20 Most Iconic Designer Shoes of All Time

From magical slippers to sophisticated stilettos, a look at the shoes that have kept the fashion world enthralled and in step.

“To wear dreams on one’s feet is to begin to give a reality to one’s dreams,” said legendary shoe designer Roger Vivier. Such is the transformative power of shoes, able to turn us into princesses, or take us where we want to go even if it’s just to go home. Gorgeous footwear finishes off a look with flair and gives you that extra bit of confidence so you can strut to your goals in style. Here, Town&Country takes a look at the most memorable pairs—from the pumps that got Carrie Bradshaw to say ‘I Do,’ to the platforms that caused Naomi Campbell to topple over, and to the ones fashion royalty and actual royalty can’t live without. 

Famous Shoes on Film

There’s nothing like a great pair of shoes to get us in the mood, be it to fall in love or to conquer the world and these film favorites definitely deserve their icon status.

1. Dorothy’s Ruby Red Slippers


Few shoes are as memorable as Dorothy Gale’s ruby slippers from the landmark technicolor film The Wizard of Oz. Played by Judy Garland, the little girl from Kansas traversed the yellow brick road in these crimson stunners, which were designed by MGM costume designer Gilbert Adrian. While accounts vary, some say around five to ten pairs were made for the film, one of which is housed in the Smithsonian Museum. Each made with 2,300 sequins on a base of silk, they are some of the most cherished pieces of film memorabilia. But perhaps makes it so special is how they made us believe in magic, that with three clicks and a whole lot of gumption, we can achieve anything our hearts desire.

2. Carrie Bradshaw’s ‘Something Blue’ Heels

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The #ManoloWeddingWednesday season is back! Today we are featuring this picture by the beautiful @peonylim #Hangisi

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There was a collective gasp heard all over the world when Mr. Big got down on one knee, and proposed to the quintessentially single New Yorker Carrie Bradshaw with the most gorgeous pair of sapphire satin heels. That he did it in their walk-in shoe closet makes the moment even more epic. That royal blue pair we all ogled over is none other than Manolo Blahnik’s Hangisi pumps, which Carrie later wore to her much simpler civil wedding in the Sex and the City movie. It’s something of a legend now, with brides including fashionista Olivia Palermo, wearing it to say their own vows.

3. Cinderella’s Glass Slippers

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If there ever was a pair that captured our imaginations, it would be that of Cinderella’s mythical glass slippers and the fairy tale romance it has come to represent. The shoe’s scintillating resilience despite its obvious fragility has come to symbolize how good triumphs over evil despite the direst of circumstances, and has made many a young girl dream of serendipitous meet-cutes for generations. For the 2015 movie, costume designer Sandy Powell collaborated with Swarovski to create the crystalline sparklers we see onscreen. Eight versions of the glass shoe were made (in various levels of breakability), which were then with the help of movie magic transposed onto Lily James’ beautiful feet.

4. Marie Antoinette’s Manolo Blahniks


It could be quite a sartorial mystery trying to figure what Marie Antoinette would wear or who she’d commission to make her shoes, but it was something director Sofia Coppola knew right off the bat. "She would've asked Manolo." For the 2006 biographical film starring Kirsten Dunst, the shoe designer looked at pictures of the French queen’s footwear for inspiration. He created hundreds of gorgeous beribboned pieces, bringing to life the rococo aesthetic with an elegant modernity for the film. The decadent masterpiece would go on to win Best in Costume at the 2007 Oscars.

5. Andy Sach’s Chanel Boots

As far as style transformations go, there’s very little that can top Andy Sach’s jaw-dropping turn from clueless assistant to the ultimate fashion girl in The Devil Wears Prada. And just as she was being written off her Runway colleagues (played Emily Blunt and Gisele Bundchen) Anne Hathaway enters full of confidence in head-to-toe designer regalia. The cherry on top was of course those thigh-high Chanel cuissarde leather boots. Supple, sexy, and unmistakably cutting edge, they made our beloved protagonist look like she, as they say, just stepped off her very own runway.


6. Catherine Deneuve’s Roger Vivier Pilgrim Pumps

Worn by Catherine Deneuve in the surreal film Belle du Jour, Roger Vivier’s pumps with their unmistakable silver buckle have become the stuff of legend. Deneuve captivated audiences with her hauntingly beautiful performance as a bourgeoise housewife by day, hiding a clandestine life as a modern-day courtesan in the afternoons. Her costumes as Severine consisted of a slew of beautiful Yves Saint Laurent coats and dresses and of course the patent leather “Belle Vivier” pumps. The classically elegant silhouette of this shoe was perfect for when she was prim, polished, and proper, keeping her secret tenuously under the surface. It is perhaps Vivier’s ability to convey both covert sexiness and ladylike sensibilities that have given this shoe, and many of his other designs, its enduring appeal.

