50 Movies Every Fashion Lover Should Watch

Becca Endicott
50 Movies Every Fashion Lover Should Watch
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If you’re anything like us, you probably remember the first time you watched “Breakfast at Tiffany’s.” Specifically, you remember that you spent the whole movie swooning over Audrey Hepburn wearing amazing hats and dresses and hairstyles, and kind of didn’t pay attention to the plot at all. (Though it’s actually a really great, funny movie, and definitely worth a rewatch for the story alone.)

MORE: 20 Photos of Audrey Hepburn You’ve Never Seen

In any event, this is the iconic movie for amazing fashion, starting with Hubert de Givenchy’s amazing black sheath dress that has been immortalized as the original LBD, and ending with the black cigarette pants and cropped camel pullover that look as modern now as they did in 1961. That being said, “Tiffany’s” is just one fan-favorite among many amazingly chic movies that get our sartorial wheels spinning.

MORE: 50 Actors Who Turned Down Famous Movie and TV Roles

In honor of “Dior and I” premiering this week at the Tribeca Film Festival, here are 50 films on our must-watch list.

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"A Single Man" (2009) 

Tom Ford's directorial debut is, unsurprisingly, a stylish affair. It details a day in the life of George Falconer (Colin Firth), a gay university professor who is mourning the recent loss of his partner. Firth is solemn and dapper in tweeds, Julianne Moore is charmingly bouffant, and Nicholas Hoult is the perfect mod college boy.

"The African Queen" (1951)

Starring Katherine Hepburn and Humphrey Bogart, this Old Hollywood classic—set in Africa during WWI—is chock-full of romance, danger, and beguiling Edwardian frocks. 

"American Gigolo" (1980)

This film follows the exploits of a male escort named Julian, played by Richard Gere, who uses his profession to finance his passion for nice clothes, fast cars, and cocaine. After he is framed for a murder, his impeccable sense of style unravels along with his personal life.

"And God Created Woman" (1956)

Roger Vadim's romantic drama is the vehicle that launched Brigitte Bardot's career, and her image as a bombshell. In the movie, Bardot's character, Juliette, spends her days engaged in the complicated seduction of two brothers.  This movie is one-part tantalizing plot, two-parts French Riviera glamor.

"Atonement" (2007)

Based on Ian McEwan's novel of the same name, "Atonement" is an intense romantic drama set against the backdrop of WWII. It stars James McAvoyKeira Knightley, and Vanessa Redgraves, but the spotlight really shines on the sinuous, draped thirties frocks, and the tailored looks from the forties and fifties. 

"Annie Hall" (1977)

Woody Allen's famous rom-com follows the romantic plight of Alvy Singer (played by Allen) who falls for the eponymous ditsy, off-beat heroine, played by Diane Keaton. The film is equally famous for its myopic, New York-y wit, and Keaton's stylishly androgynous ensembles.

"Basic Instinct" (1992)

There's a lot going on in "Basic Instinct," a thriller about a woman who stalks and violently harasses an ex. It's definitely not a flick for the faint of heart, but it might be worth watching for Sharon Stone's immaculate white-on-white outfit alone.

"Belle Du Jour" (1967)

Starring French sexpot Catherine Deneuve, "Belle Du Jour" follows the entanglements of a bored housewife who takes up prostitution to alleviate her sexual ennui. Fashion-conscious viewers might find that they are equally enthralled by the exquisite Saint Laurent costuming. 

"Blow-Up" (1966)

"Blow-Up" is the kind of film that encapsulates and preserves a specific moment in cultural history, namely London during the Swinging Sixties. Directed by Michelangelo Antonioni, the movie stars many of the key fashion and film "It" girls of the time, included Vanessa Redgrave, Jane Birkin, and Veruschka.

"Bonnie and Clyde" (1967)

Warren Beatty and a louche, elegant Faye Dunaway star in this dramatazition of the infamous spree-killing duo. Dunaway's signature for the role was a mixture of historically-accurate thirties style, with a beatnik edge. 

