25 Of The Most Fashionable Films For Some Sartorial Escapism

By Dan Ahwa
Preppy meets dark comedy in 1988 film 'Heathers'. Photo / Supplied

Films have long inspired the fashion world and beyond, but how do you narrow down the most stylish?

It's a tall order, and by no means does this list represent the best, but they are, in our opinion, a stylish bunch of films you can watch, rent, download, re-visit and escape into during this time of self-isolation.

Whether it's exploring modern-day consumerism (The Bling Ring, The Devil Wears Prada); coming of age and discovering your own identity (Kids, Call Me By Your Name) or historical explorations (Jackie, Barry Lyndon), these films offer plenty of escapism to enjoy from the comforts of home.

1. Heathers (1988)
"What's your damage?" this dark comedy is a riotous look at the lives of a high-school clique made up of four teenage girls all named Heather. Stylistically, the group dressed in tartan blazers, pleated miniskirts and loafers as they played croquet and ate pate. Winona Ryder's turn as Veronica Sawyer and Christian Bale's performance as the trench coat wearing bad boy Jason Dean are highlights; as is the red scrunchie worn by the leader of the gang Heather Chandler (Kim Walker), and later Heather Duke (Shannon Doherty).

2. Barry Lyndon (1975)
If you're a period film junkie, this is one of film director Stanley Kubrick's finest films, starring Marissa Berenson and Ryan O'Neal. Based on the 19th-century novel by William Thackeray, the sumptuous costumes and cinematography were purposefully lit in a way that mimicked an 18th-century oil painting. The frill collars, velvet coats and painted faces of the era capture the flounce and frippery of the day beautifully. Great soundtrack too.

3. Romeo & Juliet (1996)
Baz Luhrmann's update on the Shakespearean tragedy cleverly transplants 16th century Verona Italy to 90s modern-day Verona Beach, L.A  cue skate-inspired Hawaiian shirts and baggy jeans for the house of Montague; and Latin-inspired attire  flouncy shirts, fitted trousers and waistcoats for the Capulet crew. Juliet, played by a young Claire Danes, won bonus points for her 60s-inspired shift dress for her quick-fire wedding to Romeo, played by a floppy-haired Leonardo DiCaprio in one of the most memorable performances of his career.

4. Phantom Thread (2017)
In his last film ever, award-winning actor Daniel Day-Lewis plays the role of high-society fashion designer Reynolds Woodcock during the 1950s in London. Cue serious method acting and loads of elegant mid-century fashion the film's costume designer Mark Bridges won an Academy Award in 2017 for Best Costume Design. Beautifully filmed by Paul Thomas Anderson, it's the perfect escapist film to watch right now.

5. Jackie (2016)
Scoring an Academy Award nomination for her role as Jacqueline Kennedy, Natalie Portman makes a convincing turn as the young FLOTUS, complete with Jackie's unique elocution. The pink facsimile Christian Dior suit with pillbox hat on the day John F. Kennedy was assassinated makes a dramatic cameo in this autobiographical look at one of America's most stylish and intriguing women. The film's costume designer Madeleine Fontaine won several of her nominated costume categories that year.

6. Mahogany (1975)
A struggling fashion design student who rises to become a popular fashion designer in Rome. It's a campy melodrama made for Diana Ross, complete with extravagant costumes and wigs, a film that's provided Beyoncé with a blueprint for many of her own memorable style moments.

7. American Gigolo (1980)
A young Lauren Hutton and Richard Gere steal the show in this film that catapulted Italian designer Giorgio Armani into the spotlight. Richard's character Julian, a high-priced male escort, is an impeccably dressed man in Mr. Armani's relaxed suits and became the epitome of casual yuppie cool at the start of the 1980s.

50s upper-class style in 'Carol'. Photo / Supplied
50s upper-class style in 'Carol'. Photo / Supplied

8. Carol (2015)
Cate Blanchett's stunning performance as a love-struck socialite in New York during the 50s was enhanced by costumes designed by Sandy Powell, who looked to photographs in Vogue and Harper's Bazaar taken by the likes of Vivian Maier and Saul Leiter during 1952/1953 (the years this film is set in). Lush fabrics and elegant accessories for Cate established her role as the dominant figure in her tumultuous relationship with aspiring photographer and store clerk Therese Belivet played by Rooney Mara.

