1. Jean Shrimpton
One of the world’s first supermodels, Shrimpton appeared on the cover of countless magazines, helped to launch the miniskirt, and ushered in a new era of skinny long-legged models. Her fringe and pout are the stuff of legend.
2. Aretha Franklin
The Queen of Soul has won a total of 18 Grammy awards, sold 75 million records worldwide, and was the first female performer inducted into the Rock and Roll Hall of Fame. Aretha stood out among her equally fashionable peers because of the spirit that shone through whatever she wore. The striped dress above could look boring on anyone else, but on Aretha it looks like something amazing is about to happen at any moment.
3. Audrey Hepburn
If you’ve ever thought for a second about how to look beautiful, you’ve probably turned to Audrey Hepburn for inspiration. Although Hepburn’s star first rose in the ’50s, her most iconic role was as Holly Golightly in Breakfast At Tiffany’s in 1961. The little black dress she wears at the beginning of the film defined LBDs forever, and Holly Golightly’s ability to wear high fashion (without it wearing her!) set the bar impossibly high for the rest of time. Hepburn’s style throughout her life could serve as a dictionary definition for grace.
4. Tura Satana
Born Tura Luna Pascual Yamaguchi, her father was Japanese and Filipino, her mother was Cheyenne and Scottish, and Satana was born in Japan. She moved to Los Angeles by the time she was 15, after having been teased mercilessly for her mixed racial heritage and her early adolescent developing figure. She became a very successful exotic dancer and was rumored to have begun a romantic relationship with Elvis Presley after he saw her perform. In 1965, cult film director Russ Meyer cast her in what turned out to be his biggest hit, Faster, Pussycat! Kill! Kill! Satana was personally responsible for crafting much of the look and personality of her character Varla, including her costume, makeup, usage of martial arts, and much of her dialogue. What she created in the process is the most bombastic and influential “bad girls” in cinematic history, a precursor to many of the B-movie stars and Quentin Tarantino’s entire life. In other words, without Tura Santana, there would be a lot less hotness in the world. Lastly, THOSE EYEBROWS.
5. Charlotte Rampling
The English ingenue made her screen debut in 1965 at age 20. She became a star in both English and French cinema after playing Hana Wild in a popular episode of The Avengers, and also became an international style icon due to brazen minidresses and creative pattern situations, as seen above.
6. Connie Chan
Connie Chan was a beloved teen idol of Hong Kong cinema who acted in more than 230 films of a variety of genres. She was so versatile that she sometimes played the male lead, even playing the romantic partner of her fellow teen actress Josephine Siao. Her androgynous acting abilities translated beautifully in her personal style, which was at times boyish and casual, and other times elegant and feminine.
9. Donyale Luna
The first African-American model to appear on the cover of British Vogue. In its April 1, 1966, issue, Time magazine described her as “a new heavenly body who, because of her striking singularity, promises to remain on high for many a season. Donyale Luna, as she calls herself, is unquestionably the hottest model in Europe at the moment. She is only 20, a Negro, hails from Detroit, and is not to be missed if one reads Harper’s Bazaar, Paris Match, Britain’s Queen, the British, French or American editions of Vogue.”
10. Faye Dunaway
First appearing in broadway and then later on stage, Dunaway won a BAFTA and a Golden Globe after her first year in film, and then won the role of the lead in Bonnie and Clyde opposite total dreamboat Warren Beatty (she bear out Cher, Leslie Caron, Jane Fonda, and Natalie Wood). Dunaway is always elegant and yet still totally edgy, the weirdest successful balancing act in style history.
11. Mary Quant
Ms. Quant gets double points because she wasn’t just a style icon — she is also hugely responsible for creating many of the sweetest styles on this list. She pioneered the miniskirt and hot pants, and encouraged women to treat fashion as a fun game and dress to make themselves happy. About the miniskirt (thank you, thank you), she said, “It was the girls on the King’s Road who invented the mini. I was making easy, youthful, simple clothes, in which you could move, in which you could run and jump and we would make them the length the customer wanted. I wore them very short and the customers would say, ‘Shorter, shorter.’”