"Breakfast at Tiffany's" (1961)

Originally, Marilyn Monroe was cast in the iconic role of Holly Golightly in the film adaptation of Truman Capote's novel. When Audrey Hepburn took on the role, she made it her own, imbuing the character with her own taste and her long-standing creative relationship with Hubert de Givenchy. 

"Breathless" (1960)

Jean-Luc Godard's New Wave classic is an elegant, black-and-white film that follows an aspiring American journalist living in Paris—played by Jean Seberg—as she gets drawn into the criminal activities of her rough-around-the-edges boyfriend. She wears cat-eye glasses, Breton stripes, and a full-skirted Dior dress.

"Cleopatra" (1963)

This opulent Hollywood homage to ancient Egypt is notorious for going a full 42 million dollars over budget. (FYI, that's the equivalent of 320 million today.) We're pretty sure that all of that extra money went to bedazzling Elizabeth Taylor until she was practically gold-plated, to grand effect.

"Clueless" (1995)

Cher Horowitz knows what she's talking about, Azzedine Alaia is definitely "like, a totally important designer." Starring Alicia Silverstone, this is the movie that taught us about "Monets," matchmaking, and the importance of a good plaid skirt suit. 

"Easy Rider" (1969)

Directed by Dennis Hopper, and starring Hopper and Peter Fonda, this movie is a snapshot of la vie boheme at the height of the Counter-Cultural Revolution. Hopper and Fonda are two hip cats, crossing country on impractically low-slung motorcycles, and meeting fringe-wearing hippie girls around every corner. Watch this if you wish you were at Woodstock. 

"8 1/2" (1963)

One of Federico Fellini's most famous works, "8 1/2" is a vaguely autobiographical project about the complexities of the creative process for an Italian movie director. It's also full of razor-sharp ensembles which are set off by the crisp, minimalist effect of black-and-white film. 

Edie Sedgewick, the most notorious of Andy Warhol's muses, is immortalized by Sienna Miller in this biopic about the life of the troubled young starlet. Edie favored black dancer's tights with miniskirts or tunics, and epitomized the mod ideals of fashion in New York at the time. 

"Flashdance" (1983)

Jennifer Beals stars as Alex Owens in this classic dance movie about a young woman who works during the day as a welder and at night as an exotic dancer in an effort to make it as a professional dancer. It is also responsibly for introducing the film-watching public to the ultra-casual, off-the-shoulder sweatshirt look. 

Photo: Topham Picturepoint/Press Association Images

"Funny Face" (1957)

It is pretty much impossible to divide Audrey Hepburn from high fashion, particularly in this musical comedy about a shy bookstore clerk (Hepburn) who is turned into a famous model by a top fashion photographer, played by Fred Astaire and inspired by Richard Avedon.

"Gone With The Wind" (1939)

This historical romance, based on the novel by Margaret Mitchell, is an ode to the romance of the deep South. The film stars Vivien Leigh and Clark Gable as star-crossed lovers, set against the back drop of the American Civil War. The movie is also famous for a scene in which the female protagonist, Scarlett O'Hara (Leigh) constructs an elegant gown out of an old pair of curtains.

"Gentlemen Prefer Blondes" (1953)

Marilyn Monroe stars in this picture about a pair of burlesque dancers struggling to find their way in the world. It's campy fun, and it's also the movie responsible for Monroe's infamous song, "Diamonds Are A Girl's Best Friend."

"The Great Gatsby" (1974)

Yes, we know, Baz Luhrmann just redid this movie and it was beautiful and spectacular. But we happen to harbor a soft spot for the original 1974 adaptation of F. Scott Fitzgerald's novel. It stars a waif-like Mia Farrow as Daisy, while Gatsby is portrayed by the golden boy of the era, Robert Redford. Together, they make a perfect Roaring Twenties couple.

"Heathers" (1988)

Who doesn't love "Heathers?" It's a deliciously kitschy flick about murderously cliquey high school girls. Starring Winona RyderChristian Slater, and hundreds of shoulder pads, this is a deeply satisfying slice of late eighties style. 

"Kids" (1995)

This is one for the artsy kids. Harmony Korine, indie darling auteur of the nineties, wrote this movie about the urban dissatisfaction of a group of teenagers growing up in New York City. This was the debut performance for Rosario Dawson and Chloe Sevigny, and is an excellent showcase of nineties alt style.


