From Hollywood's Golden Age to modern classics, these are the most stylish movies of all time

Fashion is escapism. It tells a story and lets people create characters or evoke fantasies of times and places far-flung. 

The same can be said about the movies. So when you combine the two, how can one possibly resist? 

From moments which defined decades in fashion to the sort of romantic, decadent looks only realised in the make-believe world of Hollywood, these are some of the most stylish movies ever made. 

32 of the most stylish movies of all time

Breakfast at Tiffany's (1961)

In 1961, the effortlessly elegant Audrey Hepburn brought one of Truman Capote's most iconic characters to the silver screen. Giving Holly Golightly - a New York call girl - a sheen of glamour and refinery, Audrey's opening sequence has become the stuff of legend. 

With a trademark Chignon, oversized black sunglasses and a draped, Givenchy black dress, history was made.

Arguably one of the most famous 'Little Black Dresses' ever made, the outfit is accessorised with strings of pearls, opera gloves and, perhaps most important of all, Holly's breakfast as she takes in the windows of Tiffany & Co on Fifth Avenue.

While that's the most famous outfit, the film is packed full of sleek and chic looks evoking 1960s New York. 

Fashion in Film | £13.97 at Amazon

Illustrated with stunning film stills and beautiful sketches, this book by Christopher Laverty celebrates the contributions of fashion designers to cinema over the last century. A great present for anyone interested in fashion and/or cinema. 

View Deal

The Devil Wears Prada (2006)

A best-selling book written by a former Vogue staff member, The Devil Wears Prada became an instant classic when it was released in 2006. 

With Meryl Streep playing an alleged spin on long-time Vogue visionary, Anna Wintour, and Anne Hathaway playing a plucky journalist who gets lured into the world of fashion, the outfits had to deliver - and deliver they did. 

From the Chanel boots which have become meme-worthy to a stunning array of office wear and outerwear inspiration, stylist Patricia Field (who also oversaw the original run of Sex and the City) reportedly spent over $1 million on the film's wardrobe. 

How to Marry a Millionaire (1953)

With Lauren Bacall, Betty Grable and Marilyn Monroe heading the cast, there was no way the wardrobe department could get away with uninspired fashion for the iconic romantic-comedy, How To Marry a Millionaire. 

Following the lives of three friends desperate to bag a man with a bank balance worthy of their tastes, 1950s fashion is on fine display throughout. 

From chic, tailored suits to satin evening gowns, the three leads are never without a stunning outfit - and the film even includes a fashion show sequence! 

The Great Gatsby (2013)

One of the most famous novels ever written - and one which effectively captured the very essence of the fashionable 1920s era - 'Gatsby style' has become a dress code in itself. 

And Baz Luhrmann's adaptation of the classic American novel was a visionary feast, embodying the excess at the heart of the story. 

The glamorous characters, headed by an equally glamorous cast including Leonardo DiCaprio and Carey Mulligan, are decked out in a wardrobe dripping in lace, fringe, pearls and diamonds. 

Funny Face (1957)

Audrey Hepburn is perhaps best remembered for her turn in Breakfast at Tiffany's, with the signature black dress and updo hairstyle forever defining her style. But there's another vehicle for the classic star which any fashion lover should know about. 

Funny Face was Paramount's musical comedy all about fashion. Audrey's character is a bookish thing who gets plucked from obscurity and turned into a high-fashion model, strutting through the streets of Paris with none other than Fred Astaire in tow. Can it get any more romantic - or stylish? 

Replete in bespoke Givenchy designs - with the designer handpicked by Audrey herself - the outfits are ravishing and the Parisian set pieces are equally as escapist. 

Moulin Rouge! (2001)

Moulin Rouge! is the sort of film which was made for the big screen - literally. Not one inch of the screen is wasted in this dazzling epic of love, treachery and Nicole Kidman looking the epitome of glamour. 

From huge elaborate sets - a kitted-out golden elephant is just one example - to satin gowns, burlesque-inspired showgirl outfits and a 2.5 million dollar necklace, it's a feast for the eyes (and Nicole Kidman and Ewan McGregor's surprisingly sweet singing voices are a treat for the ears).

A Single Man (2009)

It was an unexpected move when designer Tom Ford - who has been credited as one of the driving forces behind Gucci's re-emergence in the early 1990s after the brand had lost some of its lustre - turned his impeccable eye to directing feature-length movies as well as crafting haute couture. 

But his first movie, 2009's A Single Man, proved that he was just as meticulous crafting a stylish blockbuster as he was creating a scene on the catwalks. 

