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Top 10 Most Stylish Movies

VO: Lisa Yang WRITTEN BY: Savannah Sher
These costume departments were working overtime. For this list, we’re looking at our favorite films that feature memorable fashions, rather than films that were shot in a stylish way. Our list includes “Clueless,” “The Great Gatsby,” “The Devil Wears Prada,” “Grease,” “Sex and the City,” and more! Join MsMojo as we count down our picks for the Top 10 Most Stylish Movies.

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Top 10 Most Stylish Movies

These costume departments were working overtime. Welcome to MsMojo and today we're counting down our picks for the Top 10 Most Stylish Movies.

For this list, we’re looking at our favorite films that feature memorable fashions, rather than films that were shot in a stylish way.

#10: “Sex and the City” (2008)

The “Sex and the City” TV show was known for its memorable fashions and while this movie wasn’t necessarily globally beloved by fans, costume designer Patricia Field displayed some of her best work to date. From the scene of the girls trying on outfits in Carrie’s closet to her Vogue bridal sequence, the entire movie is a visual treat for fashion lovers. The styles are brighter, bolder, and more over-the-top than they were in the original series, but still stay true to each individual character’s personal style.

#9: “Annie Hall” (1977)

Not many movies can claim to have pioneered an entire fashion movement, but Woody Allen’s classic romantic comedy “Annie Hall” did just that. The titular character’s menswear inspired look was never intended to spark a new style, but it inspired a generation of women nonetheless. Diane Keaton’s iconic androgynous look was a blend of Ralph Lauren’s deft hand (he lent many pieces to the film before he was a household name) and costume stylist Ruth Morley. But the fun fact you might not know is that many of the pieces used in the film actually belonged to the leading actress herself.

#8: “Atonement” (2007)

While many entries on our list today are for movies where there are many memorable outfits, this film is notable for a single gown. This 2007 period piece, based on the novel by Ian McEwan, offers stunning World War II era sets and gorgeous cinematography, but for the most part, it isn’t exactly considered a fashion flick. The one exception is the emerald green gown that Keira Knightley's character wears during one of the film’s key scenes. In fact, this dress was voted by readers of UK’s InStyle Magazine as the single best movie costume of all time, beating out many other cinema classics.

#7: “Grease” (1978)

The 1950s setting of “Grease” makes for a visual smorgasbord of pastel colors, poodle skirts, and bomber jackets. The initial contrast between good-girl Sandy and her edgy new friends, the Pink Ladies, means there’s something for everyone in this feel-good musical. Whether you like Sandy’s demure hoop skirts or Rizzo’s more seductive pencil skirts, this film will make you long for a bygone era. Then of course there’s the outfit that Sandy wears in the final scene when she’s trying to impress Danny. We’ve all tried to emulate that sleek all-black outfit and devil-may-care attitude.

#6: “La Dolce Vita” (1960)

Federico Fellini brought Italian glamour to the masses in 1960 with his groundbreaking film, “La Dolce Vita.” This movie is stylish in more ways than one, with the art direction being a major consideration for every frame. The costume designers clearly put significant effort into both the men’s and women’s outfits for the film. Of course there’s the curve-hugging dress worn for the iconic fountain scene, but did you know that the character of Marcello Rubini may have originated the idea of wearing sunglasses at night?

#5: “Clueless” (1995)

Cher and her friends’ Valley Girl style sparked many memorable 90s trends. From the plethora of plaid to the slinky slip dresses, this movie was filled to the brim with incredible fad-worthy pieces. What girl didn’t fantasize about having a computer system to help her pick an outfit in the morning? Somehow, even over 20 years after its release, the Beverly Hills teen styles on display in “Clueless” still feel fresh and totally wearable. The 90s are coming back and we’re not complaining.

#4: “The Devil Wears Prada” (2006)

In a film all about the cutthroat industry of fashion journalism, there were of course going to be a bevy of beautiful outfits to drool over. At Vogue (oops, we mean Runway), fashion is a competition and new hire Andy learns quickly that her cerulean sweaters and practical skirts are not going to fly. Anne Hathaway is queen of the makeover scene and her looks after her transformation are totally stunning. Meryl Streep as editor-in-chief Miranda Priestly inspired amped-up office dressing in viewers and there were no exceptions in the rest of the cast.

#3: “The Great Gatsby” (2013)

There have been two notable film adaptations of F. Scott Fitzgerald's classic work “The Great Gatsby” and while both featured incredible fashions, Baz Luhrmann's 2013 version perfectly exemplifies the excess of the period. Academy Award winning costume director Catherine Martin (who is married to Luhrmann) interpreted the Jazz Age fashions and modernized them slightly for contemporary audiences. Miuccia Prada designed many of the costumes for extras, as well as for Carey Mulligan’s Daisy Buchanan. The flapper dresses, extravagant beading, jeweled headpieces, and tons of sparkle made for memorable looks that will be beloved for generations to come.

#2: “A Single Man” (2009)

It comes as no surprise that a movie directed by esteemed menswear designer Tom Ford would be a feast for the eyes. The film focuses on the life of a gay university professor, portrayed by English actor Colin Firth. His character’s style is most in focus, with every detail meticulously and flawlessly executed. For men looking for some fashion inspiration in cinema, they need look no further than “A Single Man.” Julianne Moore’s modish 1960s look (and especially her flawless cat eye makeup) is also something to behold.

Before we unveil our top pick, here are a few honorable mentions.

“The Seven Year Itch” (1955)

“The Royal Tenenbaums” (2001)

“Breathless” (1960)

#1: “Breakfast at Tiffany's” (1961)

When you think of iconic movie style, there’s no doubt that Audrey Hepburn’s classic look in this 1961 film comes to mind. The entire movie is filled with beautiful costumes. But of course, the most memorable is the black gown, opera length gloves, and pearls that Holly Golightly wore while eating a pastry outside of Tiffany’s. Three copies of the original dress were made and when one sold at auction, it brought in close to a million dollars. It wasn’t necessarily the first Little Black Dress to appear on film, but it’s undoubtedly one that made the look an essential one.

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