The Most Stylish Movies in History

Forget about the actors or the story! Baz Lurhmann's new version of The Great Gatsby looks absolutely fabulous, and we can chalk that up in part to the gorgeous costume designs and set decorations, which reminds us of the last time that F. Scott Fitzgerald's classic American novel hit the big screen with Robert Redford and Mia Farrow starred in the 1974 version. Both are part of a legacy of stylish movies that have graced the big screen.
Gone With the Wind (1939)

Producer David O. Selznick spared no expense in bringing Margaret Mitchell's beloved bestseller to the big screen. The film may have recreated the Civil War-era South on Hollywood backlots -- when "Atlanta" burned, so did the giant wall from 1933's King Kong -- but audiences were swept away by the drama and romance, thanks in no measure to the exacting, colorful costumes and lavish, Academy Award-winning art direction.
Singin' in the Rain (1952)

The terrific songs and dazzling dancing by Gene Kelly, Donald O'Connor and Debbie Reynolds were the undoubted stars of the show, but the movie's appeal also hinges on nostalgia for the early days of filmmaking. The silent era is gently and lovingly spoofed, chiefly through eye-popping sets and a succession of costumes that both send up and celebrate the excesses of the 1920s.
Some Like It Hot (1959)

Director Billy Wilder mined the criminal underworld of the Roaring Twenties for laughs, forcing musicians Tony Curtis and Jack Lemmon to dress up to look like ladies (sorta) while hiding in plain sight in Florida from gangster George Raft (who doesn't love his spats!). Aided and abetted by the incomparable Marilyn Monroe, the film won an Academy Award for best costume design and a nomination for its art deco-inspired art direction.
Cleopatra (1963)

Even though it made more money at the box office than any other movie that year, it took years to turn a profit because it also cost more than any other movie! It's hard to complain about the Academy Award-winning art direction -- bear in mind that the sets had to be built twice in different locations due to production delays -- or the beautiful, extravagant, Oscar-winning costumes, including 65 for Elizabeth Taylor alone.
Bonnie and Clyde (1967)

The exciting French New Wave of filmmaking came to America with this groundbreaking and influential picture, which established Warren Beatty as a potent creative force and Faye Dunaway as a leading fashion icon of the day. Theodora Van Runkle designed the costumes, most notably dressing Dunaway in long skirts, a beret, and a fashionably short jacket. Combined with her hairstyle, the stylish look became a trend-setting sensation.
The Godfather (1972)

Admittedly, most people may not necessarily think of (arguably) one of the greatest movies of all time as a particularly stylish movie. But consider the rich period detail, immersing the viewer in the post-World War II era of New York. And the impeccable men's suits remain fashionable, no matter how bloody and bullet-ridden they get; and greatly influenced contemporary audiences (including real-life gangsters) to adapt similar styles.
The Sting (1973)

The anachronistic use of ragtime music -- Marvin Hamlisch adapting Scott Joplin -- helped distinguish this jaunty 1930s-set comic drama. Befitting a movie in which grifters Robert Redford and Paul Newman attempt to con big-time gangster Robert Shaw, every criminal looks remarkably well-dressed and well-to-do and, well, swell. Naturally enough, the film walked away with Academy Awards for costume design and art direction.
Chinatown (1974)

From seedy hotels to opulent mansions, writer Robert Towne and director Roman Polanski captured 1937 Los Angeles in a naturalistic manner, taking advantage of many period locations that remained essentially unchanged decades later. That results in a very lived-in look for the movie, with a strong aroma of corruption and decadence; nonetheless, the decay has an undeniably glamorous appeal, accented by the Oscar-winning art direction and costumes.
Murder on the Orient Express (1974)

It's freezing cold outside when the legendary train known as the Orient Express puffs to a stop in 1935, but inside the plush cars, it's sure stuffy. But none of the wealthy passengers would dream of NOT dressing for dinner, and if you owned clothing as elegant as they did -- Tony Walton's fussy yet never too busy costumes are to die for -- you'd always dress for dinner too, despite a murder on board.
Barry Lyndon (1975)

Renowned for his exacting attention to detail, Stanley Kubrick strove to reimagine the 18th century period movie, insisting, for example, that scenes featuring candlelit action actually be lit only with, yes, candles -- a nearly-impossible technical challenge, but one solved with unforgettable, breathtaking beauty. And when the light is good, the landscapes shimmer and you can practically feel the fabric of the costumes, designed by Milena Canonero.
The Fortune (1975)

Mike Nichols set his screwball comedy in the 1920s, but that doesn't quite absolve it of its confused sexual politics, nor of its uncertain performances by the would-be dream pairing of Jack Nicholson and Warren Beatty. After all these years, though, our memories remain fixed on the marvelous, striking outfits designed by Anthea Sylbert and the remarkably rich production design by Richard Sylbert.
Out of Africa (1985)

Frankly, before Sydney Pollack made this lushly appointed movie set in Kenya, it's unlikely that anyone thought of Karen Blixen (who wrote books using the pen name Isak Dinesen) as a romantic icon. That's the magic of the movies, though, especially when Karen is played by Meryl Streep and she's paired romantically with Robert Redford over a period of decades, and they're both dressed by the marvelous Milena Canonero.
The Untouchables (1987)

Law enforcement officers have never looked as good as they did in this glorious adaptation of Eliot Ness' book, set in Prohibition Era Chicago. Costume designer Marilyn Vance-Straker did exhaustive research and then dug up authentic suits from antique clothing stores and created others to match the aesthetic, while Richard Bruno and Henry Stewart were responsible for Robert De Niro's gangster style; Giorgio Armani contributed suits as well.
The Age of Innocence (1993)

Martin Scorsese's 1977 evocation of the late 1940s musical era, New York, New York, was certainly striking, but we give the nod for his most stylish work to his adaptation of Edith Wharton's novel, which brought the high society life of late 19th century New York to vivid, if stultifying life. (We can almost feel our throats constricting from the high collars.) Gabriella Pescucci received the Academy Award for her amazing costumes.
Moulin Rouge! (2001)

Baz Luhrmann's assault on the senses was too frenetic for some critics, but younger audiences lapped it up as a delirious explosion of sight and sound. More than a decade later, it feels a bit too over-pumped -- seriously, Baz, take it easy on the caffeine! -- but the lavish, daring costumes and exquisite art direction, for which the film won well-deserved Academy Awards, remain endlessly fascinating.
Marie Antoinette (2006)

Costume designer Milena Canonero strikes again! Director Sophia Coppola's bold treatment -- the modern pop songs, the insolent attitudes, the riot of colors -- is taken to another level by multiple Academy Award winner Canonero, whose 18th century party dresses and formal gowns have rarely, if ever, been matched for their sheer bravado. You can easily turn the sound off and simply gaze longingly at the costumes to feel like a true peasant.
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