Beauties who changed the meaning of pretty

Known for her fierce independence and quick wit, Katharine Hepburn adopted many stereotypically masculine traits: She played sports every morning and rejected glamorous gowns for comfortable pantsuits. Slender and flat-chested, the actress paved the way for women who didn't feel compelled to conform to traditional standards of femininity.

Jane Birkin is often mistaken for being French because she sang a 1968 hit song with her then-lover Serge Gainsbourg. In actuality, she was born and raised in England and came into full flower in the swinging London of the 1960s. If stereotypes were true, then her Britishness might account for her imperfect teeth. But stereotypes are easy labels, and Birkin’s beauty was complicated—and enhanced—by her gap-tooth smile.

Marilyn Monroe and Sophia Loren had nothing on Claudia Cardinale, the Tunisian-Italian actress who broke the mold for curvy women. She is best known for her roles in classic Italian films such as Federico Fellini's 8 ½ (1963) and Sergio Leone’s Once Upon a Time in the West (1968). Her form was so quintessentially feminine that Bob Dylan used a photograph of her on the original album cover of Blonde on Blonde (1963)—he later had to remove it because he hadn’t received her OK.

With starring roles in films by legendary directors such as Woody Allen, Robert Altman and Stanley Kubrick, Shelley Duvall was one of the most sought-after actresses in the 1970s. With her prominent eyes and beanpole figure, Duvall was certainly not conventionally beautiful, but her quirky look and expressive features were mesmerizing.

Arguably one of the best things to come out of the 1980s was the Brooke Shields eyebrow. Her ungroomed arches, which had a youthful, relaxed quality to them, inspired a generation of women to stop over-plucking and start embracing the natural look.

Despite her luminous skin and long limbs, Alek Wek's path to becoming MTV's Model of the Year in 1997 was not an easy one. Born in 1977, Wek escaped to Britain from the civil war in Sudan in 1991 and was discovered by a scout in London in 1995. Since then, the shorn beauty has walked the runway for top designers and appeared in countless ads. In 1997, she was the first African model to appear on the cover of ELLE magazine.

After the impossibly thin supermodels of the 1990s, Lopez's shapely figure—and standout backside—was a refreshing return to normalcy for the average women. The star made it clear that a woman needn't be a size 0 to be desirable.

Diane Von Furstenberg first rose to prominence when she married a German prince in the 1960s (they divorced in '72), but she didn’t become an It girl until she designed the wrap dresses that would make her into a fashion tycoon. Learning early in life that while physical beauty has its advantages, it's what a woman does with her life that ultimately defines her, Von Furstenberg has only become more confident with age.

Not since Grace Jones has there been an androgynous beauty like Kristina Salinovic, whose chiseled cheekbones and angular features complement her deep blue eyes and full lips. Born in Croatia in 1991, Salinovic has appeared on the cover of Italian Vogue and has walked the runway for Jean Paul Gaultier, Lanvin and others. The rising star of the modeling world is setting the tone for a trend towards gender ambiguity.