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The Coolest Film Wardrobes

The Coolest Film Wardrobes

Words by Axel Metz

From Nineties favourites to modern classics, we pick the best of Hollywood’s wardrobes.

It’s easy to forget the role of a costume designer on a film set. Amongst the bright lights and big personalities of Hollywood actors and directors, the humble wardrobe selector falls some way down the pecking order when it comes to considering the best films of our time. With this list, we pay tribute to the work of the fashion teams that made – and in some cases, saved – some of cinema’s most iconic hits.  

Boyz n the Hood (1991)

From Cuba Gooding Jr.’s outrageous yellow shirt to Ice Cube’s iconic, ever-present Compton snapback, John Singleton’s Boyz n the Hood deserves recognition for its role in the boom of L.A. street style throughout the Nineties. Realising the popularity of N.W.A. at the time, Singleton reportedly called Ice Cube and “told him to bring all his N.W.A. paraphernalia to the set” in an attempt to add an authenticity to the film’s wardrobe. It worked – black snapbacks and oversized shirts spoke to the trends of the moment in Southern California, and forced a striking contrast to the more vibrant aesthetics of Tre and Ricky, whose lighter sweatshirts and Tommy Hilfiger-esque double denim represented a move away from traditional ‘gangster’ styling for a more experimental look befitting the hip, urban areas of Los Angeles.

Bad Boys (1995)

Michael Bay’s 1995 action comedy became iconic for many reasons; the electric chemistry between stars Will Smith and Martin Lawrence, the outrageous shoot-out sequences which established the director as Hollywood’s number one pyromaniac and, perhaps most importantly, its proof that the double shoulder holster can be an everyday wearable. Marcus and Mike shoot their way through the streets of Miami with about as much grace as Michael Bay himself – but they don’t half look cool doing it.

Romeo and Juliet (1996)

The wardrobe to end all film wardrobes, Baz Luhrmann’s adaptation of Shakespeare’s most famous play drew plaudits for its awe-inspiring fashion as much as it did for its faithful recreation of the Bard’s dialogue. Leonardo DiCaprio’s now-iconic Hawaiian shirt was emblematic of the laid-back Montague clan, expertly juxtaposed against the more serious (and very Italian) leather and black velvet styling of John Leguizamo’s Capulets. Clare Danes’ Prada-designed, angel-winged white dress drew starry-eyed wonder from party-going women of the Nineties, while DiCaprio’s armour-plated knight costume became the Halloween outfit of choice for any man hoping to snag his own Juliet. There’s a reason posters of the film adorn the bedroom walls of teenage girls and boys alike – and it’s probably not the one Shakespeare had hoped for when he put pen to paper 400 years ago.  

The Talented Mr. Ripley (1999)

Despite being made just before the turn-of-the-century, Anthony Minghella’s psychological thriller is in fact set in the 1950s, the decade that introduced Italian design into menswear. Jude Law’s Dickie Greenleaf struts around in linen trousers, loafers and knitted polos à la the French Riviera, while Matt Damon’s Tom Ripley appears plucked from the pages of a Ralph Lauren catalogue in his pastel-coloured oxford shirts and Oliver Peoples spectacles. For the preppy, Ivy league-cum-Oxbridge style savant, The Talented Mr. Ripley is a fashion bible.

American Psycho (2000)

Given that much of Bret Easton Ellis’ 1991 novel is dedicated to the meticulous description of Brooks Brothers suits, Armani ties and bespoke card holders, it’s no surprise that Mary Harron’s film adaptation places equal emphasis on the sartorial elegance of its lead character, Patrick Bateman. Pin-stripe blazers, burgundy suspenders and Rolex watches populate the excessive lifestyles of Wall Street’s yuppie elite, and it’s hard not to fall for Bateman’s killer (sorry…) style.

Pearl Harbour (2001)

Michael Bay’s recreation of the 1941 attack on Pearl Harbour is terrible. The script is trite, the romance is clichéd and the onslaught of visual effects wears thin one hour into its three-hour run-time. Luckily, the film’s saving grace comes in the form of its uber-fashionable era. Polka dot dresses, cigarette trousers and pomade-laden haircuts keep Pearl Harbour from being an entirely unwatchable experience, and make you wish (violence notwithstanding) you could spend a day roaming the bay of Honolulu in the 1940s. Even Josh Harntett’s grease-covered army shirt looks cool.

Call Me by Your Name (2017)

What film style list would be complete without 2017’s award-winning foray into young love? Luca Guadagnino’s coming-of-age drama bowled over critics and audiences alike with its moving script, beautiful locations and, of course, the mainstream arrival of one Timothée Chalamet – but it’s the film’s laid-back summer style that still inspires wardrobes to this day. Baggy Ralph Lauren shirts and short (short) shorts of neutral hues are the order of the day in 1980s Northern Italy, partnered with classic Ray-Ban wayfarers and rusty bicycles for good measure.  

Once Upon a Time in Hollywood (2019)

Fashion is, by necessity, a crucial part of Quentin Tarantino’s tribute to the final moments of Hollywood’s golden age. Set in 1969 Los Angeles, an ensemble cast of Leonardo DiCaprio, Brad Pitt and Margot Robbie don all the hallmarks of Seventies style; brown leather, oversized eyewear, sideburns, mini-skirts, suede boots and lot’s (and lot’s) of denim. Robbie’s Chanel-esque outfit as Sharon Tate broke the internet and sparked a slew of Pinterest boards celebrating the era, while Brad Pitt’s Cliff Booth single-handedly made aviators cool again. Even if Tarantino’s dark humour isn’t to your taste, we defy you to walk away from Once Upon a Time in Hollywood without a wistful nostalgia for the Seventies.

Still after more fashion inspiration? Read our style lessons to learn from Call Me by Your Name star Timothée Chalamet.

The Urban Journal

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