The 100 Most Stylish Contemporary Characters in Movies, Ranked

MOVIE Challengers (2024)

PORTRAYED BY Zendaya and Josh O’Connor

COSTUME DESIGNER Jonathan Anderson

Inspiring a revival of tennis core, this erotic tryst with costumes designed by now Dior creative director Anderson (at the time at Loewe) let the high-end fashion do the talking for Zendaya’s feisty character, caught in the middle of this aesthetically pleasing love triangle. Sorry, Mike Faist, but Josh had the edge on style here, the way he wore those button-downs and cutoff tees … a prelude to those future collabs with Anderson.

MOVIE Drive (2011)

PORTRAYED BY Ryan Gosling

COSTUME DESIGNER Erin Benach

Driver’s singular look became the focus of this movie, in a modern echo of Brando. Gosling wears a black tee and black jeans under an ivory satin quilted bomber jacket, with a gold scorpion embroidered on the back, custom-made by Richard Lim, a one-off piece — although 27 copies were made for shooting, with action sleeves for motion.

MOVIE The Hunger (1983)

PORTRAYED BY Catherine Deneuve

COSTUME DESIGNER Milena Canonero

Style perhaps won over substance, but the film nonetheless remains a cult creative classic, noted more for its beautiful design and cinematography than for its silly vampire plot. Deneuve in her mostly YSL wardrobe, blending 1980s new wave with a ’40s film noir elegance, was a saving grace and made for the chicest of modern gothic heroines.

MOVIE Reality Bites (1994)

PORTRAYED BY Winona Ryder

COSTUME DESIGNER Eugenie Bafaloukos

With its grunge-inspired aesthetic — floral maxi dress, flannel shirts, boyfriend jeans, tortoiseshell shades, Mary Janes — the seminal Gen X movie was anti-fashion, and so, therefore, fashion. Ryder emerged as a style legend in her own right, wearing vintage to the red carpet, taking her character with her.

MOVIE Girl, Interrupted (1999)

PORTRAYED BY Angelina Jolie

COSTUME DESIGNER Arianne Phillips

By giving the troubled Lisa those self-chopped bangs, vintage pieces and deliberately monochrome choices to drain her of color, Phillips gave Angelina Jolie the extra edge she needed for her Academy Award-winning performance.

MOVIE Clueless (1995)

PORTRAYED BY Alicia Silverstone

COSTUME DESIGNER Mona May

Visit an American Girl shop these days, and you may be pleasantly surprised to see a doll of Cher Horowitz (and Dionne!), yet another affirmation of how indelible these characters and their wardrobes have become. A whopping 59 outfits and the revolving closet may have had something to do with that.

MOVIE 9 to 5 (1980)

PORTRAYED BY Lily Tomlin, Dolly Parton and Jane Fonda

COSTUME DESIGNER Ann Roth

With a dream cast and in the expert hands of Roth, the office comedy is cleverly costumed to illustrate the gender struggles of women in a male-dominated workplace, each character so beautifully fleshed out through their wardrobe choices: Tomlin strong and modern, Fonda still vulnerable after a divorce, and Parton so charmingly Southern.

MOVIE Field of Dreams (1989)

PORTRAYED BY Kevin Costner

COSTUME DESIGNER Linda Bass

That brown leather jacket — OK, perhaps Top Gun helped, but let’s give this one to Costner — became a symbol of the times and is still referenced today. If you wear it, they will come?

MOVIE An American in Paris (1951)

PORTRAYED BY Gene Kelly

COSTUME DESIGNER Orry-Kelly

Gene Kelly, with his athletic yet supple build, is a stylist’s dream. Many a men’s editorial story has paid homage to his panache, and An American in Paris is the archetypal look we’re keenest to replicate, with those ankle crop pants, tight short-sleeve polo tops, white socks and loafers.

MOVIE Casablanca (1942)

PORTRAYED BY Humphrey Bogart

COSTUME DESIGNER Orry-Kelly

Bogart finally broke through with Casablanca, his first romantic lead, spending a good part of the movie smoldering in the iconic trench (apparently made by Burberry, although he wore his own personal Aquascutum trench in the promotional photos) and fedora (by Borsalino, of course), dangling a cigarette and standing around in the plentiful rain even though the movie is set in May and in bone-dry North Africa.

