Three of the best from the films of the 90s.

Jude Law in the Talented Mr Ripley

The Cuban shirt is the comeback kid of menswear, having being around for some 300 years. Originating from – you guessed it – 18th century Cuba, it was first worn by workers labouring under the hot Havana sun. The Guayabera, to give its original name, had an open collar and straight hem that was designed to be worn untucked, along with four pockets on the front for carrying guavas (guayabas) back from the field.

By the 1950s the Cuban had made its way to America, losing its pockets and pintucks but gaining bold colours and Hawaiian prints. Despite being a favourite of stars like Elvis Presley, it soon lost its cool status and spent the next few decades in the hinterlands - except for, it seems, a brief blip in the late 1990s. While most of us were busy wearing shell suits and playing with yoyos, three of Hollywood's best leading men were foreshadowing the Cuban's 2018 comeback.

Romeo + Juliet

Leonardo DiCaprio in Romeo + Juliet

It’s easy to forget that long before he earned his title as Hollywood’s number one playboy, Leonardo DiCaprio was a baby-faced romantic doomed to eternal tragedy – on screen, at least. In 1996 and 1997, Leo scored a one-two punch with leading parts in Romeo + Juliet and Titanic, playing perhaps the most tragic of them all in the former. If you haven't seen Baz Luhrmann modern appropriation, it's the same familiar story: boy meets girl, girl fakes death to escape disproving father, boy drinks poison in anguish and dies. The Montagues and Capulets are recast as battling corporations, with a puppy-eyed Romeo driven to despair while sporting tumbling curtains and soft blue Hawaiian shirts. If you’re feeling similarly star-crossed, try wearing a Navy Cuban Shirt open over a White Raglan T-Shirt.

The Talented Mr Ripley

Talented Mr Ripley

Earlier this year Call Me By Your Name made a strong case for dropping everything, jetting to Italy and lounging in short-sleeved shirts-and even shorter shorts. But 19 years ago, it was the Talented Mr Ripley that set the benchmark for Italian summer style on celluloid. The film is set in Mongibello, a fictitious sun-kissed town where Jude Law and Gwyneth Paltrow idle their time wearing soft linen tailoring and scooting around on Vespas. That is until Matt Damon arrives and – spoilers – bashes Law’s head in on a rowboat. Murder aside, the 1999 film remains a masterclass in open collars, fluid fabrics and head-tot-toe neutral tones. To make like Mr Ripley, pair a White Jacquard Print Cuban Shirt with Oatmeal Linen Trousers and soft leather loafers.

Fear and Loathing in Las Vegas

Johnny Depp in Fear & Loathing in Las Vegas

According to Benicio Del Toro's Dr Gonzo, there are four things you’ll need when planning a drug-fuelled dash to Las Vegas: “A very fast car with no top. Cocaine. Tape recorder for special music. Acapulco shirts.” Of course, there’s only one of these things that we can endorse, and unsurprisingly, it’s the Acapulco shirt – a Mexican take on the Cuban. Throughout this 1998 psychoactive road trip, Johnny Depp’s Raoul Duke is seen in a number of bold printed shirts borrowed from Hunter S Thompson, the real-life Duke and author of the film’s source material. We’re especially keen on the yellow and black number above; which gets away with having a busy pattern thanks to the subdued colour palette, a trick we've employed with our own Mustard Hawaiian Print Cuban Shirt. Wear yours with Navy Casual Chino Trousers and clean white sneakers.

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Read more: How to wear a Grandad Shirt


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