7. Cher Horowitz’s Mary Janes 

Who could forget the charming antics of our favorite poor little rich girl, Cher Horowitz in Clueless? An heiress with a gold heart, Alicia Silverstone’s character exemplified the best of nineties fashion, replete with mini dresses, Alaia, and of course her trademark Mary Janes. The schoolgirl-inspired shoe finished off all her looks with flair, inspiring an entire generation to follow suit. And with fashion having a proper retro moment, don’t be surprised to see modern iterations of this preppy classic popping up on many an influencer’s feet.

Shoes that Defy Gravity 

Extreme heels have long been a part of history, some fashioned out of necessity, and others borne of the whims of fashion. Here we take a look at our favorites of these vertigo-inducing stunners.  


8. Alexander McQueen’s Armadillo Boots

“[This collection predicted a future in which] the ice cap would melt… the waters would rise and… life on earth would have to evolve in order to live beneath the sea once more or perish. Humanity [would] go back to the place from whence it came,” the late Alexander McQueen said of his final show entitled “Plato’s Atlantis” (Spring/Summer 2010) from which the inimitable Armadillo boot would emerge from. (3) Quite a prescient notion one would think, given the world now on the cusp of climate change. And though impractical, this 12-inch high shoe had an otherworldly beauty to it, which the fashion cognoscenti had no trouble recognizing. The likes of Lady Gaga and Daphne Guinness were seen towering over us mere mortals in this creation, which ‘combined a claw-like menace with the beauty of a ballerina’s en pointe.’ And as if a testament to fashion as an agent of change, three pairs of the boot were snapped up at a Christie’s auction by the pop superstar for $295,000 in aid of UNICEF’s relief efforts in Nepal in 2015.

9. Heelless Shoes

The phrase well-heeled is a euphemism to subtly refer to the ultra-wealthy, as historically, being able to afford good shoes was an indicator of wealth. But what happens when you are so wealthy that you’ve decided to do away with heels altogether? As is the case of socialite and heiress Daphne Guinness, who in the earlier part of this decade braved Parisian cobblestones and Upper East Side sidewalks in heelless Alexander McQueen platforms. Although these boots have been inimitably linked to McQueen, designer Antonio Berardi had actually shown them in his 2007 show, with Victoria Beckham slaying in his heelless boots in 2008. 


10. Salvatore Ferragamo’s Rainbow Sandals

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When celebrated shoe designer Salvatore Ferragamo created these suede platforms for Judy Garland in 1938, could he have perhaps foretold that the American actress would later be so well-known for the balled Over the Rainbow? The multi-colored marvel dubbed the ‘Rainbow Sandal’ has become one of the brand’s most iconic designs, and almost 80 years later as of press time is still available for purchase on the brand’s website. Salvatore Ferragamo is credited as the inventor of the modern platform, and his mark on fashion is felt to this day. Maybe as an homage to the appeal of his enduring style, a giant replica was also created in 2011 when the brand announced its IPO in Milan. And more recently, a limited edition sustainable version in wood and organic cotton was also reissued in 2018 called ‘Rainbow Future.’

11. Vivienne Westwood’s Ghillie Platforms

Design provocateur Vivienne Westwood has long been known for her rule-breaking tendencies and penchant for referencing historical British fashion. Some of her most infamous creations are the Ghillie platforms, which were part of her Fall/Winter 1993 Anglomania collection. Inspired by the ribbon styles of the 18th and 19th centuries, but with a towering 12-inch take, she was once known to have said that "shoes must have very high heels and platforms to put women's beauty on a pedestal.” The shoes were so extremely high that they brought Naomi Campbell to her knees on the runway. But what made the moment unforgettable was how the young model laughed it off and continued on her walk, exemplifying the inimitable grace that made her a true blue supermodel. 


Shoes That Have Stood the Test of Time

Be it sublime stiletto that can make you feel like you’re on top of the world, or your trusty pair of flats that lets you indulge your wanderlust with ease, these are the shoes that have remained chic throughout the decades. 

12. Christian Louboutin’s Red Soled Heels

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One could call it fate, when at one time in 1993 Christian Louboutin had been tinkering with one of his prototypes, which he had found a bit boring, and his assistant had been painting her nails red on the side. As the famous story goes, the designer had the brilliant idea to paint the bottom of his shoes cherry red and the rest is history. Now, these iconic crimson-lacquered soles have become synonymous to luxury, finding themselves adorning the feet and in the closets of the world’s most stylish women.

