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Home > Celeb > The Biggest Fashion Icons of All Time, Ranked
Celeb Celebrity Lifestyle

The Biggest Fashion Icons of All Time, Ranked

Maurice Shirley
Published September 4, 2025

If fashion is power, these legends are its rulers. Across decades, they’ve set trends, broken boundaries, and created cultural moments that still ripple through runways and wardrobes today. But here’s the twist: we’ve ranked them! In this definitive list, silver-screen goddesses don’t always come out on top, and daring red-carpet icons rise higher than names once thought untouchable. This list will surprise you, challenge your favorites, and maybe even spark outrage. So, who really deserves the crown?

50. Sarah Jessica Parker

Woman on the red carpet in bright red velvet trousers and a gold bra top with a cropped, jewel-embellished matador-style jacket. Close-up shows her curly blonde hair and vibrant red lip.
Image via ryanhaar on Pinterest

We begin our countdown with Sarah Jessica Parker, who convinced us that a freelance columnist could fund a closet of Manolos and still afford brunch in Manhattan. Sex and the City wasn’t TV—it was a four-season fashion week.

The tutu-and-tank-top opening sequence is still one of television’s most famous outfits. It’s proof that sometimes $5 worth of tulle can make you just as iconic as couture.

“I like my money right where I can see it—hanging in my closet,” Parker believed. She showed us financial planning can indeed come in strappy sandals.

49. Ralph Lauren

Man walking confidently in a distressed leather jacket layered over a black-and-white buffalo plaid shirt and dark jeans, on a wooden floor runway. Close-up shows his silver hair and relaxed smile.
Image via @ComplexStyle on X

Ralph Lauren began with neckties in 1967 and ended up dressing presidents, Olympians, and suburban dads at backyard barbecues. Few designers have made aspirational style this simultaneously chic and mass-market.

His Polo logo became shorthand for “I play tennis… or at least own the outfit.” When Team USA walked into the 2012 Olympics in their blazers, it was peak fashion diplomacy.

“I don’t design clothes, I design dreams,” Lauren once said. He reminds us that sometimes the American Dream comes embroidered on a polo shirt in four different pastel shades.

48. Zendaya

Woman in a one-shoulder iridescent blue and green gown adorned with sculptural florals and dramatic makeup, posing on a flower-lined carpet. Close-up shows her intense eyeshadow, netted fascinator, and floral choker.
Image via @Zendaya_Updated on X

Zendaya doesn’t just attend red carpets—she directs them. With stylist Law Roach, she’s appeared as Joan of Arc in full chainmail, a Disney princess in glass slippers, and somehow, always the moment.

Her 2015 Oscars look with dreadlocks sparked one of Hollywood’s most unnecessary controversies. But Zendaya responded with grace, reminding critics that hairstyles aren’t costumes. She won the night, the argument, and the internet.

“Fashion is a great way to express yourself,” Zendaya explained. She’s the living proof that Gen Z doesn’t dress for approval—they dress for headlines, hashtags, and maybe a viral TikTok edit.

47. Azzedine Alaïa

Black and white photos showing a man with curly hair standing beside a model in a backless mini dress and also seated at a workshop table smiling. Close-up captures his youthful expression and creative energy.
Image via fontdolores and britishvogue on Pinterest

Azzedine Alaïa was the rare designer who didn’t bother with fashion week calendars. He showed collections when he felt like it, and somehow, everyone waited because perfection takes its sweet time.

Nicknamed the “King of Cling,” his sculptural dresses turned supermodels into goddesses. Naomi Campbell adored him so much she basically called him “Papa Alaïa.” Even Grace Jones wore his pieces like armor.

Clueless immortalized him when Cher shrieked, “It’s an Alaïa!” at gunpoint. He proves that if your designs are good enough, Hollywood will write them into the script.

46. Dita Von Teese

Woman in a pink mesh lingerie set with embroidered flowers and matching gloves, posed in a vintage vanity room with ornate wood furnishings. Close-up highlights her retro curls, red lips, and dramatic earrings.
Image via @DitaVonTeese on X

Dita Von Teese, the burlesque performer and model, basically asked, “What if the 1940s never ended?” and then built an entire career on it. Corsets, finger waves, and waistlines so tiny they could cut glass.

Her 2005 Vivienne Westwood wedding gown? Purple, massive, and aggressively theatrical. Minimalist brides wept while Dita glided down the aisle looking like a Hollywood empress resurrected for one last close-up.

“Heels and red lipstick will put the fear of God into people,” she once joked. Von Teese proves rhinestones and eyeliner can still strike terror—and admiration—in equal measure.

45. Linda Evangelista

Model on a dimly lit runway in a dramatic mermaid gown with a beaded corset bodice and voluminous feathery skirt, styled with platinum white hair. Close-up captures her icy makeup and sculptural neckline.
Image via u/ChicnahueCoatl1491 on Reddit

Linda Evangelista wasn’t just a model; she was the CEO of her own face. She could reinvent herself with a haircut and launch a thousand trends before lunch.