MOVIE Midnight Cowboy (1969)

PORTRAYED BY Dustin Hoffman and Jon Voight

COSTUME DESIGNER Ann Roth

The contrasts (and sexual tensions) between Voight’s flamboyant Texan hustler and Hoffman’s seedy Italian bum — the two-hander’s odd couple — were strikingly expressed in their seemingly incompatible wardrobes without the actors having to say a word. As GQ said, “One man’s heterosexual hero is another man’s gay icon.”

MOVIE The Crying Game (1992)

PORTRAYED BY Jaye Davidson

COSTUME DESIGNER Sandy Powell

Trust three-time Oscar winner Powell to have the sensitivity required to dress one of the most iconic transgender characters memorialized onscreen.

MOVIE Fantastic Mr. Fox (2009)

COSTUME DESIGNER Félicie Haymoz

The meticulously crafted costumes in this stop-motion movie are no less exquisite for being worn by puppet animals. From Mr. Fox’s corduroy suit (which would not look out of place on director Wes Anderson) to Badger’s pinstripe three-piece, no detail was missed, no minute stitch or accessory skipped. Instead they were just made miniature.

MOVIE Fight Club (1999)

PORTRAYED BY Brad Pitt

COSTUME DESIGNER Michael Kaplan

We get it, we’re not supposed to talk about fight club. But can we discuss the fashion for a second? Tyler Durden’s style perfectly embodied a certain turn-of-the-millennium masculine aesthetic. Designed by Kaplan, who also worked on Blade Runner, the look had a nihilistic eccentricity that paired well with the leftovers of the grunge era and thrift-shopping trends of the time.

MOVIE A Hard Day’s Night (1964)

PORTRAYED BY George Harrison, John Lennon, Paul McCartney, Ringo Starr

COSTUME DESIGNER Julie Harris, with Dougie Millings (tailoring)

Whoever had the idea to get the Fab Four on film in a lighthearted caper set against their natural backdrop of screaming fans and pressured managers, in skinny suits and skinny ties … hats off. (The goofier Help!, made a year later, is also worth checking out!)

MOVIE A Clockwork Orange (1971)

PORTRAYED BY Malcolm McDowell

COSTUME DESIGNER Milena Canonero

The eyelashes, the bowler hats, the mime-like white outfits, all blurring class and gender — the style in this subversive Kubrick masterpiece is so assured that it’s hard to believe this was the first film to employ costume designer Canonero, who would go on to be nominated for nine Academy Awards and win four.

MOVIE Funny Face (1957)

PORTRAYED BY Audrey Hepburn

COSTUME DESIGNERS Edith Head and Hubert de Givenchy

When Jo meets Dick Avery (Fred Astaire, whose character was based on photographer Richard Avedon), fashion sparks fly and fashion history is made. With costumes by eight-time Oscar winner Head and de Givenchy, how much better can it get?

MOVIE Belle de Jour (1967)

PORTRAYED BY Catherine Deneuve

COSTUME DESIGNER Yves Saint Laurent

This movie by surrealist master Luis Buñuel marked the beginning of Deneuve’s long partnership with Saint Laurent, who dressed both the character of Séverine and her alter ego Belle de Jour in contrasting palettes and fabrics, the respectable versus the promiscuous.

MOVIE Suspiria (1977)

PORTRAYED BY Jessica Harper

COSTUME DESIGNER Pierangelo Cicoletti

Visually very different from Luca Guadagnino’s 2018 remake, the Dario Argento horror original stands out for its ’70s styles and vivid colors — in both its costumes and its dramatic set direction. A must-watch for fashion-forward cinephiles.

MOVIE Gilda (1946)

PORTRAYED BY Rita Hayworth

COSTUME DESIGNER Jean Louis

The classic femme fatale using all her feminine wiles and her calculated wardrobe choices to seduce and manipulate the male characters, Hayworth’s Gilda is the textbook example of the 1940s bombshell. Having survived the war while the men were away fighting, she comes from a place of power, slightly threatening to members of the patriarchy but at the same time irresistible to them in her sexuality.

