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A Style-Lover’s Guide To The Most Influential Fashion Icons Of All Time

Though style is always evolving and consistently breaking new barriers, there are so many influential fashion icons who are trailblazers in every sense of the word. The world has been blessed with models, actors, performers and designers who created what we would consider “classic” styles today, along with bold looks most of us could only dream of one day emulating. The fashion legends of decades past are the reason we have so many incredible styles from which to choose—and  have influenced nearly every fashion trend to appear from our favorite designers and brands.

From Marilyn Monroe and her iconic white halter dress (You know the one!) to Princess Diana’s relatable, casual style—no matter the fact that she was actual, legitimate royalty—and Naomi Campbell’s influence as a world-famous supermodel in the ’80s and ’90s, there are so many figures who have shaped how we see fashion today. Of course, the evolution of style is ever-changing and adapting to our current world, but we’d be nowhere without the influential fashion icons who have led the way with their legendary ensembles and fearless attitudes. If there’s a trend you absolutely love, odds are, it was inspired by a fashionista from history.

Because it’s always a good idea to know where we’ve been before we can keep moving forward, you’ll find a list of some of the most influential fashion icons of all time below—and the reasons why they’re legendary. Although they might not have realized it at the time, each of these style symbols has had a major impact on the fashion industry and how we view style as a whole. Constantly pushing barriers and using fashion as a form of liberation, the icons below are worth remembering—and celebrating.


Marilyn Monroe

STYLECASTER | Influential Fashion Icons

AP Photo/Matty Zimmerman.

Marilyn Monroe—also known as Norma Jean Mortenson—was, perhaps, the most well-known actress and singer of the 1950s. Of course, her influence wasn’t just limited to her performance abilities, but also her fashion. Her most iconic look, without a doubt, is the white halter dress she wore for the film The Seven Year Itch, which has become the go-to ensemble for anyone replicating Monroe’s style.



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Globe Photos/MediaPunch /IPX.

Cher has had a major style evolution that began in the 1970s—mainly due to the fact she had a close relationship with costume designer Bob Mackie. She not only wore unique, jaw-dropping (and even somewhat unconventional) looks on stage, but also on red carpets as well.


Naomi Campbell

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AP Photo/Remy de la Mauviniere.

Naomi Campbell became one of the most sought-after models in the ’80s and ’90s after being discovered at the age of 15. (!) She’s walked countless runways, and one of the first women to be officially deemed a “supermodel” by the fashion industry. She became a trailblazer in the industry, and even served as the first Black woman to be featured on the cover of several magazines—including French Vogue.


Cindy Crawford

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AP Photo/Andrew Medichini.

Along with Naomi Campbell, we have Cindy Crawford. Arguably one of the most famous supermodels of all time, Crawford gained her success on the runways in the ’80s and ’90s. During this time, too, the model became an influential fashion icon when off-duty. Her red Versace dress worn to the Oscars in 1991 became a must-have look throughout the world.


Diana Ross

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AP Photo/Carlos Rene Perez.

With confidence for days and a willingness to unapologetically stand out with her fashion choices, Diana Ross become one of the most influential fashion icons of all time. She could go from classic gowns to funky on-trend looks in the drop of a hat—and look absolutely incredible in them all.



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Sipa via AP Images.

Anyone alive—and interested in fashion—in the 1960s was no-doubt influenced by Twiggy (also known as Dame Lesley Dawson). She was a British cultural icon and one of the most well-known models of the era—especially due to her thin frame, big eyes, long eyelashes and short hair. The model had a kind of androgynous look that was new and exciting, and the entire world loved it.


Audrey Hepburn

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AP Photo/Giuseppe Messina.

Then, of course, there’s Audrey Hepburn. There’s no denying that Hepburn has had an insurmountable level of influence in fashion. Her sophisticated gowns, classic pearl necklaces and long gloves have become staples in so many designers’ collections through the years—not to mention Halloween costumes.



STYLECASTER | Influential Fashion Icons

Ross Marino Archive/MediaPunch/IPX.

We can’t talk about influential fashion icons and not talk about the one, the only Prince. The singer was known for his incredibly bold (and fun!) on-stage fashion choices, and he consistently pushed gender norms throughout the ’80s—and, quite frankly, all the way until his death in 2016. A true legend, you could always expect something eclectic and exciting from Prince.


Jackie O

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PA Wire.

Jackie Kennedy is most well-known for her stint as First Lady of the United States, but she was also a writer, photographer and socialite before that. While she was in the White House, though, Jackie O became a fashion icon—thanks, in part, to her signature style (big sunglasses, anyone?). The pink Chanel suit and matching pillbox hat worn by Jackie Kennedy when President John F. Kennedy was assassinated is perhaps her most famous look.


Princess Diana

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AP Photo.

Princess Diana wore plenty of gorgeous pieces in the 1980s, but her casual style is what made her so influential—and, honestly, likable. She was often seen wearing what we’d consider athleisure today, along with other cute styles that made her feel relatable. Though she was royalty, Princess Diana stayed down-to-earth with her style, making her one of fashion’s most-loved influences.


Josephine Baker

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AP Photo.

Along with being a famous entertainer in France, French Resistance agent and civil rights activist (!), Josephine Baker was also an undeniable style icon. She was the first Black woman to star in a major motion film in 1927 and such a trailblazer during the Jazz Age. Her iconic costume consisted of a skirt made of faux bananas and a beaded necklace—which became a symbol of the era.


Coco Chanel

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Sipa via AP Images.

Coco Chanel (pictured left) has become synonymous with fashion. And not only fashion in general, but high fashion. She founded Chanel after World War I, moving away from the classic corset ensembles and into more fun, casual and sportier looks. This was a huge shift in what it meant to look “feminine,” and paved the way for thousands of designers to come.


David Bowie

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Werner Baum/picture-alliance/dpa/AP Images.

A rock god who defied gendered fashion norms was—of course!!—David Bowie. While the singer had several different styles during his active years, one of the most famous was his Ziggy Stardust persona. With wild jumpsuits and colorful on-stage outfits, bright hair and a lightning bolt on his face, it’s hard to deny the impact Bowie had on the ’70s and ’80s fashion scene.


Grace Kelly

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AP Photo.

One of the most well-known actresses of the 1950s, Grace Kelly was an influential fashion icon in more ways than one. She practically defined what most of us now consider “classic” styles—and is especially known for her gorgeous wedding dress worn when she married Prince Rainer III in 1956, becoming the Princess of Monaco.

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