12. Patti Boyd
Patti Boyd was the first wife of both Eric Clapton and George Harrison, and the inspiration for songs like “Something,” “Layla,” and “Wonderful Tonight.” Her enchanting style, gap tooth, sweet dresses, and flippy hair style all no doubt contributed to her being the ultimate rock ‘n’ roll muse and one of the cutest gals to ever live.
A splashy German model who was sought after in the ’60s, Veruschka was an early adopter of the idea that if you’re important enough, you only need one name (see: Beyoncé, Madonna). When Veruschka was only 5 years old, her father, a member of the German Resistance, was executed for allegedly attempting to assassinate Adolf Hitler. Maybe the experience imbued her with the IDGAF attitude that her pictures project. Today, at age 74, she still sometimes shows up on catwalks, as beautiful as ever and still more concerned with making an impact than she is with making you feel good.
14. María Félix
The most iconic star of Mexican cinema throughout the ’40s to ’60s, María was as refined as ladies can be. Her makeup alone is enough to inspire a million makeovers.
15. Cilla Black
Most famous for the crackling single “Anyone Who Had A Heart,” English singer and actress Cilla Black was a bigger deal in the U.K. than she was in the U.S., but she was a style icon everywhere in the universe. I mean, I can’t even deal with the level of sass perfected in every single one of her looks? Pin-striped girl suit? Check! Kermit the Frog collar that looks more cute than ridic? Check! The cutest stripey shift dress in the world? CHECK!
16. Elizabeth Taylor
You know who she is. I’m just here to look at this headdress.
A Scottish singer and actress most famous for “To Sir With Love” (the song and the film) and being a tiny adorable little firecracker. This dress is a perfect example of the girly, doll-like personal style.
20. Jacqueline Kennedy
The first lady of our hearts managed to maintain her impeccable, influential style throughout her time in the White House and even as she lived through unimaginable tragedy. Her look managed to combine the grace and elegance of classic looks with a charming youthful sensibility that she maintained for her entire life. If only we could all be so perfect.
22. Natalie Wood
GIRL. Wood began acting when she was 4 years old, and when she was 8 she co-starred in Miracle On 34th Street. She received three Academy Award nominations before she was 25 years old, and by the time she appeared in West Side Story in 1961 she was a huge movie star and also the cutest lady ever. I can’t even deal with that cutout beach dress, help.
23. Peggy Moffitt
Popular model Moffitt worked closely with designer Rudi Gernreich, and together they developed a signature new look. The short, strange hairstyles and heavy dark eye makeup gave her a kind of alien look, but she was most famous for modeling the topless “monokini” that Gernreich designed — her husband William Claxton snapped the photo and it appeared in print in Women’s Wear Daily. There’s nothing more important in fashion than confidence and fearlessness, and Moffitt obviously had both in spades.
24. Petula Clark
The English singer, actress, and composer became in international star in the ’60s for her hits like “Downtown” and “Don’t Sleep On The Subway,” as well as her ridiculously adorable big hair and sweet girly style.
25. Nina Simone
Born in Tryon, N.C., in 1933, Nina Simone’s life changed forever when she was denied a scholarship to the prestigious Curtis Institute of Music in Philadelphia, despite years of training as a concert pianist and well-received audition. Simone believed that racism was behind the rejection, and she turned to popular music, playing in small clubs and adding singing to her repertoire. Thank goodness for that. By the ’60s, Simone was already a legend. Throughout it all she maintained a unique and effortless fashion sensibility that also combined elements, including her signature head wraps and unique jewelry.
26. Jane Birkin
Born in England, Birkin auditioned for the French film Slogan in 1968 and won the role despite not being a French speaker. She co-starred with Serge Gainsbourg, and they released “Je t’aime… moi non plus” in 1969, which was subsequently banned on radio stations in Italy, Spain, and the U.K. for its sexual explicitness. I feel sexually explicit just looking at Jane Birkin, so it makes sense.