Her legendary quote—“I don’t get out of bed for less than $10,000 a day”—wasn’t a complaint; she just knew her worth than the rest of us. Linda basically unionized the runway with a single sentence.

She stands as fashion’s ultimate negotiator: flawless, sarcastic, and proof that beauty may fade, but a killer one-liner lasts forever.

44. Tom Ford

Man in a black velvet suit jacket with a checkered silk scarf tied at the neck, posing indoors with a suave demeanor. Close-up reveals his tailored grooming and sharply styled beard.
Image via @TOMFORD on X

Tom Ford rescued Gucci in the ’90s with velvet suits so sexy they probably needed warning labels. Then he started dressing himself like James Bond just to prove he could.

His 2004 exit from Gucci was treated like a global crisis—Wall Street worried, editors wept, and Ford just moved on to directing films because apparently one empire wasn’t enough.

“I probably do have an obsessive personality,” he once admitted. He reminds us that being overdressed is never a flaw—unless you’re standing next to him. Then it’s just cruel.

43. Erykah Badu

Woman on a red carpet in a forest green gown with yellow accents and a tall green headwrap, holding yellow flowers and wearing metallic gloves. Close-up shows her natural glow and confident smile.
Image via thecut on Pinterest

Erykah Badu, the singer and songwriter often dubbed the “Queen of Neo-Soul,” treats every public appearance like performance art. Remember the giant headwraps? The hats wider than small apartments? She doesn’t wear outfits—she builds architectural monuments out of fabric.

Her fearless Afrofuturist style has influenced designers from Rick Owens to Pyer Moss. When she showed up to the 2014 Met Gala in towering headgear, she didn’t just turn heads… she blocked sightlines. No one ever complained. Because why?

“They call me weird, I call me limitless,” she once said. Badu proves that fashion is best when it’s at least a little inconvenient for everyone around you.

42. Brigitte Bardot

Woman sitting on stone steps in a long grey wool skirt, white blouse, and oversized polka dot necktie with a black bow in her voluminous blonde hair. Close-up highlights her winged eyeliner and classic pout.
Images via animationavenue and vincevance on Pinterest

The French screen legend and model Brigitte Bardot turned ballet flats, messy hair, and off-the-shoulder tops into weapons of mass seduction. She didn’t need couture—she made vacation wear in Saint-Tropez look like world domination.

Her gingham wedding dress in 1959 launched copycats everywhere, proving you don’t need silk or diamonds to be unforgettable—sometimes all it takes is a picnic pattern and confidence.

Bardot shows that effortless chic is often just effort, very well disguised. After all, not everyone can make eyeliner and tousled bangs look like a global aesthetic.

41. Mick Jagger

Man mid-performance wearing a red crop top and vibrant color-blocked leggings in red, yellow, and blue while singing into a microphone on stage. Close-up captures his expressive face and animated hand gesture.
Image via r/rollingstones on Reddit

Mick Jagger strutted across stages in ruffled shirts, velvet pants, and body suits so tight they could double as second skin. He made androgyny look like pure rock-and-roll testosterone.

From sequined jumpsuits to leopard-print coats, his wardrobe told men everywhere that subtlety is boring. The Rolling Stones weren’t just a band—they were a traveling runway with guitars.

Jagger proves that fashion doesn’t just belong to runways or royalty. Sometimes it belongs to sweaty arenas, bad lighting, and a man in eyeliner who still steals your girlfriend.

40. Jackie Collins

Woman at a red carpet event wearing a black jacket with leopard-print top and star pendant necklace, smiling amid a crowd. Close-up shows her voluminous hair and bold eye makeup.
Image via Pinterest

Ranked 40 on our list, Jackie Collins didn’t just write about scandal—she dressed like she was always attending the afterparty. Sequins, cleavage, and jewelry the size of small countries became her professional uniform.

Her heroines—Lucky Santangelo most of all—were basically Jackie in novel form: glamorous, ruthless, and impeccably dressed. Collins blurred the line between fiction and wardrobe, and readers loved every sparkly minute.

“My heroines kick ass. They wear heels and lipstick but they kick ass,” she said. She reminds us that fashion isn’t just about clothes—it’s about character development.

39. Diana Vreeland

Elderly woman walking confidently in a metallic brocade coatdress with a black velvet lapel and gloves, set against a vivid abstract red and orange backdrop. Close-up highlights her slicked-back hair, subtle earrings, and composed expression.
Image via alfredstephen on Pinterest

Diana Vreeland didn’t just edit magazines; she declared cultural law. At Harper’s Bazaar, her “Why Don’t You…?” column suggested things like washing your child’s hair in champagne. Ridiculous? Yes. And memorable.