MOVIE The Red Shoes (1948)

PORTRAYED BY Moira Shearer

COSTUME DESIGNER Hein Heckroth

A dazzling postwar aesthetic extravaganza with such clever and symbolic use of the titular hue: the red shoes, the red eyeliner, the red lips. The whole vision borders on surrealism, mixing dance and drama against a backdrop of painterly sets and photogenic locations, with impeccable costume design throughout.

MOVIE The Wild One (1953)

PORTRAYED BY Marlon Brando

A prime example of film costume influencing fashion for decades after the character was created, even though apparently Brando just pulled Johnny’s signature pieces from his own closet. The leather jacket, tee, 501 jeans, engineer boots and, of course, the peaked mariner’s cap all went together to form a persona that lives on to this day, forever merging Johnny with Brando himself.

MOVIE Alfie (1966)

PORTRAYED BY Michael Caine

WARDROBE SUPERVISOR Jean Fairlie, with Douglas Hayward (Caine’s suits), Jack Dagemais (Shelley Winters’ wardrobe)

This movie about a well-dressed cad with a bevy of ladies following him around put Caine on the map as the quintessential swinging ’60s Londoner. Alfie seems to have a new outfit for every day of the week, each more sharply tailored the next.

MOVIE Leon: The Professional (1994)

PORTRAYED BY Natalie Portman

COSTUME DESIGNER Magali Guidasci

Guidasci said she started with the boots and worked her way up before a 12-year-old Portman was even cast. She was careful to avoid the Lolita comparisons, as well as sartorial similarities to Jodie Foster in Taxi Driver, another character trapped between childhood and womanhood in a violent world. The result was the unique Mathilda, with her red-knit cap, brunette bob, Army green bomber jacket and sheer determination of spirit.

MOVIE Butterfield 8 (1960)

PORTRAYED BY Elizabeth Taylor

COSTUME DESIGNER Helen Rose

Taylor and Rose are said to have been close friends. The two had worked on the iconic looks for 1958’s Cat on a Hot Tin Roof, and while that film’s feline white slip certainly left a lasting impression, Butterfield 8 adds more luster with coats and cocktail dresses, plus stunning jewelry pieces. (See page 136 for more on Taylor’s Oscar win.)

MOVIE La Piscine (1969)

PORTRAYED BY Romy Schneider and Jane Birkin

COSTUME DESIGNER André Courréges

Truly a movie of the beautiful people (we’re not even including Alain Delon here), with Schneider and Birkin glowing poolside in Technicolor. Whether wrapped in a beach towel, or in a bikini or a one-piece, their natural confidence as women is a wondrous sight.

MOVIE The Harder They Come (1973)

PORTRAYED BY Jimmy Cliff

COSTUME DESIGNER Antoinette Messam

In this low-budget movie that became a reggae cult classic, much of the cast wore their own clothes — Cliff’s wardrobe is said to have been bought at a local Jamaican streetwear store — delighting the fashion world with fake leather jackets, that alligator skin cap and that leopard print shirt.

MOVIE Le Mépris (1963)

PORTRAYED BY Brigitte Bardot

COSTUME DESIGNER Tanine Autré

This is a lesser-known Bardot vehicle — nonetheless notable for its wardrobe and visuals, its stunning Capri backdrop and its dark and challenging storyline, based on Alberto Moravia’s ennui-laden novel. There is not a dress, suit, car or villa that is not utterly desirable.

MOVIE Rebecca (1940)

PORTRAYED BY Joan Fontaine and Laurence Olivier

COSTUME DESIGNER Irene Lentz

As with so many Hitchcock movies, fashion here is a manipulative tool employed to drive the plot forward. This proves especially useful since the title character — the previous Mrs. de Winter — has died, leaving only her wardrobe and her staff to remember her by. Fontaine’s tragic transformation builds off of the masterful costume design, as does Olivier’s intimidation.