"La Dolce Vita" (1960)

Another Fellini classic, "La Dolce Vita" is a romantic dramedy about a tabloid reporter looking for love among the glitz and glitter of the social upper class in Rome. Fellini has talked about the densely ornamented costumes of this movie as a metaphor for excess masking internal despair. Whatever the philosophical root, the costumes are gorgeous.

"Marie Antoinette" (2006)

Kirsten Dunst plays France's most iconic (and unfortunate) queen in this cartoonishly stylized Sofia Coppola vehicle. The movie focuses on the frivolity and indulgences of the naive young queen—known for her impractically elaborate hair and low-cut gowns—as France is poised on the brink of popular revolution.

"Mystery Train" (1989)

Jim Jarmusch's tripartite film follows the mishaps of three groups of international tourists traveling through Memphis, Tennessee and staying at the same hotel. Sartorially, this movie is notable for the awkwardly vivid uniforms of the hotel employee, and for the "rocker kid" fashion idealized by the film's protagonists.

"Out of Africa" (1985)

Meryl Streep and Robert Redford star in this adaptation of a novel by the same name, as a pair of Danish friends who form a marriage of convenience and move to East Africa in 1913. Streep, as Karen, demonstrates a raw-boned elegance befitting a woman on the colonial frontier.

"Pierrot Le Fou" (1965)

Another classic from Jean-Luc Godard, this film stars Jean-Paul Belmondo and model Anna Karina in an uncommonly colorful variation on the French New Wave style. Karina is a beautiful ingenue on the French Riviera who gets swept up in the intrigue surrounding Belmondo's dubious past.

"Pretty In Pink" (1986)

This is a teenage romantic comedy from John Hughes about a teenage girl from the wrong side of the tracks (Molly Ringwald) who is crushing hard on a preppy rich boy at school (Andrew McCarthy.) The movie derives its title from Ringwald's iconic off-the-shoulder pink dress.

"Pretty Woman" (1990)

"Pretty Woman" is essentially the inverse of Richard Gere's role in "American Gigolo." Here, he plays out a Pygmalion plot-line as a rich guy who decides to transform a prostitute (Julia Roberts) into a perfect facsimile of high-class woman. All of the fashion in this movie is awesome, from Roberts' thigh high boots to her gorgeous opera outfit.

"Purple Noon" (1960)

Here's another French movie to add to your Must-Watch list. It follows an American in Italy, on a mission to carouse on his friend's dime. You may be more familiar with "The Talented Mr. Ripley," but this original version has the effortless Medditeranean style that characterizes so many films made in France in the sixties. 

"Quadrophenia" (1979)

Loosely based on a rock opera by The Who, this movie follows the life of a disillusioned British mod and his pals, who are all about fighting the establishment. As you would imagine, fitted suits and skinny ties are in high supply. 

"Rear Window" (1954)

One of Alfred Hitchcock's most famous thrillers, this film stars Jimmy Stewart and Grace Kelly as a couple who become embroiled in a murder that occurred in a nearby apartment block after Stewart witnesses the crime. As with most Hitchcock films, the attention to detail (especially the fashion!) is incredible.

"Reality Bites" (1994)

Starring Winona Ryder, this movie was Ben Stiller's directorial debut, and captures the lives of a handful of recent college grads as they try to make their way in the world. They're grungry, proto-hipster types, so the emphasis on floral dresses and creeper mary-janes is intense.

"Reservoir Dogs" (1992)

Quentin Tarantino's film about the events surrounding a botched diamond heist is known for its dark humor and gratuitous violence. It should also be known for the impeccable, matching tailored suits that the criminals wear.

"Romeo + Juliet" (1996)

Shakespeare's tragic love story is reimagined here by the fertile mind of Baz Luhrmann. Featuring young, winsome versions of Leondardo DiCaprio and Claire Danes as the namesake couple, Luhrmann's movie is a frenetic, highly-stylized modern interpretation of the story as a battle between rival organized crime families. The clothes, particularly in the costume party scene pictured above, are equally extravagant.