At Vogue, she turned fashion spreads into full-blown fantasies—exotic locations, surreal styling, and drama that made readers want to buy couture they couldn’t pronounce. Vreeland made imagination mandatory.

Her motto? “Elegance is refusal.” Translation: saying no is just as fashionable as saying yes. Editors since have been trying to copy her, but few do it with champagne.

38. Gisele Bündchen

Model strutting down a runway in a black and white polka dot bikini top and matching pants, carrying a coordinating tote. Second image highlights her beachy waves and confident walk.
Images via goldenfilmz and tandcmag on Pinterest

Gisele Bündchen arrived in the late ’90s and stomped out heroin chic with a single flip of her hair. Suddenly, curves, tans, and beach waves were back on the runway.

Her Victoria’s Secret years basically turned the annual show into the Super Bowl of lingerie. She made angel wings iconic enough to require their own insurance plan.

She once said, “I’m not a model. I am just me.” Coming from a woman who once made $45 million in a single year, that’s the most casual flex ever.

37. Pharrell Williams

Man at a formal event wearing a textured double-breasted white blazer with wide-leg black pants, black tie, and dark sunglasses. Close-up shows a calm expression and sharp tailoring.
Image via u/skermahger on Reddit

Pharrell wore a hat so enormous at the 2014 Grammys it got its own Twitter account. That’s influence: turning a Vivienne Westwood accessory into internet celebrity.

From Billionaire Boys Club to Adidas collaborations, Pharrell blurred the line between streetwear and luxury long before fashion houses figured out sneakers could cost $800. Now, he’s steering Louis Vuitton menswear.

“I love everything that’s old, everything that’s retro,” he said. Somehow, he’s made retro look futuristic. Few people could sell both oversized hats and monogrammed trunks with equal conviction.

36. Sophia Loren

Woman walking through a crowded space in a white blouse with balloon sleeves and a colorful floral scarf, accessorized with oversized eyeglasses and a plaid pencil skirt. Close-up captures her polished hair and dramatic eyewear.
Image via popsugar on Pinterest

The Italian film star Sophia Loren could walk into a room in a plain black dress and still make every jewel-encrusted gown around her look like an afterthought. That’s called presence.

Her signature hourglass silhouettes and plunging necklines defined Italian cinema glamour. In the 1960s, her dresses influenced fashion houses across Europe, all desperate to bottle whatever made Loren magnetic.

“I’d rather eat pasta and drink wine than be a size zero,” she famously said. Loren was lowkey saying you can be glamorous and carb-friendly—a revolutionary stance in fashion.

35. Harry Styles

Man standing in an open grassy field wearing a light blue ruffled gown paired with a black tailored blazer. Close-up shows his relaxed stance and natural makeup, blending masculine and feminine style.
Image via @TheHarryNews on X

Harry Styles doesn’t just wear clothes; he creates debates. From pearl necklaces to Gucci gowns on the cover of Vogue, he made dressing fluid feel like a natural evolution, not a gimmick.

His stage costumes—sequined jumpsuits, feather boas, sheer shirts—have become part of his fandom’s language. Fans don’t just attend concerts; they coordinate outfits as if they’re auditioning for Harry’s band.

“Clothes are there to have fun with,” he told Vogue. It’s simple, but it works. Styles has made joy itself look like fashion’s most radical accessory.

34. Marlene Dietrich

Woman confidently walking down a tree-lined street in a tailored tan suit and maroon beret, with a black turtleneck underneath. Close-up captures her bold red lipstick and structured styling.
Image via u/Oneiricroad on Reddit

Marlene Dietrich made tuxedos sexy for women decades before Yves Saint Laurent thought of Le Smoking. She’d strut into parties in top hats and bow ties while everyone else looked like wallpaper.

Her 1930 film Morocco featured her kissing a woman in full tuxedo—a scene so shocking for the era it’s still referenced today. Dietrich didn’t bend gender rules; she broke them. Because why not?

“I am at heart a gentleman,” she once said. Dietrich showed the world that tailoring and attitude are sometimes the sharpest accessories a woman can own.

33. Elizabeth Taylor

Young woman twirling in a deep red velvet dress and black heels in an ornate vintage living room, with framed artwork and a carved fireplace behind her. Close-up highlights her youthful beauty and confident pose.
Image via picmagik on Pinterest

Elizabeth Taylor’s jewelry collection had its own fan base. The 69-carat Taylor-Burton diamond? Casual wedding gift. The Krupp diamond? Tuesday. She wore gems the way most of us wear SPF.

Her fashion sense leaned toward big hair, plunging gowns, and color so bold it practically yelled at you from across the room. Nobody ever accused Taylor of subtlety.

“I adore wearing gems,” she said. “But not because they are mine. You can’t possess radiance, you can only admire it.” But wasn’t she radiant, though? And terrifyingly quotable.

