The 40 most stylish women in history

by Katherine West Slevin

Angela Davis—an American political activist, scholar and author—achieved notoriety in the 1960s as a civil rights activist and leader of the Communist Party USA. She quickly became a symbol of the “Black is Beautiful” movement, inspiring generations of African-American women and girls to go natural with her iconic afro and 1960s garb.

It may have taken Princess Diana a while to come into her own in terms of fashion, but it was well worth the wait. Elegant yet approachable, Diana was renowned for her style. Despite her close ties with the fashion world, Diana was best known for her humanitarian and charity work, bringing light to countless issues from HIV/AIDS and leprosy to landmines and homelessness. 

Routinely topping the world’s best-dressed lists, Kate Middleton, Duchess of Cambridge, follows well on the heels of her late mother-in-law, Princess Diana. A philanthropist in her own right (another attribute she shares with Diana), Kate expertly uses the spotlight to illuminate social issues.

Puerto Rican-born Rita Moreno is an accomplished singer, dancer and actress. The first performer, and only Hispanic, to secure the elusive EGOT (an Emmy, a Grammy, an Oscar and a Tony), Moreno is best known for her role as Anita in “West Side Story.” As renowned for her style and beauty as for her principles, Moreno (who in rebellion against stereotypical Latina roles refused to make a movie for seven years after “West Side Story”) remains a fashion icon at the age of 81.

Contemporary Indian and Bollywood actress, Aishwarya Rai Bachchan has gained international recognition for her acting, modeling and humanitarian work. Widely regarded as one of the most beautiful and stylish women in the world, Rai was also appointed the first Goodwill Ambassador of Smile Train, an international charity that provides free cleft lip and palate surgery for children. In addition, she serves as Goodwill Ambassador for UNAIDS and is a UN Microcredit Spokesperson. Rai also supports a number of causes, including animal rights, education for underprivileged girls and efforts to eradicate blindness and polio in India. Now that’s style. 

Twiggy, born Lesley Hornby, is arguably the world’s first supermodel. With her British mod fashion, short locks and striking eyelashes, she epitomized 1960s fashion. After officially retiring from modeling in 1970, Twiggy enjoyed success in acting, singing and activism (most notably in support of breast cancer research and animal welfare). At 63, Twiggy is still inspiring fashion trends with her fashion line and blog. 

Diane von Fürstenberg, a former German princess, is the definition of fashion royalty. A recognized icon of female empowerment, the Belgian-born designer’s inspired jersey wrap dress is flattering, comfortable and became a recognized symbol of the women’s liberation movement. An accomplished philanthropist, von Fürstenberg works through her family foundation, Vital Voices, and the annual DvF Awards to support women’s causes, social entrepreneurship, community building, education, human rights, arts, health and the environment.

Mary Quant was instrumental in shaping British mod culture and fashion during the 1960s. Often credited with inventing hot pants, the miniskirt and colored patterned tights, the London-based fashion designer is an accomplished entrepreneur who skillfully turned a small clothing shop into a multimillion-dollar empire.  

Bronx-born Diahann Carroll is the embodiment of glamour. A Broadway star and Hollywood icon known for always being flawlessly dressed, her lasting legacy will be one of breaking color barriers. Exploding onto the scene in the 1960s, Carroll was the first African-American actress (not depicting a maid) to star in her own television series and the first to win a Tony for best actress.

Swiss actress, plus-size model and fashion designer Stephanie Zwicky challenges the notion that svelte equals beautiful. “A woman’s style has nothing to do with her size or the number on a label. It’s much deeper and more interesting than that,” says Zwicky, who also pens the fashion blog Le Blog de Big Beauty from her home in Paris. Logging nearly a quarter-million readers per month from around the globe, Zwicky has quickly become an inspiration and style icon for women of all sizes.