27. Claudia Cardinale
Born in French Tunisia, this Italian actress didn’t speak a word of the language until she was cast in Italian films. She worked with many of the masters of Italian film — Federico Fellini, Sergio Leone, and Luchino Visconti. She also worked with this striped minidress, or maybe it worked with her. Unclear.
28. Mary Wells
OMFG Mary Wells, you guys. Has anyone ever had better eye makeup? Not to mention her vocals — both sweet and growling — on songs like “My Guy,” “You Beat Me To The Punch,” “Two Lovers,” and “Bye Bye Baby.” She was the Queen of Motown, and I haven’t even mentioned her bangs.
29. Ursula Andress
Swiss-born Ursula Andress was best known for her role as Bond girl Honey Rider in the very first James Bond film, Dr. No, where her white bikini made her a sex symbol and a star. She was quoted as saying, “This bikini made me into a success.” In 1965, she posed for Playboy and when asked why, simply replied “Because I’m beautiful.” True that.
30. Diana Rigg
Best known as Emma Peel on the popular TV series The Avengers, English actress Diana Rigg is an official dame of the British empire, but let’s talk about what she did for leather boots and flippy hair.
31. Marianne Faithfull
The big-eyed folk/pop singer Marianne Faithfull became well known not only for her own hit songs, but also for her five-year love affair with Mick Jagger and her subsequent drug abuse. She inspired many of the Stones’ biggest hits, including “You Can’t Always Get What You Want,” “Wild Horses,” and “I Got the Blues.” It’s easy to see why Jagger boasted about her all the time, just look at those SLEEVES.
33. France Nguyen
Born in France to a French mother and a Vietnamese father, Nguyen was discovered by Life magazine photographer Philippe Halsman and was featured on the cover of the 1958 issue. She became a stage actress that same year, playing Liat in Rogers and Hammerstein’s South Pacific, and the lead role in The World of Suzie Wong opposite William Shatner. She was rumored to have had an affair with a young Marlon Brando, which, if you’ve seen young Marlon Brando, you can appreciate as valid evidence that Nuyen’s game was peak.
34. Grace Slick
Known best as the lead singer of Jefferson Airplane and Jefferson Starship, Slick’s blend of hippie ease and rebellious pre-punk edge was a precursor to the fashions that were to come in the ’70s.
35. Shirley Bassey
Born in Cardiff, Wales, to a Nigerian father and an English mother, Bassey began her career when she was still a teen, recording the scandalous “Burn My Candle” in 1956, when she was 19. In the ’60s, she became best known for recording the theme song to James Bond’s Goldfinger. Her style was girlish and sweet, you can almost see the pink screaming out from the black and white. Unrelatedly, who puts stuffed clowns on their bed?!?!
38. Romy Schneider
An Austrian-born actress who was famous in both Germany and France, Schneider worked with directors such as Otto Preminger and Orson Welles, and had a romance with the heartbreakingly beautiful French actor Alain Delon. Their romance ended in 1963 but they remained friends — and how could you not want to be friends with someone this straightforwardly cool?
39. Dusty Springfield
The most popular female “blue-eyed soul” singers, and one of the greatest voices of all time, Dusty Springfield was born as Mary Isobel Catherine Bernadette O’Brien in London. Her first big hit was “I Only Want to Be with You” in 1963, and she went on to chart countless soulful, emotional pop hits including “I Just Don’t Know What to Do with Myself,” “You Don’t Have to Say You Love Me,” and “Son of a Preacher Man.” Springfield was romantically involved with several different women, including fellow singer Norma Tanega throughout the late ’60s. Although she didn’t exactly “come out” as a lesbian, she did acknowledge her sexuality in interviews, saying to the Evening Standard: “Many other people say I’m bent, and I’ve heard it so many times that I’ve almost learned to accept it … I know I’m perfectly as capable of being swayed by a girl as by a boy. More and more people feel that way and I don’t see why I shouldn’t.” Springfield’s attraction to women and her smoky, sultry voice just bolstered her sensual, soft, feminine image: all big fake eyelashes, silk tops, fitted dresses, and luxe blonde wigs.