32. Miuccia Prada

Woman smiling while standing in a white button-up shirt tucked into a black leather skirt with a light sweater tied over her shoulders. Close-up captures her natural makeup and relaxed elegance.
Image via wwd on Pinterest

Miuccia Prada inherited her family’s luggage business and promptly turned it into a temple of intellectual fashion. Nylon handbags? Once boring, now the uniform of editors who read Deleuze between shows.

Her collections mix ugly-pretty aesthetics with razor-sharp tailoring. She pioneered the idea that you don’t have to look “beautiful” in the conventional sense to look cutting-edge. Nerdy is couture now.

Prada once said, “What you wear is how you present yourself to the world.” Coming from her, that sounds less like advice and more like a politely disguised critique.

31. Heidi Klum

Woman posing on the Emmys red carpet in a shimmering silver gown with one long sleeve, side cutout, and a high slit, wearing strappy heels and sleek straight hair. Close-up shows her radiant makeup and diamond accessories.
Image via jocostan and adilaalatas on Pinterest

Heidi Klum went from Victoria’s Secret Angel to Project Runway judge, turning “auf Wiedersehen” into fashion’s most ominous goodbye. She didn’t just model fashion; she built an empire critiquing it.

Her Halloween costumes alone deserve recognition—whether as a worm, an alien, or Jessica Rabbit, Klum commits harder than half the Met Gala guest list. Everyone waits for her to show up.

“I believe you have to be comfortable in your skin,” Klum said. Which is ironic considering she once glued prosthetic veins all over it for a party.

30. Iman

Woman standing barefoot on the beach in a voluminous pleated ivory gown with silver embellishments and oversized earrings. Close-up shows her serene gaze under a clear blue sky.
Image via @The_Real_IMAN on X

The Somali supermodel Iman stepped onto the runway in the 1970s, and Yves Saint Laurent instantly called her his “dream woman.” Not surprised! Designers everywhere lost their collective minds over her regal beauty and commanding presence.

But she didn’t just model. With IMAN Cosmetics, she became a pioneer in inclusive beauty, offering shades for women of color long before brands realized diversity wasn’t optional.

Here, cracking the thirties, Iman reminds us that real influence isn’t just about walking runways—it’s about changing the entire industry so others can walk behind you. Her personal life later intertwined with another legend on this list, creating one of fashion’s most iconic power couples!

29. Kanye West

Man with platinum blonde hair walks down a wet street in a loose tan windbreaker, dark joggers, and chunky black boots, wearing a thick silver chain. Close-up highlights his serious expression.
Image via r/Kanye on Reddit

Say what you will about Kanye West—sorry, but he dragged hoodies and sneakers onto runways that once only tolerated silk gowns. Yeezy sneakers turned resale markets into Wall Street for hypebeasts.

His 2009 outburst at Taylor Swift is infamous, but in fashion, it’s the beige sweatsuits and dystopian sneakers that echo. Whether you loved or hated them, you noticed.

Ye once said, “I am Warhol. I am the number one most impactful artist of our generation.” Subtlety isn’t his thing, but influence? Absolutely undeniable.

28. Grace Kelly

Woman in a mint green satin gown with draped waist and train stands gracefully against a neutral background. Second image features her serene expression and softly curled blonde hair.
Image via @aemisias on X

The American film star turned princess, Grace Kelly, set an eternal bridal standard with her 1956 wedding gown. 60 years later, Kate Middleton essentially cosplayed the look, proving timeless style never requires reinvention.

Kelly’s off-duty chic—capri pants, knotted shirts, and scarves—helped define casual European glamour. She could make grocery shopping look like a Vogue editorial. Monaco was just lucky to claim her.

“She had a kind of serenity,” Hubert de Givenchy once said. That serenity was apparently strong enough to keep lace bodices in bridal fashion for half a century and counting.

27. Elsa Schiaparelli

Woman in a structured blazer and dark dress sits on a couch wearing a tilted wide-brimmed hat and brooch, with legs crossed. Close-up shows her serious expression and elegant pearl necklace.
Images via voguebrasil and adilaalatas on Pinterest

Elsa Schiaparelli collaborated with Salvador Dalí, turning lobsters, skeletons, and desk drawers into couture. Her designs were less clothing and more conversation starters—assuming your dinner party tolerated surrealist humor.

Her shocking pink became a fashion signature, inspiring countless designers who still haven’t managed to make magenta look this chic. She was weird before weird was profitable.

Schiaparelli once said, “In difficult times, fashion is always outrageous.” Coming from a woman who put a shoe on someone’s head as a hat, it feels like understatement.

26. Cindy Crawford

Woman walking outdoors in a sleeveless light blue pencil dress with silver belt and buttons, accessorized with heels and sunglasses. Close-up captures her voluminous hair and classic elegance.
Image via @MichaelKors on X

Cindy Crawford’s 1992 Pepsi commercial in cutoff shorts and a white tank didn’t just sell soda—it sold the idea that supermodels were the new rock stars.