MOVIE The Life Aquatic With Steve Zissou (2004)

PORTRAYED BY Bill Murray and Cate Blanchett

COSTUME DESIGNER Milena Canonero

Had they just worn blue overalls, would it have worked? Maybe, but topped with the red-knit Jacques-Yves Cousteau beanies, it became a whole look — a genius touch that communed the whole cast. The addition of Blanchett’s willful, pregnant reporter, dressed in tough Army fatigue-inspired pieces, struck a beautiful balance.

MOVIE The Thomas Crown Affair (1968)

PORTRAYED BY Steve McQueen

COSTUME DESIGNER Theadora Van Runkle

McQueen went from playing Thomas Crown to no-nonsense cop Bullitt in the same year, and the sartorial contrast was a stark one. Crown was an unusual look for McQueen, who generally veered toward the gritty. Here, he was not just costumed but styled to within an inch of his life in exquisite Savile Row three-piece suits with pocket squares, Persol shades, silk neckties and a fob drop pocket watch. Alongside McQueen and Faye Dunaway, the wardrobe was the third star of this movie.

MOVIE Bunny Lake Is Missing (1965)

PORTRAYED BY Carol Lynley

COSTUME DESIGNER Hope Bryce

Lynley somehow manages to look super chic while playing super distressed, as she searches for her missing daughter, the titular Bunny. Whether in a simple trench or a shearling coat and gloves, she shines in this clever and dark thriller.

MOVIE Tár (2022)

PORTRAYED BY Cate Blanchett

COSTUME DESIGNER Bina Daigeler

Tár had to be dressed impeccably in order to live in the most stylish apartment in movies, filmed in a real brutalist Berlin flat whose sophistication and hard edges matched those of the character.

MOVIE Amélie (2001)

PORTRAYED BY Audrey Tautou

COSTUME DESIGNER Madeline Fontaine

Amélie — and Tautou — were both charm personified, and the world fell in love with the French gamine dressed mainly in cherry red and forest green, topped by the Louise Brooks bob. Tautou became a Chanel ambassador and actually went on to play Coco herself in the biopic Coco Before Chanel.

MOVIE Eyes of Laura Mars (1978)

PORTRAYED BY Faye Dunaway

COSTUME DESIGNER Theoni V. Aldredge

Another bottomless source of fashion inspiration, even with its dark John Carpenter script, this is one of the most visual films of the era. Dunaway, as the titular fashion photographer, wore outfits that could hold their own against the coolest designs of the day; the character’s portfolio, meanwhile, was shot by no less an icon than Helmut Newton.

MOVIE Blow Up (1966)

PORTRAYED BY David Hemmings

COSTUME DESIGNER Jocelyn Rickards

Inspired by the real-life fashion photographer and London cad about town, David Bailey, Hemmings’ Thomas is the most casually dressed of all the characters but provides the perfect foil for the fantastically styled cameos from real-life models like Veruschka, Peggy Moffitt and Jane Birkin — all of them as seductive as the Herbie Hancock soundtrack.

MOVIE The Royal Tenenbaums (2001)

PORTRAYED BY Gwyneth Paltrow

COSTUME DESIGNER Karen Patch

Almost every Wes Anderson character could make a case for being included in this list, but there is something about Margot Tenenbaum’s fur coat-wearing, sly cigarette-smoking mix of girlish innocence (the constant barrette) and affected world-weariness that draws on our sympathy and sticks in our memory.

MOVIE Love Story (1970)

PORTRAYED BY Ali MacGraw

COSTUME DESIGNERS Pearl Somner and Alice Manougian Martin

I’m not crying, you’re crying … but not about the fashion. MacGraw, who once worked as assistant to the legendary Vogue editrix Diana Vreeland, added her personal style to the wardrobe here, which became a template for college girls everywhere for years to come.

MOVIE The Witches of Eastwick (1987)

PORTRAYED BY Jack Nicholson, Cher, Susan Sarandon and Michelle Pfeiffer

COSTUME DESIGNER Aggie Guerard Rodgers

Every conversation about this movie inevitably leads to a debate over which witch was the most gorgeous. The answer, of course, is all three (plus a never-more-devilish Nicholson), thanks to the enchanting sartorial touch of Guerard Rodgers, who made brilliant use of designers like Bob Mackie, Cerruti and Azzedine Alaïa.

