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14 Classic Icons of Style and Fashion

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14 Classic Icons of Style and Fashion

With trends and influencers gaining and losing popularity quicker than ever, a look back at style icons of decades past reminds us that style is forever. However, the icon gets thrown around far too often. To qualify as one, especially in the now oversaturated realm of fashion, their singular style must evoke images, stories, and other memorable moments we carry throughout our lifetimes.

These sartorial innovators remind us that through style, one can transform fashion from something that you merely put on your body into statement-making moments that speak to who they are and the world they live in. Take, for instance, Katharine Hepburn and Josephine Baker—while one was known for wearing pants and the latter for barely wearing anything, these icons used their style to break free of the conservative norms of their times.

Even our vocabulary has been influenced by these style stars, with Audrey Hepburn and Twiggy becoming synonymous with terms like “the little black dress” and “mod” fashion. No matter what their outfits may conjure up in our minds, the fact remains that there have always been stylish women who have encouraged us with their barrier-breaking sense of style and have pushed both society and the fashion industry forward.

Ahead are the 15 classic style icons that have impacted everything from our sportswear and club clothes to Halloween costumes.

Josephine Baker

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The roaring 20s wouldn’t have been the same without Josephine Baker’s fabulous fashions. Baker’s signature look of cropped hair, fringed flapper gowns and over-the-top headpieces broke free of the stodgy dressings of the past, and the performer’s style became emblematic of the decade’s more liberated spirit. On stage, Baker mesmerized audiences with her showy costumes (who can forget her iconic banana skirt?) and tantalizing moves, but off stage, Baker adopted a gender-bending wardrobe of classic menswear pieces like tailored tuxedos, top hats, and bowties which left society in awe of her thought-provoking style.

Anna May Wong

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Born to humble beginnings in turn-of-the-century Los Angeles, Wong’s career in silent films helped her star rise, and she went on to become Old Hollywood’s most famous Asian American actor. Wong’s successful acting career earned her widespread acclaim, and she became known not just for her film roles but also for her one-of-a-kind beauty and style. Her sleek bob and lacquered lips were emulated by women the world over, while the Asian-inspired costumes she wore on-screen gave a glimpse, albeit through a Hollywood lens, of her beloved culture and heritage.

Katharine Hepburn

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No one broke the style mold quite like the outspoken trailblazer Katharine Hepburn. The lauded actress has won more Academy Awards than any other actor in history, shunned the glitz and glam of Hollywood dressing, and instead adopted a wardrobe of American sportswear staples such as sharp button-down shirts, tailored suit jackets, and perhaps most controversially, pants. We might not think of wearing pants as very forward-thinking, but in the 1930s and ’40s, a woman of her prestige refusing the societal fashion norms of modest “ladylike” dressing seemed simply unfathomable. However, with Hepburn leading the charge, wearing pants eventually became not only widely accepted but an essential wardrobe staple for women all over the world.

Marilyn Monroe

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This starlet proves that diamonds and style are a girl’s best friend. While actress Marilyn Monroe lived a storied life that mirrored the many ups and downs of the characters she played on-screen, one thing that remained a constant was her love for fashion. Monroe unapologetically embraced femininity to the fullest by donning form-fitting hourglass silhouettes, flashy hues, and dangerously plunging necklines—all considered sartorially daring in her heyday. Thanks to costume designer William Travilla, many of Monroe’s film costumes are still instantly recognizable, such as the cotton-candy pink gown with matching gloves she wore in “Gentlemen Prefer Blondes” and the billowy white pleated halter dress from “The Seven Year Itch”.

Grace Kelly

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Another blonde icon who ruled the 1950s was actress Grace Kelly. As a muse of director Alfred Hitchcock, Kelly often portrayed icy perfection on screen with perfectly coifed hair, polished pearls, and a crisp, chic wardrobe. However, once she married Prince Rainer of Monaco, she forever became known to Americans as the style personification of a regal, glamorous, and jet-set lifestyle. Even the accessories she carried in her daily life reached icon status—as seen in the case of the Hermes saddlebag she carried to conceal her pregnancy. The style became known as the “Kelly bag,” and even today, it still commands a long waiting list for those longing to have one of their own.

Audrey Hepburn

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Hepburn was a starlet who was known for many things, from her stellar movie career to her philanthropy, but also her style. With a European sophistication and timeless approach to fashion, Hepburn has become a style icon for the ages. She was able to brilliantly balance the grandeur of evening wear as seen in her famous costumes from “Funny Face” to “Breakfast at Tiffany’s’—which practically helped invent the term “Little Black Dress.” The “LBD” has truly reached the upper echelons of fashion and is considered one of the most essential wardrobe must-haves in existence. However, off-screen Hepburn looked impossibly chic in more casual clothes like turtlenecks, capris, and ballet flats. The balance between refined elegance and effortless chic has made Hepburn’s style eternal and still covetable to this day.