The melancholy film - which follows Colin Firth's character grieving the loss of his lover when homosexuality was still taboo - might not be the most uplifting, but the fashion is worth a viewing alone, from sharp, sleek menswear to Julianne Moore's ultra-60s looks.

Funny Girl (1968)

Hello, Gorgeous - Barbra Streisand's iconic first lines in the musical Funny Girl are uttered with the star kitted head to toe in leopard. It sets the tone for what will be a rich, camp and oh-so chic adaptation of the Broadway musical which cemented Streisand's rise to the stratosphere. 

Big hair, big jewels and big song-and-dance numbers are just some of the reasons to watch. Extra style points for Barbra's trademark long nails - never without a sleek manicure. 

The Talented Mr Ripley (1999)

Adapted from Patricia Highsmith's sinister novels, The Talented Mr Ripley may have darkness beneath the surface, but its style is all Riviera chic. 

A young Gwyneth Paltrow, Matt Damon and Jude Law rock an array of linen, colourful suits and glamorous 1950s-era fashion throughout the sun-kissed tale of deception. 

Legendary costume designer Ann Roth is to thank for the inimitable aesthetics of the movie - and her illustrious career continues to flourish, with the star giving 2023's Barbie its technicolour fashion-spectacular. 

Mahogany (1975)

There are famous people and then there are stars. Diana Ross is a star. And the Motown legend - who had already found success in film with her turn portraying Billie Holiday in Lady Sings the Blues - brought her supernova star-power to the silver screen again with Mahogany, a film about an aspiring fashion designer who climbs the ranks but ultimately faces the price of fame and success. 

While the film wasn't considered a success, it's developed a cult following in part thanks to the fashion. 

Fun fact: Diana Ross actually designed a number of the dresses her character wears herself.

Clueless (1995)

Amy Heckerling's Clueless was a modern twist on Jane Austen's Emma - and it has become one of the most beloved and iconic movies which define 90s excess and 90s cool. 

Cher Horowitz - played by Alicia Silverstone - lives the life many could only dream of, complete with a fully-equipped wardrobe boasting Calvin Klein and Alaïa dresses. The most legendary look was her yellow plaid jacket and skirt. 

In total, costume designer Mona May put together a reported 60 looks for the character of Cher.

Nine (2009)

Somehow - almost unbelievably - there was a big-budget musical made that starred (deep breath) Nicole Kidman, Marion Cotillard, Daniel Day-Lewis, Sophia Loren, Penélope Cruz, Judi Dench, Kate Hudson, and Fergie... and, for many, it's been largely forgot. 

Worth a revisit, the film follows a tortured film director, Guido Contini (Day-Lewis) as he looks to right the wrongs in his life, balancing complex relationships with a wife, mistress, muse, agent, and mother.

Costume designer Colleen Atwood - whose previous works include the likes of Chicago and Memoirs of a Geisha - helped capture the look and feel of the film, which is evocative of the high-glamour era of Italy in the late 50s.

Gilda (1946)

Many suggest that Rita Hayworth wasn't just another Old Hollywood bombshell, but *the* Old Hollywood bombshell. And the classic noir, Gilda, should be the only evidence needed to convince people of such claims. 

Draped in a uniform worthy of a classic femme fatale, the starlet slinks her way through endless glamorous outfits in this stylish, dark caper. 

All it took was a simple black dress and the seductive removal of a glove to have the censors (and audiences) sweating when Rita Hayworth's Gilda commanded the stage in a Jean Louis gown for a performance of "Put the Blame on Mame" in the movie.

Marie Antoinette (2006)

A burst of technicolour and a parade of Versailles fashion made Sofia Coppola's Marie Antoinette biopic one for the books (but maybe not the history books, as liberties might have been taken in the name of art).

Leaning into the stereotypes around the last Queen of France, the fashion for the movie is a feast of silks, frills, florals and candy-like colour combinations. 

Let them eat cake - and let them feast on fashion.

Annie Hall (1977)

Diane Keaton has been both a screen and style icon for decades, and her Oscar-winning turn in Annie Hall was one of the lightning rods which sparked it all. 

Annie’s wardrobe - relying heavily on layered menswear, neckties, bowler hats and oversized garments - was not exactly the style expected of Hollywood's leading ladies at the time. 

In her 2011 memoir Then Again, Diane recalled how she dressed herself for the role, taking inspiration from the women of Manhattan. 