40. Mia Farrow
American actress Farrow had a unique look — her cropped hair only bringing more attention to her giant eyes, fine bone structure, and rail-thin frame. She was a model who married Frank Sinatra in 1966, when she was just 21 years old. Farrow rose to fame as an actress, playing naive Allison MacKenzie on the soap opera Peyton Place, and then starred in her first film, Rosemary’s Baby, in 1968. Her performance in the movie was electrifying and terrifying, and further solidified her style as more alien than human, proudly strange and completely fearless.
41. Eartha Kitt
Once described by Orson Welles as “the most exciting woman in the world,” Eartha Kitt was born in South Carolina in 1927 and became a popular singer in the ’40s and ’50s, recording sassy and sexy hits such as “Let’s Do It,” Monotonous,” “Je cherche un homme,” and “Santa Baby.” Kitt spoke four languages and sang in seven (!), earning her near-global fame and adoration. She also acted in a number of Orson Welles films, and then in the ’60s acted in the television series Batman, replacing Julie Newmar to play Catwoman with her own special flair. Kitt always embraced her sexuality without giving up any power, and her style reflects both her purring sex appeal and her liberated attitude.
42. Françoise Hardy
The French singer and actress is perhaps the best known singer of the “ye-ye” pop music movement in France, famous particularly for the hit singles “Tous les garçons et les filles,” “Mon amie la rose,” and “All Over the World” (“Dans le monde entier”). She’s also famous for her girl-next-door-if-next-door-is-a-Paris-café-apartment style, equal parts innocence and mystery. No one has ever looked as good in a leather jacket as she does below, and Mick Jagger once described her as the “ideal woman.” Accurate.
43. Ronnie Bennett (later Ronnie Spector)
The lead singer of The Ronettes, famous for the greatest pop song of all time: “Be My Baby.” Ronnie was born Veronica Yvette Bennett, born to an African-American and Cherokee mother and an Irish father in New York City. She unfortunately ended up marrying her abusive and controlling producer Phil Spector, but while her private life was terrifying, her public persona was flawless, sex-soaked, thick-eyelinered, big-haired perfection.
44. Lena Horne
Born in Brooklyn in 1917, Lena Horne was a Hollywood starlet, singer, actress, and civil rights activist. In the ’50s, she was blacklisted from Hollywood due to her left-leaning political views. But she took it in stride, developing her nightclub singing career and becoming a common sight on evening TV variety programs. She also performed at the legendary March on Washington, and met John F. Kennedy just days before his assassination. In the ’60s, Horne’s style was that of a mature and refined but unfailingly glamorous woman — she wore spectacular gowns and was always impeccably manicured, even while she was making history and never backing down from her beliefs.
45. Julie Driscoll
An English singer and actress, best known in the ’60s for her covers of Bob Dylan’s “This Wheel’s on Fire” and Donovan’s “Season of the Witch,” both as a guest lead singer for the psychedelic band Brian Auger and the Trinity. The former became the theme song to the popular ’90s British sitcom Absolutely Fabulous, which is also a concise way to describe Driscoll’s ’60s style. That hair and those faux bottom lashes!
46. Jacqueline Bisset
An English actress whose big break was 1966’s Cul-de-sac, and later making waves playing opposite Sinatra in The Detective and Steve McQueen in Bullitt. By the early ’70s, Newsweek was declaring that Bisset was “the most beautiful film actress of all time,” and maybe they were right.
47. Dionne Warwick
Her first hit was “Don’t Make Me Over,” allegedly titled after a phrase she herself leveled at Burt Bacharach and Hal David in the production studio. It fits: Warwick remained true to her own saucy, individual style throughout her career as a singer and actress. Her most enduring hit was 1968’s “I Say a Little Prayer,” a booming, joyful tribute to love and life. She embodied that same infectious spirit everywhere she went.
48. Sophia Loren
Italy’s most famous actress of the ’60s or ever, Loren became a movie star and bombshell in the late ’50s and then flipped that success into acclaimed, understated movie roles by the late ’60s. She was the first artist to win an Oscar for a foreign language performance, taking the award for her breathtaking performance as Cesira in Two Women. She was also known for being intelligent and witty, never letting her sexpot persona get in the way of a sharp insight or a funny quip. Her style is equally deep, layering bits of sensuality alongside an uncommon poise and maturity. She was, to many, the most peak picture of what a woman could be.