9. Annie Hall (1977)
Woody Allen might be problematic, however it's Diane Keaton's turn as the title character, a role written specifically for her, that we're interested in here. Referenced by myriad fashion designers since its release, the menswear-inspired looks have also informed Diane's personal approach to fashion over the years men's shirts, ties, trousers and this season's retro revival of a tidy waistcoat.

10. Clueless (1995)
Rich Cali girls epitomised the frivolous, ditzy mood of the 90s, from Donna Martin in Beverly Hills 90210 to Hilary Banks in The Fresh Prince of Bel-Air. But who can forget Alicia Silverstone as Cher Horowitz and her coterie of equally fashionable friends? Cher and best friend Dionne Davenport's tartan suits and OTT hats are highlights as were the guys dressed in oversized shirts and baggy chinos. The updated adaptation of Jane Austen's 1815 novel Emma spawned a slew of similar coming of age high-school films during the late 90s and early 2000s, and introduced the world to phrases and slang words with a valley girl twang. "Do you prefer fashion victim or ensembly challenged?" – Cher Horowitz.

11. Paris Texas (1984)
Stylish and the perfect armchair travel film to indulge in, this expansive look at the great American road trip journeys between Texas and California, and is a celebration of life on the open road in the US. Nastassja Kinski's pink sweater has become an iconic piece of film history too.

12. Catwalk (1993)
Right at the height of the supermodel era during the early 90s, this unique doco-film captures the dizzying days of the fashion world during a formative period. Look back at a time completely different from today's fashion reality, where models with individual characteristics dominated the industry including Naomi Campbell, Christy Turlington, Claudia Schiffer, Helena Christensen, Carla Bruni and Yasmin Le Bon. The film directed by Robert Leacock premiered in 1995, also included behind the scenes interviews with influential designers including Gianni Versace, Azzedine Alaia, John Galliano and Valentino. Watch the entire film above.

13. Call Me By Your Name (2017)
Luca Guadagnino's cinematic portrayal of romance between Armie Hammer's Oliver and Timothée Chalamet's Elio, is a lesson in early 80s yuppie fashion, specifically elements of 'Paniari' style from Italy  American sportswear mixed with a bourgeoisie European sensibility. Combining open collar shirts, Lacoste polo shirts, short shorts and canvas slip on-shoes, costume designer Giulia Piersanti painted a realistic portrayal of the ultimate languid and sensual summertime dressing. Bonus points for Elio's cool Talking Heads t-shirt. If not for a stylish watch, then perhaps the dulcet soundtrack featuring original music by Sufjan Stevens.

14. The Talented Mr. Ripley (1999)
An update on the 1960 psychological thriller Plein Soleil (Purple Noon) featuring Alain Delon, both films are an adaptation of Patricia Highsmith's 1955 novel, and this update directed by Anthony Minghella (The English Patient, The Reader) is easy on the eye, and a reminder that despite a perilous time for Italy right now, the landscapes and beauty of the country continue to inspire us in the hopes we'll make it back there one day soon. Award-winning costume designer Ann Roth dressed Gwyneth Paltrow, Jude Law, Matt Damon, Cate Blanchett, Phillip Seymour Hoffman and more in a variety of 50s holiday attire including full skirts and espadrilles, bowling shirts and Italian knitwear.

Faded glamour in 'Grey Gardens'. Photo / Supplied
Faded glamour in 'Grey Gardens'. Photo / Supplied

15. Grey Gardens (2009)
Starring Drew Barrymore as Edith Bouvier Beale aka Little Edie and her mother Edith Ewing Bouvier aka Big Edie played by Jessica Lange, this is the true-life story of Jackie Kennedy's first cousin and aunt's downward spiral into reclusiveness is a fascinating look at how two members of New York's high society found themselves withdrawing to their Long Island summer home of Grey Gardens, where the home eventually becomes a health hazard, overrun with cats and raccoons. Holed up in the estate, they make do with a haphazard wardrobe of vintage furs worn with cardigans as head wraps and worn our gowns, their faded glamour enhancing the tragedy of their situation.

16. The Royal Tenenbaums (2001)
Before there was Gucci through the lens of Alessandro Michele  there was this gem directed by Wes Anderson. Retro tracksuits, 70s inspired vintage looks are just some of the memorable outfits that made this film about the three gifted siblings and their trials and tribulations they face as adults. Gwyneth Paltrow as Margot Tennebaum with her vintage fur coat, Hermes bag, loafers and kohl-rimmed eyes is an endearing image of Sad Girls everywhere; while brother Chas shares his love of a red tracksuit with his two matching sons Ari and Uzi.

