9 Women With the Most Influential Style Through the Decades

If your name becomes a signature hairstyle (think Farrah Fawcett hair), it might just be a solid case for style icon status. Or, perhaps singing a song titled “Like a Virgin” while wearing an ironic fashion choice of a white tulle dress and fingerless lace gloves would do the trick (classic Madonna).

From actresses and singers to first ladies and real-life princesses, these are the women whose styles have left a lasting impact on the world.

Josephine Baker

josephine baker, germany 1928, fashion style
Josephine Baker in Germany in 1928.
CREDIT: Rex Shutterstock

In the 1920s Baker was a leading entertainer of the jazz age. Her risqué performance looks were typically topless while a skirt of bananas rested on her hips, making the dancer quite revolutionary in her day. Outside of stage costumes, the St. Louis-born artist maintained a polished yet glam aesthetic, trademarked by accessories (especially ornate hair pieces).


cher, sonny and cher, style, 1970s, stylish iconic women
Cher wears black boots in 1973.
CREDIT: Rex Shutterstock

It’s safe to say that Cher was a risk-taker. Long before it was the norm to bare midriffs and lots of skin at red-carpet events, the singer was making waves with her 1986 Academy Awards look, one of the grandest fashion moments in the show’s 90-year history, which featured a feathered headdress, embellished crop top and black boots. Pioneering crop tops as the norm was just one of the many trends that Cher set, her influence on style peaking in the ’60s and ’70s and lasting well into today.

Diana, Princess of Wales

princess diana, all pink look, british royal tour of australia, 1983
Princess Diana on the British Royal Tour of Australia in 1983.
CREDIT: Rex Shutterstock

Princess Diana’s balloon-sleeved wedding dress is unforgettable. Its 10,000 pearls and 25-foot-long train captured the world’s attention as she was escorted out of her wedding in 1981 by husband Prince Charles, revealing the David and Elizabeth Emanuel design. Her looks only continued to be documented, her royal style showing an affinity for fascinator hats and white heels.

Farrah Fawcett

iconic stylish women, farrah fawcett, nike cortez sneakers, charlies angles
Farrah Fawcett wears Nike Cortez sneakers in the 1970s.
CREDIT: Rex Shutterstock

Few women of the ’70s can deny having coveted Farrah Fawcett’s perfectly teased and tousled hair. The “Charlie’s Angels” front woman was at the epicenter of cool in her heyday, led by her golden locks and girl-next-door glow. Her notorious skateboarding photo from the set of the vintage TV series lives on as an iconic cultural and fashion image. The actress not only made skateboarding look cool and chic, but also touted a pair of classic Nike Cortez sneakers in the process — a look Bella Hadid re-created for the brand as recently as last year.

Audrey Hepburn

stylish iconic women, audrey hepburn, black turtleneck
A film still of Audrey Hepburn.
CREDIT: Rex Shutterstock

There are certain fashion images that are just so classic, they inevitably become emblazoned in history. Since the ’50s, Audrey Hepburn’s all-black ensemble has remained one of the most memorable.

stylish iconic women, audrey hepburn, all black look
Audrey Hepburn in 1956.
CREDIT: Rex Shutterstock

Featuring a simple long-sleeve black shirt, cigarette pants and loafers, the photo shoot portrays the charismatic actress in what is believed to be her most true form. It’s the sheer simplicity yet sophistication of that famous look that has made the actress influential long past her time.

Janet Jackson

janet jackson, style, iconic stylish women
Janet Jackson goes barefoot for a photo in 1993.
CREDIT: Rex Shutterstock

“Ms. Jackson if you’re nasty.” Like Cher, the singer and dancer loved to bare her belly throughout her golden era, mainly the ’90s and ’00s when her style was most prominent. As sister to pop legend Michael Jackson, it’s no wonder that some of her staple wardrobe pieces were borrowed from the boys, especially her knack for pantsuits and oversized blazers. Jackson’s aesthetic is not to be confused as taking a backseat to her brother’s, however.

janet jackson, iconic stylish women
Janet Jackson performs in 1989.
CREDIT: Rex Shutterstock

Without a doubt, she was one of the coolest to ever wear any all-black or all-white look, especially onstage. Giuseppe Zanotti even created custom shoes for the performer’s “Unbreakable” tour in 2015.

Jacqueline Kennedy

Jackie Kennedy Onassis Style
Walking in New York City in September 1968 in Roger Vivier flats.
CREDIT: Shutterstock

Known also as Jackie O.,  the former first lady to John F. Kennedy was elegance personified, whether wearing a suit or an evening gown (paired with evening gloves, of course). Shift dresses and large round sunnies were as much her signature as were the prim skirt suits she donned throughout her tenure as first lady in the ’60s. A pillbox hat and understated pumps were typical finishes for her refined look.

Michelle Obama

michelle obama, style, stylish iconic women
Michelle Obama wears Versace at the White House in 2016.
CREDIT: Rex Shutterstock

Class, grace, poise — these three words can describe former first lady Michelle Obama in both character and style. To have lived in the White House in an age where fashion and politics are more heavily scrutinized and documented than ever, Obama maneuvered the scene like a pro. While she didn’t shy away from popular high-fashion brands, she famously became known for wearing and bringing emerging designers to the forefront as well, including Jason Wu and Tanya Taylor. At a White House roundtable in October 2011, she was quoted as saying, “I try to be thoughtful about spreading the wealth: young designers. Mixing things up is important to me.”

Diana Ross

stylish iconic women, diana ross, berry gordy
Diana Ross, photographed by Berry Gordy in 1975.
CREDIT: Rex Shutterstock

More is more in Diana Ross’ world and that often includes tons of sequins, big hair and an even bigger smile. Ross, who rose to fame in the ’60s as the lead singer for the Supremes, has long had a fabulously vibrant style with an effervescent personality to match. She was spearheading retro white booties long before they made their return in the present day. And monochromatic dressing? She does not miss when it comes to her beloved all-red attire.

diana ross, style, boots, stylish iconic women
Diana Ross in 1980.
CREDIT: Rex Shutterstock

The singer’s fashion imprint is evident in daughter Tracee Ellis Ross, who is becoming an icon all her own. But it’s evident on a global level as well. Just this past fall, she was honored with a Lifetime Achievement Award at the American Music Awards.

Click through the gallery to see more of these stylish iconic women through the years.

Access exclusive content