49. Gina Lollobrigida
Iconic Italian actress and sex symbol and expert at actually pulling off a gigantic hat without it overwhelming her ludicrously beautiful face.
50. Sharmila Tagore
An extremely popular and successful “Bollywood” actress from 1959 and still to this day, Tagore is perhaps best known for 1967’s An Evening In Paris, when she was the first Indian actress to appear on film in a bikini — she also posed in the swimsuit for Filmfare magazine in 1968, shocking Indian audiences. Additionally, as you can clearly see, no one since Tagore in the ’60s has topped her absolutely insanely gorgeous and perfect eye makeup situation.
51. Marsha Hunt
Born in Philadelphia in 1946, Marsha Hunt achieved fame when she played Dionne in the smash musical Hair, a role in which she only had two lines of a dialogue and yet made a huge impact with her presence and that HAIR (which was featured on the cover of the playbill). She had her own band, and in 1969 she met Marc Bolan of T. Rex and the two fell in love at first sight. She also alleges that she inspired the Rolling Stones song “Brown Sugar.” All of this fuss over her makes complete sense if you take a moment to gaze into her eyes in any vintage photograph. Whew, girl.
52. Candice Bergen
The future Ms. Murphy Brown made a splash in her debut, the then-provacative lesbian-themed film The Group. She never backed away from controversy, also participating actively in political activism, once participating in a “Yippie” gag with Abbie Hoffman. She was also way ahead of everyone else re: Leaning In and looking sharp as hell with a powerful and mature professional sense of style that didn’t cater to anyone but her own dang self.
53. Nancy Kwan
One of the first actresses with an Asian background to be accepted and considered a sex symbol in the U.S., Kwan’s first big break was in the film version of the popular show The World of Suzie Wong, which was a major sensation. Although Kwan was born in Hong Kong, she was actually Eurasian and the makeup artists on the film endeavored to make her look ‘more Chinese’ by slanting her eyes and heavily plucking her brows. IRL, Kwan was a revelation: joyful, gorgeous, and buoyantly assembled.
54. Lola Falana
Dancer-singer-actress Lola Falana was a dancer and Broadway star, and later a major star in Italian film despite being born in New Jersey and not knowing a lick of the language until she started acting. She was mentored by Sammy Davis Jr. and matched him in unchartable levels of charisma and charm.
56. Diahann Carroll
Born in the Bronx, Carroll was a successful stage and screen star who played the title role in the 1968 TV series Julia, the groundbreaking series in which she played nurse Julia Baker. Diahann was impeccably perfect and put together at all times, as every cop in the above picture has clearly, uh, noticed.
57. Honor Blackman
Also known as PUSSY GALORE (!) in the Bond film Goldfinger, but looking much more distinguished here IRL. Very Joan Harris.
59. Brigitte Bardot
A world-famous French bombshell and actress who was the subject of a 1959 Simone de Beauvoir essay declaring her a “locomotive of women’s history” and the most liberated woman of post-war France. Bardot’s style was unabashedly sexy, but not because of skimpiness (although that was sometimes the case too) — it was the proto-YOLO confidence that she expressed every time she stepped outside.
Teenage supermodel Lesley Lawson (née Hornby), better known as “Twiggy,” was declared “The Face of ‘66” after agreeing to get her hair cropped short by celebrity hairdresser Leonard. Her signature look was both boyish and whimsically feminine — a stick-thin figure, the haircut, exaggeratedly long fake eyelashes, and adorable boxy short dresses. It’s easy to see what an influence her look has had on fashion ever since, even though Twiggy retired from modeling just a few years into her career, saying, “You can’t be a clothes hanger for your entire life.”
CORRECTION: Ali McGraw won a Golden Globe award for Goodbye, Columbus. A previous version of this story was so distracted by her hair that it misstated the name of the award. (11/30/13)