The 50 Most Iconic Looks of All Time
Four cities per season. Hundreds of shows per city. Double-digit looks per show. It all amounts to thousands of new runway looks every year. And hundreds more appear on the red carpet and in the streets, where they’re photographed and then broadcast across the world. On social media, millions post their daily dressing rituals, which are then liked and commented on by millions more. We are bombarded with fashion in an endless scroll of outfits. How, then, does a look stand out? What makes it imprint into our collective consciousness and, sometimes, even change the way we dress?
For our annual Icons issue, we sought to not only figure that out but also anoint the most iconic looks throughout history. We started with the nipped-waist jacket and full skirt from Christian Dior’s debut collection in 1947, a revelatory silhouette that ushered in a return to femininity after the ravages of World War II. When she saw it for the first time, legendary Harper’s Bazaar editor in chief Carmel Snow declared it the New Look. It changed fashion forever.
To determine the fashion moments that deserve a place alongside Dior’s watershed New Look, we assembled a brain trust of industry experts, including fashion historian Valerie Steele; stylist and model Dara; image architect Law Roach; Moda Operandi’s cofounder and chief brand officer and artistic director of home for Tiffany & Co., Lauren Santo Domingo; Ssense director of content Steff Yotka; and Lewis’s founder and editor, Jeremy Lewis. Washington Post fashion writer Rachel Tashjian, Interview Magazine’s editor in chief Mel Ottenberg, Nordstrom’s VP, fashion director Rickie De Sole, and writer Liana Satenstein also weighed in, along with a few of our own editors. We debated the merits of hundreds of looks. For each one, we asked, did it become a part of the culture? Are we still thinking about it? Did it shift the way we got dressed? Then we narrowed the results to a definitive 50. Here are our picks, in no particular order.
Christian Dior’s New Look, 1947
“Post–World War II, Monsieur Dior’s introduction of the Bar suit ushered in a distinctly feminine silhouette that empowered women to embrace their sensuality and style. It was and always will be about a return to glamour.” —Lauren Santo Domingo, cofounder and chief brand officer of Moda Operandi and artistic director of home for Tiffany & Co.
Elizabeth Hurley’s Gianni Versace safety-pin dress, 1994
“When Elizabeth Hurley wore Versace’s safety-pin dress, the look immediately became iconic: punk, transgressive, powerful.” —Valerie Steele, director and chief curator of the Museum at the Fashion Institute of Technology
The finale dress from Lee Alexander McQueen’s Joan collection, 1998
“In his extraordinary fashion show devoted to Joan of Arc, the last model emerged wearing a red hooded catsuit within a ring of fire. McQueen has done so many extraordinary looks, but this one was especially powerful, perhaps because it seemed to evoke the designer’s personal story of genius and martyrdom.” —Valerie Steele
Jennifer Lopez in Donatella Versace, 2000
“When Jennifer Lopez wore the dress to the Grammy Awards, millions of people saw it and it entered the Fashion Hall of Infamy, as had the safety-pin dress years before. It was also the inspiration for the launch of Google Images.” —Valerie Steele
Princess Diana’s revenge dress by Christina Stambolian, 1994
“This dress was one of Diana’s most iconic looks and her first hot one, which signaled a newfound independence and confidence post-Charles. It would go on to inspire countless women to embrace their sensuality and boldness with style and vigor.” —Nicole Fritton, executive fashion director of Harper's Bazaar
Grace Jones wearing Issey Miyake at the 1983 Grammys
“This is one of the most perfect examples of how Grace will forever be the ultimate muse and the reason why she is on everyone’s mood board.” —Law Roach, image architect
Michelle Obama in J.Crew, 2012
“First ladies have always used strategic fashion to communicate, but Michelle Obama’s messages came by way of an approachable, non-manufactured style that was wholly her own. When she wore J.Crew during her husband’s presidency, not only did the brand’s sales spike but she signaled to America that she was still a regular working woman and mom, albeit one with inherent style that millions wanted to emulate.” —Brooke Bobb, fashion news director of Harper's Bazaar
Jane Birkin's Jeans and Tee, 1974
“Jane Birkin will always be the blueprint for her perfect white-T-shirt-and-blue-jeans uniform. Her signature basket bag adds to the effortless look, one that represented a new kind of cool girl uniform still relevant today.”—Jaclyn Alexandra Cohen, senior fashion and accessories editor of Harper's Bazaar