Her mole became her trademark, proving a beauty mark could be worth millions. In the ’90s, her runway strut defined glamour alongside Naomi Campbell, Christy Turlington, and Claudia Schiffer—supermodel royalties in full display.

“I don’t try to pretend to be someone I’m not,” Crawford firmly holds the idea, which is easy when “yourself” is synonymous with America’s collective definition of beauty.

25. Jacqueline Kennedy

Woman descending airplane steps in a pink Chanel-style suit with matching pillbox hat and white gloves, later seen smiling with a bouquet of red roses. Second image captures her poised expression and timeless look.
Image via tunocSama on Pinterest

Jackie Kennedy didn’t just bring style to the White House—she staged a masterclass in diplomacy via pillbox hats and chic pastel suits. Political influence, but make it couture.

Her pink Chanel suit on the day of JFK’s assassination became both iconic and tragic, a symbol of elegance colliding with history’s darkest moment. She wore it with stoic grace.

“Pearls are always appropriate,” Jackie said. Appropriately, so is she—still a reference point for First Lady fashion, decades after she left the White House.

24. Beyoncé

Woman in a glittering canary yellow long-sleeve gown with a high neckline and body-hugging silhouette, standing against a dark background. Second image highlights her bold earrings, sleek ponytail, and red lips.
Image via @TheFashionCourt on X

Beyoncé doesn’t wear clothes; she wears declarations. Her 2018 Coachella performance in Balmain wasn’t just a concert—it was a cultural reset with sequins. Every outfit reinforced the message: she’s running the world.

From Givenchy gowns at the Met Gala to Ivy Park’s athletic empire, Beyoncé bridges haute couture and athleisure without breaking a sweat. She could probably sell bedazzled sweatpants as power suits.

“Your self-worth is determined by you,” she told Elle. And judging by her wardrobe, her self-worth is somewhere between “regal deity” and “force of nature.”

23. Alexander McQueen

Man mid-air in a joyful leap wearing traditional Scottish Highland attire including a tartan kilt, sash, and feathered cap, with an animated expression. Close-up captures his playful personality.
Image via GottaHaveBalls on Pinterest

Alexander McQueen turned runways into nightmares you couldn’t look away from. Holograms of Kate Moss, spray-painted dresses, and skull motifs proved fashion could be both art gallery and haunted house.

His tailoring was razor-sharp, his imagination darker still. McQueen’s shows weren’t designed for Instagram—they were designed to shock live audiences into awe, confusion, or occasionally tears.

“I want to empower women. I want people to be afraid of the women I dress,” he once said. Honestly, mission accomplished. His fashion angels would likely step on you.

22. Marilyn Monroe

Iconic black and white image of a woman in a white halter-neck pleated dress caught mid-air over a subway grate, holding it down with a playful smile. Close-up highlights her classic blonde curls, winged eyeliner, and glamorous expression.
Image via Wikimedia Commons

Marilyn Monroe could make a potato sack look sultry, and in fact, she once literally did for a photoshoot. Even burlap surrendered under her charm.

Her white halter dress from The Seven Year Itch remains one of cinema’s most recognizable images—part wardrobe, part wind machine, entirely iconic.

“Give a girl the right shoes and she can conquer the world.” For Marilyn, conquering often involved stilettos, diamonds, and an audience.

21. Lady Gaga

Woman posing on the red carpet in a dress, boots, and headpiece made entirely of raw meat, with pastel lavender and blue hair and shimmering diamond jewelry. Close-up captures her confident stare and bold red lip.
Image via jayk0448 on Pinterest

Lady Gaga wore a raw meat dress to the 2010 VMAs, and suddenly everyone at home was Googling, “Is this hygienic?” Few pop stars weaponize fashion quite like Gaga.

From McQueen armadillo heels to her Valentino ballgown at the 2019 Oscars, she’s proven she can pivot from shock value to classic glamour without losing credibility—or fans.

“You have to be unique, and different, and shine in your own way,” Gaga says no to subtlety. Remember always: don’t be a drag, just be a queen.

20. Jean Paul Gaultier

Man with bleached hair and a mischievous smile wears a blue-and-white striped top and black kilt, lifting one leg over a bench while holding a cocktail glass. Whimsical background features stars, buildings, and circus elements.
Image via wmag on Pinterest

Jean Paul Gaultier’s 1990 cone bra for Madonna’s Blonde Ambition tour may be the single most famous undergarment in history. It made lingerie outerwear, long before Instagram tried the same trick.

He sent men down runways in skirts, embraced tattoos and piercings, and celebrated unconventional beauty decades before the industry caught up. Shock was no longer a gimmick; it was his brand identity.

Here, entering our top 20, Gaultier reminds us that fashion isn’t about fitting in. It’s about corseting society itself until it shifts—sometimes uncomfortably—in a new direction.

