The Hawaiian shirt (or Aloha shirt as it’s also known) still proves to be popular with the man on the street, which is unfortunate, as he’s taken what should be super cool menswear item that’s reminiscent of affluent, optimistic post-war America with its tiki bars and exotica, and teamed it with a pair of bootcut jeans, a straw trilby and square toed Aldo shoes, to turn it into an object of mirth that’s fit only for BBQs and festivals. What a tragedy! In this post I’ll look at the history of the shirt and pick some current favourites that would grace any gentleman’s wardrobe.

How I wear my Debenhams Hawaiian shirt (toddler optional)

The shirt’s origins are interesting. It all started in the late 1800s, when Hawaiian based American plantation owners started enlisting workers from China, Korea and most significantly, Japan. These Japanese newcomers brought with them bright kimono fabrics, such as the yukata cloth, which is usually used in light robe construction, and patterns included bamboo and geometric shapes over white backgrounds. In the early 1930s, when Chinese-Hawaiian businessman Ellery Chun decided to produce a local style of shirt using yukata cloth with tropical designs, the Aloah Shirt was born.

Early Hawaiian shirt from 1935

Once mass production of the shirts began in Hawaii after WW2, they proved popular with beach-goers, but also provided off-duty servicemen with a upbeat alternative to their drab uniforms. They would return home with their novelty souvenirs and a craze was born for these “wearable postcards.” When Hollywood got hold of them in the early 50s (Montgomery Clift and Frank Sinatra wore them in From Here to Eternity), sales went through the roof and the whole world went crazy for all things tiki and exotica.

Monty turning up his collar in From Here to Eternity

I wear my Hawaiian shirts with a panama hat, a pair of chinos (with woven belt) white socks, and penny loafers. And yes, I always tuck them in unless they’re purposefully cut short to the waistband. Think 1950s American tourist and you’ll be set.

Anyway, here’s my pick of this season’s Hawaiian shirts:

Classic print and beautiful colours from Just Cavalli 

Button down vibrancy from J Crew 

No bamboo in sight, a subtle number from Oliver Spencer

Shimmering white and blue classic from Gitman Vintage 


Super 80s style car print from Saint Laurent

Long sleeves? Why not when Richard James comes up with this beauty! 

Pretty green from All Saints


Go all Scarface with this palm print number from Double Rainbouu