Britney Spears’s “Dump Him” T-shirt, 2002
“The right look worn at the right time can say so much, and like its predecessor, Princess Diana’s revenge dress, Britney’s graphic T-shirt and ’70s-revival coat worn after her breakup with Justin Timberlake captures a moment succinctly. Since she wore it, it has cemented its place in the pop-cultural landscape as one of the most influential looks of the era.” —Dara, stylist and model
Gwenyth Paltrow in Tom Ford for Gucci, 1996
“First shown in his Fall 1996 collection, this rich, perfectly cut suit was famously worn by Gwyneth Paltrow to the 1996 MTV Video Music Awards. Alessandro Michele showed a re-edition of it in his 2021 Aria collection, which was worn by Gwyneth that fall—a testament to Ford’s penchant for crafting some of the most iconic suits of all time.” —Nicole Fritton
Bianca Jagger’s wedding suit By Yves Saint Laurent, 1971
“Her wedding dress was iconic because it was a twist on tradition.” —Law Roach, image architect
Angela Davis, 1969
“The Afro itself is one of the most iconic hairstyles of the 20th century. It is synonymous with the Black Power and Black Is Beautiful movements, i.e. Black Excellence. Who better to show it on than Angela Davis?” —Jeremy Lewis, editor and founder of the newsletter Lewis’s
Peggy Moffit in Rudi Gernreich’s Monokini, 1964
“Sixties icon and future incarnate Peggy Moffitt wears the 20th century’s most radical garment: the monokini by Rudi Gernreich. First featured in Women’s Wear Daily in 1964, the design announced the sexual revolution and was an amuse-bouche to second-wave feminism. As Moffitt said in 2012, ‘What was going on was a sort of feeling about sexuality, bosoms, and all that dirtiness. I think Gernreich broke that down. Women have breasts. Get over it.’” —Jeremy Lewis
Aaliyah in Tommy Hilfiger, 1997
“Aaliyah helped propel Tommy to its canonic place within hip-hop fashion history, and the silhouette and styling of this look, trademarks of hers, continue to influence fashion today.” —Leah Chernikoff, executive editor of Harper's Bazaar
Kate Moss at Glastonbury, 2005
“It was the look that single-handedly defined and continues to set the standard for festival style to this day, and it also made us all want Hunter wellies.” —Leah Chernikoff
Sade, 1980
“The hoops. The denim on denim. No one did, or does, effortlessly cool better than Sade Adu, period. She’s a natural beauty who understood early on the power of dressing without a formula.” —Nicole Fritton
Grace Kelly’s wedding dress, 1956
“Created by costume designer Helen Rose, this was the gown that launched a thousand wedding dresses. It’s the blueprint for the classic bridal look, and bridal looks in general, and it still looks modern almost 70 years later.” —Lynette Nylander, executive digital director of Harper's Bazaar
Naomi Campbell finishing community service in Dolce & Gabbana, 2007
“Do I really need to say why this is iconic?” —Law Roach
Maison Martin Margiela’s Spring 1993 collection
“This look encapsulates everything iconic about Margiela’s visionary designs: the Tabi boot, the deconstructed minimalism, and a rough-edged, unrefined beauty that was singularly his.” —Brooke Bobb
Cher in Bob Mackie at the Met Gala, 1974
“Together, Cher and designer Bob Mackie turned red-carpet dressing into a kind of performance art. Her transparent feathered look here paved the way for naked dresses to come and gave new meaning to the art of fashion with a capital F.” —Lynette Nylander
Diane Keaton at the 48th Academy Awards, 1976
“Two years before winning Best Actress at the Oscars for her role in Annie Hall, Diane Keaton launched a phenomenon of women-owning-traditional-menswear-inspired silhouettes, and it just represents American sportswear at its best in this look at the 48th Academy Awards. In the movie the following year, she went so far as to wear a mix of Ralph Lauren and her own wardrobe, creating more unforgettable looks to this day.” —Jaclyn Alexandra Cohen
Björk’s Marjan Pejoski swan dress, 2001
“It has its own Wikipedia page. She laid an egg. It’s a meme. A Halloween costume. A worst-dressed hall-of-fame entry and a best-dressed hall-of-fame entry.” —Steff Yotka, director of content, Ssense
Carolyn Bessette Kennedy in Yohji Yamamoto, 1999
“Carolyn Bessette Kennedy bridged the conceptual gap between Calvin Klein and Yohji Yamamoto. Her pared-down, sophisticated aesthetic defined ’90s minimalism and has inspired collections by Phoebe Philo, the Row, and Tory Burch—arguably three of the most influential designers and brands of our day.” —Jeremy Lewis
Wallis Simpson’s Schiaparelli lobster dress, 1937