19. Giorgio Armani

Older man in a monochrome navy outfit with belted shorts, loafers, and a sweater tied around his shoulders, speaking on a chunky 90s-style mobile phone. He wears round sunglasses and a silver watch, standing confidently in a European plaza with people in the background.
Image via All Blues Co. on Facebook

Giorgio Armani made power dressing sleek. His unstructured jackets in the 1980s softened stiff tailoring and basically fueled an entire decade of Wall Street confidence and Hollywood suiting.

Richard Gere in American Gigolo put Armani on the map. From then on, Armani wasn’t just a label—it was shorthand for “I can afford a personal driver.”

We’ve just heard that on September 4, 2025, Armani passed away peacefully at home in Milan at the age of 91, surrounded by loved ones. Armani’s legacy echoes his own dictum: “Elegance is not about being noticed, it’s about being remembered.” And he certainly will be.

18. Twiggy

Model wearing a bright yellow skirt suit with a bold floral tie poses in front of a deep purple backdrop. Second image zooms in on her iconic short hair and wide-eyed expression.
Image via @Twiggy on X

Twiggy’s pixie haircut and wide eyes turned her into the first super model of the swinging ’60s. Suddenly, teenagers had a fashion figure who wasn’t trying to look forty.

Her androgynous, skinny silhouette sparked headlines and debates but also made her the face of London’s Mod movement. Mary Quant’s miniskirts never looked the same once Twiggy wore them.

She argued that, “Being young isn’t about age, it’s about being a free spirit.” And she embodied it—complete with eyeliner thick enough to double as war paint.

17. Cher

Woman on stage in a bold 70s ensemble with a fringed crop top and colorful floral bell-bottom pants, holding cue cards with long dark hair flowing. Second image shows her focused expression under stage lighting.
Image via u/SagaciousStream on Reddit

Cher’s Bob Mackie gowns basically invented “naked dresses” long before Instagram influencers called them edgy. Sequins, feathers, and cutouts? Tuesday. She wore Oscar’s wildest outfits like other people wear khakis.

The 1986 Oscars saw her in a towering feather headdress that made Vegas jealous. Cher didn’t attend ceremonies—she disrupted them.

“Until you’re ready to look foolish, you’ll never have the possibility of being great,” she advised. Dress like you might be ridiculed, and congratulations, you’re a Cher moment.

16. Vivienne Westwood

Elderly woman seated at a dinner event wearing a ruffled jacket with blue floral trim and a cameo brooch, paired with striped red and gold skirt. Second image captures her soft smile and hand gently resting on her neck.
Image via wwd on Pinterest

Vivienne Westwood sold bondage trousers and safety pins in the ’70s and somehow turned them into haute couture. The establishment clutched its pearls—she used them as brooches.

Her tartan collections, corsets, and anarchic runway shows cemented her as fashion’s most gleeful rebel. Without Westwood, punk might’ve stayed in basements instead of strutting through Paris.

For her, “You have a more interesting life if you wear impressive clothes.” In Westwood’s vocabulary, “interesting” usually meant scandalous, political, and unforgettable.

15. Kate Moss

Model with voluminous tousled hair and pearl earrings poses in a corset-inspired off-white gown with subtle stripes, hands on hips. Close-up highlights her striking makeup and confident expression.
Image via 1hyacinthe1 on Pinterest

Kate Moss made grunge look chic when everyone else was still hung up on glamour. Her Calvin Klein ads with Mark Wahlberg redefined minimalism and, let’s be honest, sold a lot of underwear.

Her skinny, waifish look sparked global controversy and the “heroin chic” label, but Moss outlasted critics with a career that kept her at fashion’s center for decades.

“Never complain, never explain,” she famously said, which is precisely how you survive scandals, slip-ups, and being photographed in every bar in London.

14. Grace Jones

Woman with a sculpted high-top fade haircut and exaggerated shoulders wears a sharp black blazer with a cigarette held dramatically between her lips. Second image stylizes her with a minimalist beige backdrop and stark lighting.
Image via @thejpgvibe on X

Grace Jones walked into the 1980s like fashion was her personal playground. Suits, body paint, sculptural haircuts—she didn’t wear trends, she demolished them and built new ones from the rubble.

Her partnership with Jean-Paul Goude gave us some of the most striking images in fashion history: Jones as a panther, Jones as a statue, Jones as basically a one-woman genre.

“I go through styles like people go through underwear.” Fashion wasn’t just a phase for Jones; it was a full-time job description.

13. Rihanna

Woman wearing a dramatic oversized black hat and structured pinstripe gown with a cropped jacket, accessorized with layered polka-dot neckties and brooch. Close-up captures her bold lip and confident gaze.
Image via @TheNerdsofColor on X

Rihanna went from “Umbrella” to umbrella brand. Savage X Fenty shows didn’t just rival Victoria’s Secret—they buried it with body diversity, choreography, and lingerie that actually looked wearable.