"The Royal Tenenbaums" (2001)

As previously notedWes Anderson movies tend to be pretty fashion-forward. Of all of his movies, probably the most stylish is "The Royal Tenenbaums," which is characterized by the static, iconic styles worn by each of the main characters, like Margot Tenenbaum's (Gwyneth Paltrow) striped dress and fur coat, or Richie Tenenbaum's (Luke Wilson) tennis headband and unkempt facial hair.

"Rosemary's Baby" (1968)

This movie is known for including Mia Farrow's dramatic pixie cut. She goes from a meek bob to an edgy crop over the course of the movie, as her pregnancy progresses and the inevitably violent climax of the film approaches.

"Shaft" (1971)

This action/film noir flick follows a private eye named John Shaft as he tracks the missing daughter of a client through New York City. The lead character is played by Richard Roundtree, and wears leather trenchcoats, turtlenecks, and some stellar muttonchops.

"Stranger Than Paradise" (1984)

Another Jim Jarmusch picture, this movie is an absurdist story about three aimless young people traveling around the country. It culminates with the three taking roadtrip to Florida. The film is deliberately old-school. It's shot in black-and-white, and the two men wear fedoras and sweaters, while the woman is usually in a minimalist ensemble of sunglasses, turtleneck, and slacks.

"Taxi Driver" (1976)

This Martin Scorsese movie stars Robert De Niro, and a very young Jodie Foster as a fourteen-year old prostitute. This film is notorious for its Lolita-esque portrayal of the Foster's character, Iris, and also highlights the emergence of punk fashion following the Vietnam War.

"The Virgin Suicides" (1999)

Starring Kirsten Dunst, this movie follows the lives of the five beautiful Lisbon sisters, who all commit (or attempt) suicide within a single year. Watched closely by a posse of infatuated neighborhood boysled by Josh Hartnett, this movie captures the idea of the unattainable female ideal.

"The Devil Wear Prada" (2006)

One of fashion's favorite movies, the film adaptation of Lauren Weisberger's novel is a fictionalized account of Weisberger's own experience working as the assistant to the Editor-In-Chief at a major fashion magazine (widely acknowledged to be Vogue). The movie stars Anne Hathaway and Meryl Streep.

"The Dreamers" (2003)

Directed by Bernardo Bertolucci, this film covers the disturbing, incestuous relationship between an American college student and a pair of French siblings. Despite the subject matter, the film is visually beautifully, and full of Eva Green wearing fantastic clothes.

"Thelma & Louise" (1991)

Geena Davis and Susan Sarandon star in this buddy movie about two women on the run from the law after the kill a would-be rapist. They drive across country in a desperate bid to make it Mexico, rocking high-waisted jeans, cropped tees, and sidearms the whole way. 

"The Talented Mr. Ripley" (1999)

This reinterpretation of "Purple Noon" deserves its own spot on the list, because it stars Matt DamonCate BlanchettGwyneth Paltrow, and Jude Law as glamorous young people dabbling in the high life in Rome, led by the sociopathic and eventually murderous Tom Ripley (Damon.)

"Trainspotting" (1996)

Ewan McGregor's breakout role in this independent film brings a whole new meaning to the term "heroin chic." The film follows a group of heroin addicts living around Edinburgh in the late 1980's. Despite the depressing subject matter, there's a definite stylish edge to the stripped-down aesthetic of the movie.

"Vertigo" (1958)

Another Hitchcock masterpiece, Vertigo is a twisted story of crime and love starring Jimmy Stewart and Kim Novak. Arguably the best part of the movie is that we get two different sartorial sides of Novak—the highly-polished side that characterizes her as a socialite, and the bookish, slighyl mousier side that she displays in her real life.

"Zoolander" (2001)

Last but not least, "Zoolander." Starring Ben Stiller as the title character, this comedy is an incredibly silly parody of the fashion industry, as told through the eyes of the "really, really, really good-looking" model Derek Zoolander. Though the movie is definitely intended as a major exaggeration of the fashion world, it is, nonetheless, a very amusing way to look at fashion.

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