Latina style in 'Women on the Verge of a Nervous Breakdown'. Photo / Supplied
Latina style in 'Women on the Verge of a Nervous Breakdown'. Photo / Supplied

17. Women on the Verge of a Nervous Breakdown (1988)
This Spanish comedy has all the makings of a classic Pedro Almodovar film  women, drama and brightly saturated cinematography. Costume designer Jose Maria de Cossio was charged with bringing to life the ensemble female cast's powerful outfits  tomato red power skirt-suits and power shoulders prevalent during the late 80s, all set to a kitschy, primary coloured backdrop.

Coming of age in NYC during the early 90s in 'Kids'. Photo / Supplied
Coming of age in NYC during the early 90s in 'Kids'. Photo / Supplied

18. Kids (1995)
I remember the first time I watched this coming of age film and thinking how much I wanted to join a skate crew. Baggy denim jeans, crop tops and Converse All Star kicks became the uniform for many disenfranchised teens during this time. Directed by Larry Clark and written by Harmony Korine, the film's stylish legacy has influenced fashion since, including zine collaborations with JW Anderson in 2015, and anniversary collection with Supreme that same year. It was also the debut film for one of fashion's favourite individual style icons Chloe Sevigny.

19. I Am Love / Io Sono L'amore (2009)
Another stylish entry from Luca Guadignino, this stylishly shot film looks at the life of a powerful industrial bourgeoisie family in Milan, and the family dynamics and politics that come into play. What's even more striking is the way the family is dressed  sleek outfits for protagonist Emma Recchi played by Tilda Swinton, whose elegant and minimalist wardrobe created by Raf Simons during his tenure at Jil Sander, is a great example of sophisticated, Milanese chic.

20. In The Mood For Love (2000)
Wong Kar Wai's sumptuous look at unrequited love is one of the best films of all time. Inspiring our Hong Kong edition from 2018, the wardrobe of clinging qipao dresses in a vibrant array of prints and colours is a feast for the eyes set to the backdrop of old Hong Kong.

21. Funny Face (1957)
"Bonjour Pareeeee!" sang Audrey Hepburn on the Champ's Elysses. This seminal musical referenced eccentric magazine editor Diana Vreeland and saw the stylish transformation of Audrey as mousey sales assistant Jo Stockton into a bonafide modeling sensation. Camp, silly and fun, it's an interesting look at post-war mid-century silhouettes, and Fred Astaire's baggy chinos, blazer, and penny loafer outfit is another stylish highlight in this musical-comedy.

22. The Bling Ring (2013)
Sophia Coppola's film based on a 2010 Vanity Fair article by writer Nancy Jo Sales entitled 'The Suspects Wore Louboutins' is a TMZ fuelled escapade into the mid to late noughties era of peak celebrity obsession. The 'ring' of burglars who stole from the likes of Paris Hilton and Orlando Bloom, is also an interesting insight into noughties fashion  think including logo laden handbags and crystal-embellished tinted sunglasses popularised by young Hollywood at the time.

23. The Devil Wears Prada (2006)
If you're after a guilty pleasure, this satirical take on the cut-throat world of fashion magazines is a silly romp at the expense of all the fashion stereotypes you can think of. Based on Lauren Weisenberger's novel of the same name, Meryl Steep's turn as the ice-cold editor-in-chief of Runway magazine is worth watching (based on real-life Vogue editor-in-chief Anna Wintour). Oh and there's plenty of glossy fashion to take in too of course.

24. Coco Before Chanel (2009)
As one of the most iconic names in luxury fashion, the Chanel brand started by Coco Chanel has left a lasting legacy. This closer look at her life before she became a household name, is faithfully portrayed by French actress Audrey Tautou (Amelie) in the lead role, following Coco's life from orphan to a seamstress, ultimately creating and building the foundations for the storied fashion house of Chanel.

25. Pret-a-Porter (1994)
This satirical comedy pokes fun at the fashion world during the hedonistic early 90s and looks at disparate yet connected stores set to the backdrop of Paris Fashion Week. Keep a lookout for cameo appearances from designers, Sophia Loren in a big red hat and a hilarious performance by Kim Bassinger as the hapless fashion TV reporter Kitty Potter.

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