"I did what Woody said: I wore what I wanted to wear, or, rather, I stole what I wanted to wear from cool-looking women on the streets of New York... Annie’s khaki pants, vests and tie came from them."

Carol (2015)

Costumer designer Sandy Powell - who has a staggering 15 Academy Award nominations and three wins - transformed the stars of 2015's Carol into perfect examples of rich, elegant, 1950s American glamour. 

Cate Blanchett's Carol - a woman going through a divorce who forges a passionate, secretive lesbian affair - is decked out in the signature style of a bygone era. Fur coats, hats, lapel pins, colourful, fitted suits. 

Coco Before Chanel (2009)

How could any film about Coco Chanel be anything other than stylish?

Telling the story of how Gabrielle 'Coco' Chanel overcame life at an orphanage to conquer the fashion world, Audrey Tatou plays the French designer through a number of chapters of her life.

House of Gucci (2021)

Based on a book of the same name by Sara Gay Forden, House of Gucci chronicles the stranger-than-fiction tale of how the legendary Italian fashion house was formed, lost, and one of the Guccis left murdered by a vengeful ex-wife. 

Naturally, the style on screen is enviable - and excessive. Think more is more - as was the early Gucci style - as Lady Gaga steals the show playing Patrizia Gucci, née Reggiani, the "Black Widow" accused of putting the hit out on her ex-husband, Maurizio Gucci.

Pret-a-Porter (1994)

A film quite literally about fashion had to bring the fashion, and that's what Robert Altman's half-skewering, half-loving satire did in 1994. 

Based on the title given to a collection of clothes (Pret a Porter meaning Ready to Wear, the opposite of the bespoke, one-of-a-kind haute couture) the movie connects a string of separate stories as they all come together for a show at Paris Fashion Week. 

The inimitably glamorous cast includes Sophia Loren, Lauren Bacall, Julia Roberts and Kim Basinger, with cameos from the likes of Jean-Paul Gaultier, Christian LaCroix, Thierry Mugler and supermodel Christy Turlington. 

Mrs Harris Goes to Paris (2022)

The third retelling of the 1958 novel Mrs. 'Arris Goes to Paris by Paul Gallico, 2022's big-screen adaptation starred The Crown's Lesley Manville whose whimsical wish for a custom Dior gown takes her from her life as a cleaner in London to the heart of Paris. 

Working all her life, Mrs Harris finds the joy and escapism in Dior's game-changing 'New Look' designs which defined fashion in the 1950s. 

It's a feel-good film packed full of French fashion and joyful messages. 

Gentlemen Prefer Blondes (1953)

One of the most famous women to have ever lived, a lot of Marilyn Monroe's mystique and legacy are tied up in her position as a style icon and pop culture legend. Case in point: Gentlemen Prefer Blondes.

A musical comedy starring Jane Russell and Marilyn, it includes one of the most memorable (and recreated) moments ever captured - Marilyn's musical number to Diamonds are a Girl's Best Friend. 

The pink satin gown and gloves, the deep red backdrop, the platinum blonde hair - everyone from Madonna to Miss Piggy has been inspired by that moment, and it's only one example of the stylish display on show throughout the movie. 

A Simple Favour (2018)

Gossip Girl alum Blake Lively might best be known for her ultra-feminine red carpet gowns and Rapunzel-worthy blonde locks - including one of the best ever styles from the Emmy red carpet - but her most stylish film appearance to date saw her lean into a menswear-inspired edge. 

Playing the mysterious Emily, Blake commands attention in chic three-piece suits (with detachable dickies), hats and waistcoats with nothing underneath. She even goes full black-tie in a Ralph Lauren tuxedo. 

Phantom Thread (2017)

Visually stunning with darkness beneath the surface, 2017's Phantom Thread is a riveting display of both the beauty and the madness men are capable of. 

The film follows a successful haute couture dressmaker in 1950s London (played by Daniel Day-Lewis) who takes a young waitress as his muse. As such, there are numerous scenes showcasing the craft of couture dressmaking in all its elaborate finery. 

La Dolce Vita (1960)

Legendary filmmaker Federico Fellini's magnus opus, La Dolce Vita, does exactly what is says on the tin - it offers up a slice of the sweet life. Filmed in black-and-white and following the lives of Italy's beautiful and rich, it's a love letter to living a life of glamour, fun and excess. 

It won the Palme d'Or at the 1960 Cannes Film Festival and the Academy Award for Best Costumes.

