Apr 22, 2024
A celebrity claps back at a troll: iconic. Beyoncé exhales: iconic. Jennifer Lopez wears that Versace dress again, and she’s regained her fashion icon status. What’s clear is that the very meaning of “icon” has become oversaturated, overused, and detached from its original context—especially when it comes to fashion. If like us, you could do with some much-needed clarity about this coveted title, keep on reading as we set the record straight.
What Is a Fashion Icon?
Romeo once said that “a rose by any other name would smell just as sweet,” and while his love-blindness may have hindered his fashion eye, he makes a good point. Plus, we’re a sucker for a romantic declaration. You see, a fashion icon is less about the title and more about the ingrained sartorial approach and influence a person carries. For instance, though Anna Wintour is widely considered to be the face of the fashion world (read all about the esteemed editor-in-chief in our biography review), with her golden touch influencing designers and editors alike, she is not a fashion icon; she’s an icon within the bubble of fashion. Her uniform of printed midi-dresses, knee-high boots, and Chanel sunglasses, has situated the Condé Nast leader firmly amongst the stylish elite, but she has not yet become a style maverick—that’s right, there’s still time.
To be considered a fashion icon, your style must either create cultural conversation, have trend-worthy appeal, or most commonly, outlive you. If you have all three you become a fashion triple threat, soon to be encapsulated in Pinterest boards and rewarded with retweets for eternities to come.
There’s no fast-track to this prestigious position, but what it boils down to is consistency—the ability to serve a look at a moment’s notice. One red carpet outfit could be your stairway to fashion heaven, and another could be a walk of shame to a not-so-haute hell. So, how do you incorporate all these lessons into your own sartorial decisions? Below, we’ve rounded up the 20 most influential fashion icons who are quite literally bursting at the seams with style.
1 / 20
Princess Diana
As a royal, she stole our hearts and as a fashion icon, she continues to influence our style choices. At the start of her royal tenure, the young princess was largely photographed in ’80s style garments, think lots of frills and bows. However, the trendsetter soon discarded dresses synonymous with traditional aristocratic attire, trading the garish garments for much sexier silhouettes like Versace dresses and Dior accessories.
But what makes Princess Diana’s style so appealing, is how she used fashion as an extension of her personality; each outfit was evocative of the warmth and charisma she possessed. Whether she was dropping her children off at school in collegiate jumpers and cycling shorts or attending to her charitable duties in a casual blazer and loafers, her fashion never faltered. And while it’s her coherent and consistent disposition to dressing that has cemented her as a fashion icon, the Princess was unafraid to go against the grain and sport unexpected looks. Two words: revenge dress. The black plunging Christina Stambolian dress is one of Princess Diana’s most iconic looks, first for its sultry air, and, second, for the implication behind it. The revenge dress was the perfect culmination of circumstance and sartorial mastery, making its public debut on the same evening King Charles admitted to his affair with Camilla Parker-Bowles.
But the true testament to the Princess’s icon status is how her fashion exists beyond her. You only need to open a magazine to see how her aesthetic continues to be on-trend. Plus, thanks to The Crown, her polished blazers and accessories are once again at the forefront of our closets.
2 / 20
Rihanna
The singer, designer, and melting pot of multi-hyphenates is a fashion icon simply because she has put in the work, work, work, work (sorry, it was right there). From her baggy jeans and crop-top outfits, which dominated the noughties, to her confident modern-day aesthetic, Rihanna’s style trajectory is one for the history books. Her affinity for sporting cult designers before they turn mainstream (see Molly Goddard) and spotting trends in advance have cemented her icon status and enabled her to cultivate her own fashion empire: Fenty.
What gives Rihanna her icon edge is that she appreciates the craft and history of fashion. You only need to look at her eclectic array of Met Gala outfits to know this. In 2015, she made headlines by arriving at the annual event in a show stopping ensemble by Chinese couturier Guo Pei, which was not only sought out by the singer, but also took over two years to make.
And, if you’re doubting Miss Fenty’s influence, let’s remind you of how a single image of her sporting a pair of Dolce & Gabbana headphones caused the $9,000 accessory to sell out everywhere. Now, that’s what we call a style icon.
3 / 20
Zendaya
As the youngest on our list, Zendaya (26) shows that you don’t need age on your side to become a fashion icon—you just need to make decisive style choices. Hailing from the halls of Disney Studios, the young star’s initial fashion approach was what you’d expect, a mismatch of colorful layers and sneakers. However, after meeting stylist Law Roach, everything changed. The young star exchanged her pragmatic “girl next door” image for a more purposeful approach, donning designers that would garner attention from best-dressed lists and would give her the freedom to carve a different fashion path—one where she looks equally as elegant in a men’s Berluti suit as she does in a silk Vera Wang gown.