Jacqueline Kennedy Onassis

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Even though Jacqueline Kennedy Onassis wasn’t a performer, she played many roles, such as wife, mother, and a political and societal fixture who championed numerous philanthropic endeavors. However, the former first lady is widely regarded as a bonafide style icon who inspired millions with her impossibly chic wardrobe and elegant demeanor. A fan of pillbox hats, oversized sunglasses (today aptly called “Jackie O” sunglasses), sleeveless shift dresses, silky head scarves, and strands of pearls, Kennedy Onassis’ wardrobe became the epitome of elegance—and for many, the blueprint for their style inspiration.

Twiggy

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This British rose changed the modeling industry when she broke out on the scene during the swinging 1960s. Born Lesley Lawson, the model who earned her “Twiggy” nickname from a hairdresser, became the personification of the overwhelming dominant trend of the time, “Mod” fashion. Characterized by shift dresses, miniskirts, knee-high boots, and bold geometrical patterns on brightly colored clothes, the “Mod” trend was a radical departure from the demure day dresses of the previous decade. Twiggy became what many associate with the trend, and it is still to this day. With her doe-like eyes, innocent allure, and almost otherworldly poise, Twiggy reshaped the expectations of what models could look like and helped push the fashions of her time toward modernity.

Elizabeth Taylor

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If two words sum up Elizabeth Taylor’s decadent style, they would be dresses and diamonds. The legendary actress effortlessly blended in with the trends of the time. From donning circle skirts in the ’50s, Pucci prints during the ’60s and caftans throughout the ’70s, Taylor consistently elevated them to an impossibly glamorous degree. Her secret-style weapon? Diamonds. An impossibly vast array of them. Rarely was she ever seen at an event without a full suite of the finest pieces that one could even imagine. Taylor’s penchant for fine jewelry led her to amass a collection that would be the envy of most museum exhibits and even inspired her perfume, White Diamonds—which has remained an international bestseller since its launch in 1991.

Cher

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Cher has always been a style chameleon. From her bohemian chic and disco-glam diva looks from the 1960s and ’70s to the sheer bodysuits and futuristic fashions of the 1980s and ’90s, Cher tended to flip the script on whatever the trends of the moment were and made them feel uniquely her own. One constant throughout her style career was her longtime collaboration with costume designer Bob Mackie. Together, they conjured up an awe-worthy array of looks that combined brilliant sequins, fabulous feathers, and slinky silhouettes that still permeate the style zeitgeist today as the pinnacle of flashy fashion. Need proof? Look no further than the recent stylings of Kim Kardashian, Miley Cyrus, and Normani, all of whom have embodied the songstresses’s iconic Bob Mackie looks.

Dolly Parton

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While “Coat of Many Colors” is one of Dolly Parton’s greatest hits, her wardrobe of many colors has cemented her place in the style Hall of Fame. Never one to follow fashion trends, Parton has stuck to her signature look— when describing her style, she once said, “There was this one woman (in a Sears catalog), I thought she was beautiful and, you know, she had the peroxide hair, and she had it all piled up on her head and had red fingernails and red lipstick and, you know, wore her powder. And I just thought she was the prettiest thing I’d ever seen.” This playfully bold approach to style, which often went against notions of what was expected of a country singer and a style icon, has helped Parton win the hearts of millions. With the resurgence of Western style and a duet on Beyonce’s Cowboy Carter album, Parton is as relevant as ever, and so is her unforgettable style.

Stevie Nicks

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From singer, songwriter, witchy enchantress, bohemian hippy, and gypsy rocker to the Gold Dust Woman, Stevie Nicks has adopted many monikers, but her signature remains singular. Nicks has been able to cement her style icon status by crafting a carefully curated look that effortlessly combines her fashion and songwriting, making you realize that she is indeed the living embodiment of the free-spirited nature she so often sings about. Her outfits will immediately call to mind flowy chiffon frocks, mainly in the black and white variety, romantic poet-sleeved blouses, 70s high-waisted jeans, and, of course, her go-to accessory: silky fringed shawls.

Grace Jones

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This multi-talented Jamaican model, singer, and actress took the ’70s and ’80s scene by storm with her bold avant-garde style. Jones’ striking style, shaved hair, and androgynous presence made her the muse of the hottest designers of the time, like Azzedine Alaia, Halston, and Yves Saint Laurent. Jones always commanded the room, whether she was dancing the night away at Studio 54 or sashaying down the runway. Often clad in outrageous, skin-baring outfits or demurely draped dresses, Jones’s style is an intriguing balance between familiarity and modernity. Her stylish impact continues to influence and inspire her contemporaries of today, like Lady Gaga, Rihanna, and Solange Knowles, reimagining many of the looks that made Jones a style icon.

Madonna

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No one’s style has morphed over the years quite like Madonna. The queen of reinvention continuously evolves her style to adapt to the times while still being thought-provoking. From her club kid and material girl aesthetic, cone bras (courtesy of Jean Paul Gaultier), sleek minimalism, and zen bohemia, Madonna has always used her style as an extension of her artistry. Her outfits have become just as famous as her chart-topping hits. They are the inspiration for moments that have become iconic in their own right. As the years go on, Madonna proves she’s willing to uphold her icon status through her buzz-worthy fashions.

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