The Hawaiian Shirt – or the ‘Aloha Shirt’ – is possibly one of the most polarising garments you’ll ever come across. This doesn’t make much sense, as the Hawaiian Shirt is one of the most cheerful items of clothing that one can own – the colour! The joyful palm leaves! Patterns of tiny hula dancers enjoying cocktails on the beach!
However, since its invention in the 1930s the Hawaiian Shirt has unfortunately come under scrutiny as being an indicator of the uncouth; an unfortunate way for loudmouth tourists to ‘blend in’ with the tropical location in which they’re visiting.
This is an unfair assessment, as Hawaiian Shirts can also indicate something else: coolness. A lot of cool people have worn Hawaiian Shirts. But who wore it best?
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Here are the contestants:
By current social standards, Hawkeye’s constant need to aggressively flirt with his co-workers – even when he is elbow-deep in a soldier that he is operating on – is definitely not cool. His commitment to swapping out his bloodstained scrubs for an off-duty Hawaiian Shirt is very cool, however. In this instance, the Hawaiian Shirt says, ‘I am a relaxed man who is currently not operating on anyone’. It is best worn while sipping on a cocktail served in a coconut.
This is obvious but it’s worth repeating: Romeo is super trendy. He’s so trendy that he’s allowed to write crappy poetry in a suit (???) at the beach (????????) and not even one person punches him in the face for it. Therefore, he is the perfect candidate to make a previously camp item seem ironic and hip. Romeo’s shirt was more of a fashion-y take on the traditional Hawaiian, with a nice Sacred Heart print in the middle. It also tended to billow open in a very romantic and dramatic way. Usually when the wind picks up a piece of your clothing, you feel very embarrassed. No-one felt embarrassed when it happens to him.
Hunter S Thompson was a real-life person – a fantastic ratbag, truly – who had a very specific dress code including big aviator sunglasses, a cowboy hat and snazzy ‘70s-style shirts. It’s unusual that people are able to a successful stick to a look for decades, but Hunter S Thompson did just that. In the movie version of his book Fear and Loathing in Las Vegas, he was played by his IRL friend Johnny Depp, who wore many printed shirts, including a black Hawaiian Shirt with acid yellow flowers on it. Disorienting, but effective all the same.
Ace Ventura pretty much only wears Hawaiian Shirts. His love of Hawaiian Shirts is meant to be indicative of his madness (‘Look at him! He can’t even wear the correct clothing!’) but in retrospect, Ace looks like some sort of hipster fashion icon. Could it be that the clothes of 1995 have circled back in fashion? Or has ironic fashion meant that we can’t actually tell what’s ‘good’ anymore? I’m not sure, but this pet detective sure has some snazzy cuts.
Hi is a goofball and an ex-convict who has no moral qualms about baby theft. His loud shirts – including a Hawaiian number which is red with big yellow flowers and yellow flecks – are meant to make us think that he is an obnoxious redneck. But Hi looks cool! He has a distinct look, which is an almost impossible thing to cultivate. There are actual reddit threads looking for the shirts that Nicholas Cage wears in this movie. (They’re not popular threads, but they’re still there.)
Was Tom Selleck responsible for bringing the Hawaiian Shirt back in the 1980s? It’s unclear. There are so many reasons why this fashion decision shouldn’t have worked – he tucked it in, seemingly only felt the need to button two of a possible six buttons, often paired the shirt with an ill-fitting baseball cap (Tom Selleck has a really big head). But inexplicably, this red shirt with squawking parrots on it, is cool. And he knows it.
Winner:
Romeo, duh.