What’s more, her fashion touch has even been noticed by esteemed designers. In 2019, Tommy Hilfiger enlisted Zendaya in making a capsule collection for his namesake brand and she was made a Valentino brand ambassador in 2022.
4 / 20
Audrey Hepburn
Audrey Hepburn is synonymous with a multitude of things: breakfast, Tiffany & Co., and most importantly fashion. After meeting Hubert de Givenchy in the early ’50s, she quickly began a love affair with clothes that would last a lifetime; her delicate, slender frame was the perfect medium for showcasing the designer’s haute couture collections. But Hepburn’s arrival at fashion icon avenue is a result of one of those rare moments where the right silhouette and the right star can create a symbiotic relationship that everyone benefits from.
The opening of the 1961 movie Breakfast at Tiffany’s saw Hepburn sporting a seamless black dress, which just so happened to be custom made by Givenchy. The beloved reception of the romantic comedy thrust the designer and Hepburn further into the spotlight, cementing their star power forever. Today, you can’t say the phrase “little black dress” without Hepburn or Givenchy’s names shortly following in the same breath.
If you want to mirror Hepburn’s ethereal charm without going for the obvious choice, why not take inspiration from her summer wardrobe? With style-options ranging from ballerina-style flats to wide-brim straw hats, you can go big with your Old Hollywood interpretations.
5 / 20
Harry Styles
His boy band roots of black skinny jeans and paisley-print shirts aside, Harry Styles is a fashion icon for the new age. Whether he is wearing custom Gucci or breaking the boundaries of masculinity in a bespoke Harris Reed dress, the singer isn’t shy of serving a look or two. While there is no denying his star power (he’s spearheading the pearl necklace revival), we’re firm believers in giving credit where credit is due—calling Harry Lambert. As Styles Stylist (say that four times after a few cocktails), Lambert is very much the mastermind behind the singer’s Gucci-clad looks. His ability to mix masculine and feminine silhouettes in a cohesive manner has made Styles’ star quite literally brighter. However, what separates Styles from being typically trendy or just another name on a men’s best-dressed list is that his garments constantly ignite cultural conversation.
So, take a leaf out of Style’s book, or in this case a piece out of his wardrobe, and bask in the chance to be the word on everyone’s lips. We recommended hitting the ground running in a pair of Gucci Slingback Heels.
6 / 20
Solange Knowles
While maybe not the obvious choice, Solange Knowles is a fashion icon to the contemporary mind. Her 2017 album A Seat at the Table spotlighted her artistic talents and brought forward her stylish sensibilities. It doesn’t matter if the singer is wearing a Thom Browne puff jacket to the Met Gala or Brother Vellies boots on city sidewalks, Knowles’ outfits are the exhaled breath to her artistic vision, crafted with the aim of capturing a certain mood or feeling.
Whereas many men can wear the same gray suit fifty times and still be considered style innovators, the same cannot be said for women, who are constantly having to transform themselves in order to be considered relevant. But Knowles takes this transformative aspect to the next level, expanding the breadth of her vision with each new walk of life; it’s this chameleon approach that allows her to reside with the other fashion icons on this list.
7 / 20
Billy Porter
It’s fitting that Billy Porter is one of the stars of the American drama Pose as he most certainly knows how to stand his own on the red carpet. Much like Styles, Porter takes the notions of gender and bends them how he sees fit, which in our opinion, he does fabulously. From long train Christian Siriano gowns to stand-out Harris Reed hats, Porter uses garments as a way to create space both figuratively and literally. There’s no subtly to his approach—he is not defying the normative by simply wearing an earring. Instead, he is challenging style conventions head-on by staying true to himself. And isn’t that what a fashion icon is all about? Marching to the beat of your own drum.
8 / 20
Jackie Kennedy
Long before Jackie Kennedy took over the reins as First Lady, she was already putting in the work to become a fashion icon. With her New England air, this style maverick was accustomed to collegiate fashion and classic turtlenecks. However, as her star began to rise, her clothes changed, too. The domestic garments of yesteryears were traded in for fine fitting Chanel suits, her signature pillbox hat, and Gucci’s classic Jackie bag, named after the First Lady when she used the luxury purse to shield her face from the paparazzi.