Her 2015 Met Gala gown, a massive yellow Guo Pei creation with a train so big it needed GPS, is now meme legend: “omelet dress,” but make it couture.

Rihanna jokingly said, “She can beat me, but she cannot beat my outfit.” Hard to argue with a mogul who turned her wardrobe into a billion-dollar empire.

12. Gianni Versace

Seated man wearing a colorful silk shirt with Greek key trim and bold prints, paired with black jeans and gold accessories. Close-up shows his composed expression and luxurious surroundings.
Image via nick_goodey on Pinterest

Gianni Versace made Miami glam a global export. Baroque prints, neon colors, and safety-pin gowns weren’t just fashion—they were Versace signatures. He basically turned excess into elegance.

His runways created the “supermodel moment”: Naomi, Cindy, Linda, and Christy strutting arm in arm to George Michael’s “Freedom!” It was fashion as spectacle, and it hasn’t been topped.

Gianni claimed, “In the past, people were born royal. Nowadays, royalty comes from what you do.” He crowned celebrities with sequins, and they never took the crowns off.

11. Donatella Versace

Woman in a plunging green jungle-print gown with a thigh-high slit and long straight platinum hair, smiling as she walks past a crowd and photographers. Second image shows a close-up of her dewy skin and bold smoky eyes.
The Green Dress. (Image via legallybrunette92 on Pinterest)

Donatella Versace stepped into her brother’s shoes after his tragic death in 1997 and somehow kept the house’s drama intact. Platinum hair and smoky eyeliner became part of the brand DNA.

Her biggest mic-drop moment? Jennifer Lopez’s plunging green jungle dress at the 2000 Grammys. It was so outrageous it inspired Google to invent Google Images! Talking about influence.

“I don’t like balance. Balance is not a word you can use in fashion,” Donatella hit at her critics. Safe to say she’s been keeping Versace deliciously unbalanced ever since.

10. Princess Diana

Smiling woman in an off-the-shoulder black dress with sheer black tights and a statement choker necklace, walking across a grassy lawn. Second image captures her joyful expression and elegant jewelry.
Image via u/DebateObjective2787 on Reddit

Princess Diana’s style evolution—from frilly ’80s gowns to sleek ’90s minimalism—made her a global icon. She didn’t just wear clothes; she communicated her independence and rebellion through every hemline.

Her 1994 “revenge dress”—a slinky, off-the-shoulder Christina Stambolian number—wasn’t just fashion, it was a statement: Hey, cameras here. While Charles confessed to infidelity, Diana silently stole the news cycle in chiffon and heels.

Entering the top ten, Diana proves fashion can speak louder than crowns. She didn’t just redefine royal fashion—she made it personal, vulnerable, and impossibly powerful.

9. Madonna

Woman lies on satin sheets in a white lace bustier with long gloves and layered jewelry, styled like a bridal look. Her voluminous hair and dramatic makeup amplify the retro glam aesthetic.
Image via carlymcgrellis on Pinterest

Madonna didn’t just wear trends—she invented them, then abandoned them before anyone else caught up. Lace gloves, cone bras, crucifix jewelry—she made controversy fashionable long before Instagram discovered “shock value.”

Her 1990 Blonde Ambition tour, styled by Jean Paul Gaultier, gave us the cone bra that changed both lingerie and stagewear forever. She made fashion part of her performance vocabulary.

“I am my own experiment. I am my own work of art,” Madonna refused to adhere to society’s standards. Few artists have turned self-reinvention into such a long-running, bestselling franchise.

8. David Bowie

Man with bright red hair wearing a vivid yellow suit over a striped shirt sits with a cigarette and scissors in hand. Second image zooms in on his intense gaze and vibrant outfit.
Image via expresswebsite on Pinterest

David Bowie treated his wardrobe like another instrument. From Ziggy Stardust’s metallic jumpsuits to the Thin White Duke’s sharp tailoring, Bowie showed masculinity could be as fluid as his music.

His 1972 appearance on Top of the Pops in a quilted jumpsuit, draping an arm around Mick Ronson, scandalized and electrified Britain. The moment still defines glam rock.

Offstage, his marriage to supermodel Iman fused two icons into one of fashion’s most magnetic unions. “I don’t know where I’m going from here, but I promise it won’t be boring,” Bowie vowed—and neither was their life together.

7. Yves Saint Laurent

Stylish man wearing a black satin shirt and high-waisted trousers leans against a column, with layered silk scarves tied at the neck. Close-up reveals large glasses and tousled hair.
Image via yokomae on Pinterest

When Yves Saint Laurent debuted Le Smoking tuxedo for women in 1966, the fashion world gasped. Finally, women can wear what men wear and make it even better.

Beyond tuxedos, he revolutionized ready-to-wear, making designer fashion accessible outside couture salons. He made “off the rack” sound chic instead of tragic.

