers, and you’re ready for a rooftop party. Style one with tailored trousers and boots, and you can even wear it in some casual office settings.”

Don’t

Forget to have fun with it. You’re in a bold print, so carry yourself with confidence and enjoy yourself. “At the end of the day, your attitude is the biggest indicator of whether you pull off something bold like the Hawaiian shirt,” Alice says. The idea is to evoke an easy, holiday feeling, even when you’re months away from your next trip to the beach.

Words: Allison Pavlick

Photography: Lola & Pani

Styling: Alice Watt

Styling assistant: Toby Standing