MOVIE Desperately Seeking Susan (1985)

PORTRAYED BY Madonna

COSTUME DESIGNER Santo Loquasto

Just as Madonna was becoming a household name, she also was becoming a major trendsetter, with her underwear-as-outerwear, statement jewelry, tied hair bands and back-combed-hair signature looks — none of which were received that favorably at the time, but all of which have been revived as cool again more recently by the kids as ’80s fashion once more is revered.

MOVIE Shampoo (1975)

PORTRAYED BY Warren Beatty, Julie Christie, Goldie Hawn

COSTUME DESIGNER Anthea Sylbert

Dressed in an evening shirt and jeans, riding around classic ’70s Los Angeles on his Triumph Daytona and scoring with all the ladies, George (Beatty) seems to have it all, but the calculating mistress (Christie) and the not-so-naive girlfriend (Hawn) make sure he gets his comeuppance in this brilliantly formulated screenplay, co-written by Beatty and Robert Towne.

MOVIE The Man Who Fell to Earth (1976)

PORTRAYED BY David Bowie

COSTUME DESIGNER May Routh

Perfectly cast as the melancholy alien in search of water, Bowie also was role-playing in real life as The Thin White Duke, with his white clothes and shock of orange-dyed hair. The synchronicity worked to perfection in shaping the style of Nicolas Roeg’s weird and wonderful movie.

MOVIE Coffy (1973)

PORTRAYED BY Pam Grier

COSTUME DESIGNER Sandra Stewart

“The baddest one-chick hit squad that ever hit town,” as the tagline went. … The stunning Grier was never sexier or hipper than here, costumed in low-waist jeans, knotted shirts and dresses cut to make grown men blush. The one-two punch of Coffy and Foxy Brown, released shortly after, solidified her status as a genre-defining blaxploitation star.

MOVIE Darling (1965)

PORTRAYED BY Julie Christie

COSTUME DESIGNER Julie Harris

This cynical satire of swinging ’60s London follows Christie as a bored model with lofty ambitions and a gorgeous wardrobe. She moves up the social ladder, eventually marrying an Italian prince, only to be abandoned — but still looks stunning in her Roman palazzo.

MOVIE Three Days of the Condor (1975)

PORTRAYED BY Robert Redford

COSTUME DESIGNER Joseph Aulisi

Aulisi nails it again. This is Redford at his natural best, in a black peacoat or tweed jacket over double denim, slightly intimidating in his handsomeness but at the same time the everyman in aviator readers and shades, rushing around New York and Washington, D.C., with Faye Dunaway in tow. The epitome of ’70s flair, he could do no wrong on the style front.

MOVIE Shaft (1971)

PORTRAYED BY Richard Roundtree

COSTUME DESIGNER Joseph Aulisi

A triumph of designer Aulisi, who apprenticed under two-time Academy Award-winning costumer Ann Roth, Shaft long has inspired couturiers and stylists alike with his cool. Rediscovered over and over, Roundtree still looks suave as hell in leathers and roll necks.

MOVIE Rear Window (1954)

PORTRAYED BY Grace Kelly

COSTUME DESIGNER Edith Head

The queen of the ice blondes, Kelly reached heights of fashion on film with Rear Window, To Catch a Thief and High Society before she retired to the life of a royal. Well after Kelly ceased being available to him as an actress and muse, Hitchcock seemed continually to echo Lisa Fremont’s inspirational costume moments.

MOVIE La Dolce Vita (1960)

PORTRAYED BY Marcello Mastroianni and Anita Ekberg

COSTUME DESIGNER Piero Gherardi

The sweet life, indeed. Peak Italian style with soaking-wet Ekberg and Mastroianni frolicking in the Trevi Fountain, he in the classic black suit and tie of the ’60s and she in a strapless dress purportedly inspired by John Singer Sargent’s 1884 portrait of Madame X. Che bella …

MOVIE Bullitt (1968)

PORTRAYED BY Steve McQueen and Jacqueline Bissett

COSTUME DESIGNER Theadora Van Runkle

The simplest of uniforms once again is made cool by the era and wearer. McQueen’s Det. Lt. Bullitt exudes hard-boiled chic with his brown tweed jacket or raincoat, black pants and black roll neck. Gun holster as accessory. He even pulls off paisley pajamas. The man could do no wrong. Especially not with Bissett on the back of his Triumph, made all the more feminine with her hair bows and scarves.