Though it’s her polished presidential look that has been immortalized in our wardrobes, her ’70s attire is what captivates us. Soon after marrying ship tycoon Aristotle Onasis, the public began to see a free-flowing approach to fashion—a reflection of the times and her newfound happiness. The surefire sign of this nonchalant disposition is found in the oversized, round sunglasses that she regularly sported throughout the era.
9 / 20
Chloë Sevigny
Chloë Sevigny’s style seems to live outside the reality of what’s trending or what’s cool, while somehow still feeling relevant. She says jump, we ask “how high?” She goes left, we follow. She wears a pair of sandals and passersby stop to ask of their origins. Whether she’s in Paris wearing Miu Miu or taking her son out for a walk in Simone Rocha, there is always an easy-breezy element to the actress’s attire.
But interestingly, Sevigny’s fashion icon status wasn’t purposely pursued with the aim of getting public attention; she is an accidental icon. In a way, that’s what makes her somewhat ordinary style endearing. She is not dressing to send a message or please the fashion powers above—the Dr. Martens she wears day-to-day are completely her own. And we look forward to seeing how her style involve as she enters the next phases of her life.
10 / 20
ASAP Rocky
As a fashion icon, ASAP Rocky resides in one of the rarest places, between the intricate designs of haute couture and the casual silhouettes of streetwear. No matter if he is at a Dior Homme fashion show or sharing his Supreme fits with his 15.2m Instagram followers, the hip-hop darling seems to always retain his enigmatic energy and stylish sensibility. Not to mention, he has the face of a model: an attribute that hasn’t gone unnoticed by Rihanna who has made him an ambassador of Fenty Skin.
But perhaps what consolidates his fashion icon status is his unfaltering confidence. The New York City native knows he is a fashion icon and he is not going to apologize for it. In fact, in his 2014 track “multiply” the rapper admits how he’s no longer a fan of the streetwear brand Hood by Air, claiming that he was the one that helped pioneer it. As a result, multiple fans went to eBay to sell their HBA apparel. That’s what we call influence.
11 / 20
David Bowie
There’s an undeniable theatrical element to dressing; it’s the chance to express yourself, don a different personality, and escape the realities of everyday life. As one of our resident fashion icons, David Bowie takes this theatrical aspect and runs with it—far. His affinity for manufacturing alter-egos and using them as a medium of creative expression has positioned him as one of the most influential fashion minds of all time. From the bright palette of his Ziggy Stardust and Aladdin Sane days to the louche looks of the Thin White Duke era, Bowie’s outfits are still the topic of the conversation and the driver of trends.
Jean-Paul Gaultier’s Spring/Summer 2013 show not only legitimized the singer’s legacy, but also highlighted how his influence is felt by men and women alike. The pop star-inspired pieces convey a fantastical world where the only limitations are your imagination. So, why not climb aboard the Bowie express? Your first-class ticket can be found in Etro’s paisley print tie.
12 / 20
Cher
Some say that icons are born not made and Cher’s very existence attests to this belief. The singer’s sequin drenched ensembles beckoned a new age for performers as her outfits challenge the societal standard of how a woman should look or act. When she arrived at the 1986 Oscars to present the award for the best supporting actor, her black jewel-encrusted headpiece and feathered hat garnered the attention of the masses; the Bob Mackie original look was commissioned by the star as a way to get back at The Academy after being snubbed.
But while Cher’s sensual silhouettes leave us salivating for more, it’s her bohemian uniform that sets her apart from simply being another red carpet memory. Stemming from the ’70s attire she sported on her show the Sonny & Cher Comedy Hour, the singer has cultivated a relaxed but equally fashionable look that perfectly complements her slender frame and customary jet black hair.
13 / 20
Victoria Beckham
If someone told us that this is Victoria Beckham’s world and we’re simply living in it, we wouldn’t doubt them for a second. Beckham has worn a series of hats, from pop star to footballer’s wife to designer, but these stand-alone acts haven’t led to a curtain call. In fact, the very opposite. With each new venture, this jack of all trades has been working to establish a bigger role of stature and influence, one that can be summed up in two words: fashion icon.
Whether she is wearing a black mini dress and platform sandals during the peak of her Posh-persona, or she’s keeping it casual in a merino wool sweater, Beckham knows how to put together an outfit that wows without being too far off from her personality. But what keeps the designer firmly placed on her fashion icon pedestal is her ability to move with the times, instead of waiting for time to move her long. While she just turned 48 this past April, Beckham’s fashion stride is not slowing down—an unsurprising fact considering her namesake label has become synonymous with the type of modern woman who works hard and plays hard and looks fabulous while doing it.