“Chanel freed women, and I empowered them,” he proudly said. Confidence in tailoring, indeed. Saint Laurent turned clothing into cultural politics—and made it look good.

6. Christian Dior

Tailor or designer adjusting the sleeve of an elegant lavender gown worn by a poised model, with colorful fabric rolls stacked behind them. Second image captures his focused expression.
Image via fabricsstore on Pinterest

Christian Dior’s 1947 “New Look” was an explosion of fabric after wartime rationing—tiny waists, full skirts, and a return to ultra-femininity that shocked postwar Paris back into indulgence.

The silhouettes became instantly iconic, though not without backlash: women burned corsets for a reason, and Dior unapologetically cinched them back in. Still, the style dominated the 1950s.

“I wanted my dresses to be constructed, molded upon the curves of the female body,” Dior said. He built architecture out of silk, and the world lined up for tickets.

5. Audrey Hepburn

Young woman sitting on grass by a riverbank in a red cardigan and striped pants, with matching red shoes and bows. The second image shows her smiling gently with trees in the background.
Image via WhoWhatWear on Pinterest

Audrey Hepburn’s Givenchy gown in Breakfast at Tiffany’s didn’t just dress Holly Golightly—it made the little black dress immortal. One movie outfit, a century of cocktail parties forever transformed.

Her ballet flats, slim pants, and gamine haircut made her an accessible style icon. Audrey proved fashion didn’t need glitter to dazzle—sometimes it just needed pearls and good posture.

“Elegance is the only beauty that never fades,” she said. Sitting in the top five, Hepburn’s elegance hasn’t faded either. Black dresses and oversized sunglasses still owe her royalties.

4. Naomi Campbell

Model in a gold, heavily embellished crop top and fitted pants poses dramatically against a wall, with ornate accessories and a high updo. The second photo focuses on her regal expression and gold detailing.
Image via @artdelacouture on X

You hear the word runway, and all you can think about is the name: Naomi Campbell. The woman who owned it. Her strut was so fierce that competitors just stayed out of the way. Not only that, designers prayed she’d open their shows.

She broke barriers as one of the first Black supermodels to dominate the ’90s, while also headlining Versace, Dior, and Vivienne Westwood. Remember her 1993 Westwood runway fall? Even that became iconic.

“I never diet. I smoke and I drink now and then. I never suffer,” she bragged. Proof that attitude, not abs, can make you immortal. Well, maybe if you’re Naomi Campbell. But what if you’re not?

3. Karl Lagerfeld

Older man with white hair and dark sunglasses walking a runway in a layered navy outfit, including a long coat, high-collared shirt, and chains. The second shot is a close-up capturing his confident expression.
Image via thecut on Pinterest

Karl Lagerfeld made ponytails and sunglasses a corporate logo. At Chanel, he turned tweed suits into pop culture currency and once staged a full-size supermarket for a runway show, just because he could.

He didn’t just design clothes—he engineered events. Chanel runways became cinematic universes: icebergs, rocket launches, beaches, you name it. Fashion wasn’t seasonal with Karl, it was theatrical.

“Sweatpants are a sign of defeat,” he declared. Harsh, but very Karl. He made couture global again, while simultaneously making everyone question their loungewear choices.

2. Anna Wintour

Woman in a long powder-blue coat over an embroidered silver gown standing confidently among a crowd. Close-up image highlights her precise bob haircut and soft makeup.
Image via u/skermahger on Reddit

Anna Wintour’s bob and sunglasses could silence a room faster than a fire alarm. At Vogue, she transformed the magazine into a cultural juggernaut, dictating not just fashion trends but cultural conversation.

She inspired The Devil Wears Prada’s Miranda Priestly, though Wintour played it cool, even attending the premiere in Prada. The book may have been satire, but the icy reputation? Untouchable brand strategy.

“Create your own style. Let it be unique for yourself and yet identifiable for others,” she advised. A nod of approval from her can launch a designer overnight, while silence from her front row seat might as well be a death sentence. Wintour nearly took the crown—but power still bowed to a woman who started it all.

1. Coco Chanel

Elderly woman seated in a high-back chair, wearing layered pearl necklaces, a beige suit, and a red blouse, smiling warmly. In the second image, she’s seen closer-up, showing her expressive face and signature style.
Image via Refinery29au on Pinterest

Claiming the top spot of our list is Coco Chanel, whose impact on fashion is nothing short of seismic. She didn’t just design clothes—she rewrote the dictionary of femininity. The little black dress of 1926 wasn’t just chic; it was liberation disguised as eveningwear.

Her tweed suits freed women from corsets, her quilted handbags became eternal, and her pearls made costume jewelry respectable. Chanel wasn’t following fashion—she was dictating how women could live inside it.

“Luxury must be comfortable, otherwise it is not luxury,” she once said. Nobody does it like Coco. She was fashion’s Big Bang! Without her, there is no Saint Laurent, no Dior, no modern style. Period.

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