MOVIE Kaleidoscope (1966)

PORTRAYED BY Warren Beatty and Susannah York

COSTUME DESIGNERS Dorothy Edwards, John Hilling, Marion Foale and Sally Tuffin (York); Anthony Sinclair (Beatty)

This is the platonic ideal of 1960s fashion: Beatty in tuxedos and a red sports car and York as his raspy-voiced sidekick in various feather-trimmed gowns, always running to escape the villains against an excellent London backdrop. The dazzlingly colorful caper features multiple outfit changes and a notable cameo from Clive Revill as McGinnis’ tweed-clad detective father.

MOVIE Pulp Fiction (1994)

PORTRAYED BY Uma Thurman

COSTUME DESIGNER Betsy Heimann

Mia Wallace is a movie-poster designer’s godsend: Thurman in a slick black wig, black low-cut tee, pedal pushers and stilettos. With a cigarette burning, red nails and lips, she was the archetypal ’90s gal not to be messed with and melted hearts around the globe, even as she gets a giant hypodermic needle plunged into hers.

MOVIE Klute (1971)

PORTRAYED BY Jane Fonda

COSTUME DESIGNER Ann Roth

Fonda dyed and cut her hair into a shag and went bra-less to break free from the traditional male gaze to which so many of her 1960s movies had been geared. With this radical fashion statement, she shifted to the looser and more feminist era of the 1970s, keeping the character’s style long after filming ended.

MOVIE Rebel Without a Cause (1955)

PORTRAYED BY James Dean

COSTUME DESIGNER Moss Mabry

As with Monroe’s white dress or Marlon Brando’s leather jacket (see No. 72), Dean’s image will forever be associated with his red windbreaker, white tee and classic blue Lee jeans. The color red was chosen explicitly by director Nicholas Ray and Mabry to evoke blood, rebellion and stylistic daring.

MOVIE The Seven Year Itch (1955)

PORTRAYED BY Marilyn Monroe

COSTUME DESIGNER William Travilla

It’s possibly the most recognized movie image of the 20th century: Marilyn leaning over the grate with the air from the subway blowing up the pleats of her white halter dress, a moment that upstaged other equally splendid looks in this film. Travilla designed the Grecian-style dress, and it has been emulated numerous times — but never equaled.

MOVIE What a Way to Go! (1964)

PORTRAYED BY Shirley MacLaine

COSTUME DESIGNER Edith Head

Not Head’s most famous movie, but perhaps it should be? She designed a veritable shopping list of stunning gowns, with a wig dyed to match each one — and to match each different husband, too, including Paul Newman, Robert Mitchum and Gene Kelly. Plus a cool $3.5 million in Harry Winston jewels! Well worth a gander.

MOVIE Paris, Texas (1984)

PORTRAYED BY Nastassja Kinski

COSTUME DESIGNER Birgitta Bjerke

It’s impossible to forget the image of Kinski with the overly blond bob, the fuchsia mohair dress and those pillow lips glossed up to match. The mix of innocence and seduction strikes such a contrast with the dry desert in which Wim Wenders places her.

MOVIE Reservoir Dogs (1992)

PORTRAYED BY Michael Madsen

COSTUME DESIGNER Betsy Heimann

Was there ever a cooler cat than Madsen himself, not to mention when he played Mr. Blonde, the quiet but ruthless killer in a simple black suit, white shirt, skinny black tie, suspenders and shades? Hearkening to Philip Marlowe himself, it became a ubiquitous uniform of the new noir.

MOVIE Basic Instinct (1992)

PORTRAYED BY Sharon Stone

COSTUME DESIGNER Ellen Mirojnick

The elevated costume design by Mirojnick in this film helped to make this a timeless classic. Early ’90s minimalism will never date, and Stone’s Tramell will forever seduce her audience in that short white dress — and little else.