13. Coco Chanel’s Two-Tone Slingbacks

There are a lot of things we owe Coco Chanel for—the LBD, the use of jersey in clothing, and in terms of footwear, the Two-Tone slingback she created in 1957. Mademoiselle Coco deigned it to be the “the final touch of elegance,” with the nude color elongating the leg and the black toe cap visually abbreviating the foot. The flattering design and elegant hues had the press fawning over it, dubbing it the “New Cinderella Slipper.” It was naturally a hit among the style-setters of the day, with Catherine Deneuve, Romy Schneider, Brigitte Bardot, and Jane Fonda frequently seen strutting in them. Today, these duotone wonders have become synonymous with the House of Chanel, and various iterations have also emerged from ballet flats to boots. But it is perhaps the slingback that is most iconic, and versatile enough to take you from day to night, just as Coco had first intended.


14. Audrey Hepburn’s Penny Loafers

We loved her in ballgowns, but she was equally charming in all her gamine glory. Silver screen darling Audrey Hepburn’s taste for comfortable footwear is something we all can relate to, with her favorite penny loafers still just as youthful and stylish today. She had danced in them alongside Fred Astaire in Funny Face and likewise gravitated towards them for everyday wear. Their insouciant appeal makes them perfect for anything from button-down shirts and skirts, to jeans and cropped trousers. 

15. Kate Middleton’s LK Bennett Nude Court Shoes

If anyone could attest to the benefits of having a trusty pair of neutral heels on rotation, it is the Duchess of Cambridge herself, Kate Middleton. The elegant royal, whom we can assume has a social calendar packed to the brim, is often spotted in a pair of LK Bennett nude pumps and has worn them with everything from smart coats to charming day dresses. Though she’s donned many of the brand’s designs, she seems to favor the classic ‘Sledge’ design with a graceful rounded shape, and the ‘Fern’ which has an elegant pointy toe.

16. Brigitte Bardot’s Repetto Cendrillon Ballerinas

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If you can’t live a summer’s day without your trusty ballet flats, you can probably thank Brigitte Bardot for that. Back in 1956, she had asked Rose Repetto for an everyday pair with the look and feel of a ballet shoe, thus birthing the Cendrillon. And while ballet-inspired apparel had been trickling into fashion for a while, it was the French ingenue’s turn in them in the film Et Dieu créa la femme, that perhaps started this chic trend.  And to further speak of this ballet flat’s sartorial influence, Repetto’s Cendrillon was added to the MoMA’s permanent collection in 2018.


17. Twiggy’s Brogues

With her blond pixie cut and waif-like figure (hence the moniker), Twiggy is arguably the face that defined the ‘Swinging Sixties.’ The British supermodel had been known for marching to the beat of her own drum and the same applied to her taste in shoes. She had been drawn to brogues as a fan of Fred Astaire, but couldn’t find any nice ones made for women. So, she headed off to the Prince of Wales’ shoemaker on Savile Row, and ordered one in brown and white leather. She was then seen and photographed wearing them with such aplomb that she effectively started a footwear revolution.

18. Audrey Hepburn’s Kitten Heels


Kitten heels were introduced in the late 1950s as an appropriate shoe for young girls who weren’t yet used to walking in really high stilettos. However, by the late 1960s, women of all ages had become drawn to their elegance and versatility, including the inimitable Audrey Hepburn. The style icon had been seen in these delicate stunners in her films How to Steal a Million and Breakfast at Tiffany’s, further cementing the shoe’s enduring appeal.

19. Gucci’s Loafers

Designed by Aldo Gucci, the son of founder Guccio Gucci, the brand’s classic loafers with the distinctive metal horse bit first emerged in 1953. Recognizing the appeal of the equestrienne lifestyle among the English aristocracy, the luxury brand had long tried to incorporate these elements into its designs. The classic shoe with its subtle nod to the genteel life became an instant hit, seen on the likes of Jane Birkin, Brigitte Bardot, and other jetsetters. To this day, it’s the favored off-duty shoe of models, celebrities, and influencers alike. 


20. Roger Vivier’s Stilettos

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The delicate genius of Monsieur #RogerVivier embodied here in this floral stiletto from 1959 #tbt #throwbackthursday

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Trained as a sculptor, it is no surprise that the man we can credit for refining the elegant form of the stiletto heel was French shoe designer Roger Vivier. Though heels had been worn for millennia, Vivier’s stilettos had a dangerous elegance to them, achieved by the introduction of a thin rod of steel at the heel in 1954. His opulent creations had been spotted on many of Hollywood’s belles and on royalty. Dubbed as the “Faberge of footwear,” Vivier’s stilettos still remain as one of fashion’s most covetable shoes.

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