14 / 20
Madonna
Madonna has been making waves in both the music and fashion world since her debut album. Lauded for her continual reinvention and influence, the singer’s style choices can still be felt on a street style and catwalk level today. But, aside from making ’80s layered skirts and leggings popular (*shudders*), Madonna’s style redefines the feminine stereotype of women having to embody delicate forms in order to be seen as attractive.
One look which perfectly showcases this is the singer’s tomboy aesthetic in the Papa Don’t Preach music video. The combination of her bleach-blonde pixie and grunge style evokes a feeling of casual beauty, with a hint of “don’t try me” attitude.
15 / 20
Timothée Chalamet
Timothée Chalamet, much like Zendaya, has quickly risen through the ranks to stake his claim on the coveted title. Maybe it’s his boyish charm, his prince-like features, or the fact he knows how to bend the fashion normative to his advantage.Whatever the reason, it seems the public (ourselves included) can’t get enough of his fashion-forward fits. From a bespoke Louis Vuitton “harness” to a more streamlined Haider Ackermann shirt-and-trouser combination, it’s apparent the young actor is proving to be a muse for the modern man. And if his acting career is anything to go off of (he has received both Oscar and Golden Globe nominations), we have no doubt that his sartorial standard is only going to rise.
16 / 20
Grace Jones
Give Grace Jones a room and she will make it her own. The model, pop-star, and “it” girl of the nightlife scene, has very much carved out her own path as a fashion icon. Though somewhat outlandish (think over the top Philip Tracey headwear), this multi-hyphenate is the epitome of sex appeal and androgynous style. Whether she’s high-flying to the rhythm at the once celebrity hot spot of Studio 54, or kicking it with royalty at Queen Elizabeth II’s diamond jubilee, no matter the occasion this superstar knows how to serve a look.
The premise of Jones’ appeal does not lie in extravagant or loud designs, it comes in the common thread of her not swaying to meet societal standards.
17 / 20
Twiggy
No one defined ’60s fashion quite like Twiggy. The model’s long legs and doll-like features quickly made her the face of Mary Quant mini-skirts and mod style, which dominated this particular era. However, Twiggy wasn’t just a magazine maven and her influence didn’t end as the ’70s began. The model’s understanding of clothing and knowledge of utilizing silhouettes to embolden her features enabled her to take her career beyond modeling into the realms of singing, acting, and reality TV (she appeared as a judge on seasons six through nine of America’s Next Top Model). Ultimately, Twiggy’s career trajectory is a testament to the shifting power of great style.
18 / 20
Michelle Obama
Much like Jackie Kennedy’s fashion lifecycle, it’s Michelle Obama’s post-presidential style that has truly established her as a fashion icon. Though her tenure as First Lady caused many a designer dress to sell out, it was when Obama was no longer confined to the restrictions of the White House that she was truly able to find her footing in fashion—and when we say footing we mean the sequined Balenciaga kind. On her stadium-wide book tour, Obama sported a series of looks, but one which garnered the most attention was her Balenciaga silk dress and sequined boots.
Though there’s a clear style distinction between her time as First Lady and now, one thing that remains true is her desire to spotlight up-and-coming designers. At Joe Biden’s Inauguration, the former First Lady was seen sporting a full burgundy look by L.A.-based designer Sergio Hudson, who is known for his sexy silhouettes and use of silk. Today, Michelle Obama’s style remains the topic of conversation due to her grace and fashion-forward thinking.
19 / 20
André Leon Talley
When it comes to being a fashion icon André Leon Talley is unlike anyone else. Not only has he made oversized puffer jackets and free-flowing kaftans his own, but his fashion knowledge and experience as Anna Wintour’s right-hand man also means he has become a brand in his own right. The release of his 2020 memoir, The Chiffon Trenches, once again brought him to the forefront of the fashion industry, as he was unafraid to ruffle a few feathers (faux, of course). And further proving his influence, the fashion journalist started the new year as the face of UGG’s latest campaign.
20 / 20
Carolyn Bessette-Kennedy
Saving the best for last, it wouldn't be a fashion icon list without Carolyn Bessette-Kennedy. The wife of John F. Kennedy Jr. and former Calvin Klein publicist, Carolyn Bessette-Kennedy was considered American royalty for her girl-next-door looks and effortless personal. Defined by its minimalist charm (think classic white tees and dark wash jeans), Bessette-Kennedy was a firm believer in investment dressing and not buying into trends—for her wedding, she disregarded the puffy silhouettes that were en vogue in the '90s and opted for a slip silk dress.