MOVIE Stray Dog (1949)

PORTRAYED BY Toshiro Mifune

COSTUME DESIGNER Muraki Yoshiro

Akira Kurosawa made nothing but stylish movies, and Detective Murakami, his clean white suit as exacting as his police work, was a standout example of the cinematic chic that set the tone on all the legendary director’s sets.

MOVIE The Philadelphia Story (1940)

PORTRAYED BY Katharine Hepburn

COSTUME DESIGNER Adrian Adolph Greenberg

Hepburn led an early charge for female empowerment in this movie. Even while playing the spoiled heiress, Lord was calling the shots in pantsuits — or “slacks,” as she preferred to call them — and wide-shouldered gowns, while the men in her life had no choice but to fall at her feet.

MOVIE The Big Lebowski (1998)

PORTRAYED BY Jeff Bridges

COSTUME DESIGNER Mary Zophres

Bridges’ slovenly slacker is perhaps not the first image that comes to mind when you hear the words “fashion icon,” but ever since The Dude shuffled onto the big screen in his bathrobe and jelly sandals, or his Pendleton cardigan and pajama pants, a new kind of anti-icon had arrived.

MOVIE 9½ Weeks (1986)

PORTRAYED BY Kim Basinger and Mickey Rourke

COSTUME DESIGNER Bobbie Read

In one of the sexiest movies to come out of the ’80s, Pygmalion-esque John uses fashion to transform Elizabeth into his ideal woman, dressing her in designers such as Azzedine Alaïa, while his own closet is lined with Armani suits. Rourke and Basinger are here at their supremely stylish peaks.

MOVIE When Harry Met Sally … (1989)

PORTRAYED BY Meg Ryan

COSTUME DESIGNER Gloria Gresham

A cult rom-com cannot help but produce cult fashion looks. Ryan’s Sally is the ultimate preppy college girl who grows up to be a feminist journalist, with classic taffeta party frocks, Katharine Hepburn-type pantsuits, white socks and loafers, curly locks and scrunchies. If the menswear-inspired getups ring a bell, it’s no accident: Costume designer Gresham had formerly assisted Annie Hall designer Ruth Morley.

MOVIE Scarface (1983)

PORTRAYED BY Michelle Pfeiffer

COSTUME DESIGNER Patricia Norris

In her breakthrough role, Pfeiffer as Hancock portrayed the ultimate gangster’s moll, mostly in Halston-inspired plunge-neck evening dresses or sharp-cut skirt suits — and of course the hatchet-like blond bob with a slash of a red lip. A minimalist’s dream.

MOVIE Roman Holiday (1953)

PORTRAYED BY Gregory Peck and Audrey Hepburn

COSTUME DESIGNER Edith Head

The most impeccable movie, actress, actor, casting, location, wardrobe … this movie is perhaps faultless on the style front, having been made in 1953, when elegance really was at an all-time high. Who wouldn’t long to dress like either one of these characters, which earned Ms. Head one of her 35 (!) Oscar nominations?

MOVIE Saturday Night Fever (1977)

PORTRAYED BY John Travolta

COSTUME DESIGNER Patrizia von Brandenstein

Close your eyes, and what do you see when you picture Saturday Night Fever? The white suit, the black shirt. The pose. That’s how fashion makes an impact. John Travolta’s moves didn’t hurt.

MOVIE Rosemary’s Baby (1968)

PORTRAYED BY Mia Farrow

COSTUME DESIGNER Anthea Sylbert

The doe-eyed innocent is dressed in cute and playful pieces to emphasize her naivete in Roman Polanski’s dark and disturbing masterpiece. Rosemary caps off her transformation (and her look) by chopping her bob into the sweet pixie cut that became the signature look of the time, pronouncing: “It’s Vidal Sassoon. It’s very in.”