In one of the film's most memorable scenes (and, indeed, one of cinema's most iconic visuals), Anita Ekberg splashes around Rome's Trevi Fountain in a strapless velvet gown.

Ocean's 8 (2018)

The Ocean's films were already celebrated for their style before the women took control, but with the release of Ocean's 8, the fashion quota skyrocketed. 

By casting the likes of Sandra Bullock, Cate Blanchett, Anne Hathaway and Rihanna in a film centred around the biggest fashion night of the year, the Met Gala, this was always going to be an unmissable movie for fashion lovers.

Cruella (2021)

Celebrated costume designer Jenny Beavan took home the Academy Award for Best Costume Design after overseeing the style revolution of 2021's Cruella. 

Set in swinging London, Emma Stone plays 101 Dalmatians villain Cruella De Vil in the years before she was chasing down puppies to make coats out of. Despite being a prequel, the film doesn't connect much to the classic Disney cartoon and is, instead, a love letter to fashion. 

Emma Stone's Estella/Cruella is a visionary who challenges the more traditional style of Emma Thompson's Baroness von Hellman - a couture designer in London. Under her disguise of Cruella, Estella wages a fashionable war, stealing the spotlight with anarchic fashion looks including a dress made from rubbish bags. 

Emma (2020)

Pastel colours so sweet you'd almost mistake them for icing, square necklines, cap sleeves, and flowing empire waists dominated the costume design for the aesthetically sumptuous Emma in 2020. 

Filmed against gorgeous backdrops of the English countryside or within stately homes, the entire film boasts an escapist style.

Costume designer Alexandra Byrne had previously worked on the likes of The Phantom of the Opera and Finding Neverland.

All About Eve (1950)

The most awarded female in the history of the Academy Awards isn't Meryl Streep, nor is it an actress you may have heard of. It is, in fact, legendary costume designer Edith Head. 

The designer won a record eight Academy Awards for Best Costume Design between 1949 and 1973, and was nominated for a total of 35. If there was a film from the Golden Age of Hollywood requiring a touch of glamour, chances are, Edith Head was involved. 

Take All About Eve. Celebrated for its razor sharp script and glamorous cast (Bette Davis, Marilyn Monroe, Celeste Holm), the film still needs the costumes to give it that sheen. Bette Davis' acerbic actress is always kitted out in furs and elegant looking gowns, while the men look timeless in tailored suits.  

Sunset Boulevard (1950)

Sunset Boulevard is, perhaps, like Hollywood itself - glamorous, larger-than-life, and with a certain darkness hidden beneath the surface. 

The film follows the tale of a penniless writer who, by a strike of fortune (or misfortune), finds himself hiding out at the home of a retired silent movie star. Long forgotten by the industry, but still a diva in her own mind, Gloria Swanson's performance of the deluded Norma Desmond was made even more memorable by her endless parade of fabulous outfits, all designed by Edith Head.

What a Way to Go! (1964)

There's perhaps no greater film to simply stare at rather than focus too much on things as trivial as plot than What a Way to Go!

A screwball comedy from the Golden Age of Hollywood which has slipped under the radar, the film follows a ludicrously wealthy woman (played by Shirley MacLaine, in a role that was meant to be Marilyn Monroe's before her death) who wants to give away her entire fortune. 

She has the bad (?) luck of only attracting men who become wildly successful after she marries them - and it ruins their marriage. From living in a house made entirely of pink (even the swimming pool water is dyed pink) to showcasing a reported $3.5 million worth of jewels throughout, it's a film that any style lover will cherish.

To Catch a Thief (1955)

Alfred Hitchcock's To Catch a Thief is a film that unapologetically worships beauty. 

From the French Riviera setting to Grace Kelly's unrivalled fashion, everything about the movie offers up pure, Hollywood escapism. 

Grace Kelly’s costumes were designed by Edith Head and some of the most memorable looks include a pale blue gown and a pearly-white chiffon dress. These looks helped immortalise Grace Kelly as the classic, icy-blonde beauty. 

Sabrina (1954)

Audrey Hepburn once famously said, "Givenchy's clothes are the only ones I feel myself in."

The Hollywood legend and Hubert de Givenchy himself struck up a close friendship and a working relationship that started with 1954's Sabrina, a romantic drama following a young girl (Hepburn) who must decide between two brothers - one she's loved from afar since a young girl, and another who she gets to know after returning home from an education in Paris. 

From flowing ball gowns to chic tailored trousers, Audrey Hepburn and Givenchy cycle through a litany of luxurious looks in this timeless tale.