MOVIE American Gigolo (1980)

PORTRAYED BY Richard Gere

COSTUME DESIGNER Giorgio Armani

This raunchy movie almost instantly turned Armani, who dressed Gere in his inimitable unstructured style, from a fashion darling into a household name. The Paul Schrader-directed film was decently reviewed, but it’s mainly the wardrobe we remember.

MOVIE Do the Right Thing

PORTRAYED BY Bill Nunn and Spike Lee

COSTUME DESIGNER Ruth E. Carter

Costumed by the legendary Carter, who worked closely with director Spike Lee, these wildly vibrant looks reveal a fine attention to the details of inner-city Brooklyn life, down to the Air Jordans. Iconic.

MOVIE Dr. No (1961)

PORTRAYED BY Sean Connery

COSTUME DESIGNER Tessa Prendergast, with tailoring by Anthony Sinclair and shirtmaker Turnbull & Asser

Bond is among the few characters to merit multiple showings on any cinematic best dressed list. But no manifestation of 007 can beat Connery’s, specifically in his first appearance as the superspy. Dr. No is supremely and beautifully styled and established the Bond look moving forward; refined, tailored, elegant and embodying the phrase “dressed to kill.”

MOVIE North by Northwest (1959)

PORTRAYED BY Eva Marie Saint and Cary Grant

COSTUME DESIGNER Harry Kress

Grant is the ultimate best-dressed man in Hollywood history, with his Savile Row tailored suits here and in most of his movies. But Saint should not go unmentioned, in the chicest of match sets and dresses (apparently bought on a shopping spree with Hitchcock himself) as Eve and Roger both run from the bad guys in the most elegant era of fashion.

MOVIE Mahogany (1975)

PORTRAYED BY Diana Ross

COSTUME DESIGNER Diana Ross (yes, really)

A showcase of ’70s couture, worn and costume designed by Diana Ross, as her character goes from fashion student to model to designer. The clothes play the most glamorous supporting role in this classic.

MOVIE Annie Hall (1977)

PORTRAYED BY Diane Keaton

COSTUME DESIGNER Ruth Morley

Stylistically speaking, it seems as if Annie Hall really was Diane Keaton, and vice versa. Ruth Morley was the costume designer on this film, and Ralph Lauren’s pieces were used, but Keaton’s influence is everywhere and obvious, and we have her to thank for a menswear-influenced style that really has become known as “Annie Hall.”

MOVIE The Long Goodbye (1973)

PORTRAYED BY Elliott Gould

COSTUME DESIGNER Kent James (men’s) and Marjorie Wahl (women’s)

Of all the different iterations of Marlowe, Gould’s louche interpretation hits the coolest note. In the slim, mismatched navy jacket and pants, white shirt and loosened skinny crimson tie, he just can’t be beat. And his tower apartment shouldn’t go without a mention as the coolest onscreen abode in L.A.

MOVIE Breakfast at Tiffany’s (1961)

PORTRAYED BY Audrey Hepburn

COSTUME DESIGNERS Edith Head and Hubert de Givenchy

No style list would be complete without Holly Golightly, Hepburn’s vulnerable portrayal of the call girl with the chicest wardrobe ever. Each outfit is singular, with no relation to the last, but somehow all are unforgettable.

MOVIE Subway (1985)

PORTRAYED BY Christophe Lambert, Isabelle Adjani

COSTUME DESIGNER Martine Rapin

If you’re a fashion lover and haven’t seen Subway, Luc Besson’s second feature film, you’re missing out on a wellspring of outré 1980s inspiration. Adjani stuns as the Chanel-clad rich girl, punked up with a coiffed mohican (see previous page), matched with the seemingly homeless Lambert, bleached blond and effortlessly chill in his raincoat, living the life in the stations of the Parisian underground.

1. Mrs. Robinson

MOVIE The Graduate (1967)

PORTRAYED BY Anne Bancroft

COSTUME DESIGNER Patricia Zipprodt

It’s hard to comprehend just how provocative it was to portray Mrs. Robinson at that time in cinema, but Anne Bancroft, in her leopard-print dresses and underwear, crafted an iconic character by exuding beauty and bitterness in equal measure.

This story appeared in the March 11 issue of The Hollywood Reporter magazine. Click here to subscribe.