“It’s the dress that not only added fuel to a royal scandal but also cemented Elsa Schiaparelli’s status as fashion’s surrealist-in-chief. Its existence helped welcome naughty comedy into highbrow fashion. There’s a reason it’s endlessly referenced.” —Steff Yotka
Betty Catroux in Yves Saint Laurent, 1969
“This is the jacket that started the Saharienne craze. Saint Laurent’s safari look gave women a new way to experiment with a chic utilitarian style.” —Nicole Fritton
Phoebe Philo at her Fall 2011 show for Céline
“The designer’s signature uniform sparked an obsession among stylish women who wanted to be like Phoebe in her Adidas Stan Smith sneakers. It was chic but a little messy, easy but also sharp, cool but never trying to be.” —Nicole Fritton
Rihanna’s Adam Selman crystal dress, 2014
“There’s no topping Rihanna in this transparent Adam Selman crystal number. Not only did it single-handedly create the naked-dress trend but it did something incredible, something few dresses dare to do: make their wearer the star. Here, Rihanna became a true icon.” —Steff Yotka
Alexander McQueen’s “Bumster” pants, 1993
“Lee McQueen blew our collective minds with so many of his radical designs and shows, but the notorious ‘bumster’ pants left a particularly cheeky impression on us all. They were the inception of low-rise pants and whale tails that proliferated through pop culture in the ’90s and early 2000s. He was one of the fashion world’s greatest provocateurs—a true disruptor who was never afraid to crack a joke too.” —Brooke Bobb
Tina Chow in Fortuny, 1987
“Model and jewelry designer Tina Chow had a collection of vintage silk Fortuny dresses, but this one in particular endures as one of the most memorable looks of the decade. It stands out as an early example of a fashion icon drawing upon historic garments to create a completely individual sense of style.” —Dara
Betty Davis's album cover for They Say I'm Different, 1974
“Betty Davis is one of the world’s most underrated style icons. She was quintessential ’70s rock ’n’ roll: silver go-go platform boots, denim hot pants, fishnet pantyhose, and padded shoulder onesies, as evident on the cover of They Say I’m Different, which I think is representative of her singular style. It’s costume, it’s highly creative, and coupled with those cerulean-blue maribou feather ankle boots, it’s perfection!” —Lynette Nylander
Zendaya in archival Mugler, 2024
“The vintage Mugler ‘Gynoid’ Suit, I’m sure, is one of the greatest fashion looks ever made. Debuting in 1995 at Thierry Mugler’s Cirque d’Hiver 20th-anniversary show—it’s always been part of fashion folklore. Never, ever did I think someone would wear it in real life. To be honest, there are so few people who could pull it off. But this is why Zendaya became one of the last daring fashion icons when she wore this to the Dune premiere in February 2024. It’s out of this galaxy, literally.” —Lynette Nylander
Diana Ross dancing at Studio 54, 1979
“This image of Diana Ross dancing in jeans and a ripped tee at Studio 54 is a manifestation of pure freedom and joy. She put aside her glamorous wardrobe in favor of something arguably more chic. It’s the epitome of effortlessly cool style.” —Nicole Fritton
Chanel tweed miniskirt suit, Spring 1994
“Karl Lagerfeld injected a youthful energy and playful attitude to a storied heritage house during his time at Chanel, and the hot, pastel miniskirt suits were indicative of that period. They represented a kind of unabashed glamour that is still unmatched in fashion today.” —Brooke Bobb
Missy Elliott’s “She’s a Bitch” music video, 1999
“I love this look because it’s a mashup of inspiration from iconic movie protagonists, with strong undertones of a dystopian character.” —June Ambrose, creative director and designer
Sharon Stone’s Gap shirt at the Oscars, 1996
“Sharon Stone changed the game in terms of red-carpet style. To wear such an accessible, casual piece from one of the most popular mainstream retail brands in the world is already such a statement. To style it with several designer separates (a Valentino skirt and Armani tuxedo dress worn as a jacket) made even more of a splash. This look showed the world that being fashionable doesn’t mean spending money. The look is relatable, unpretentious, and effortlessly chic, and it’s been referenced countless times since—from Zendaya at the 2022 Oscars to Anne Hathaway’s White Gap dress designed by Zac Posen in 2024.” —Olivia Alchek, senior designer of Harper's Bazaar
Chloé by Phoebe Philo, Spring 2004
“When designer Phoebe Philo took the helm at Chloé, she did not hold back. She created collections that exuded the best of ’70s-era French bohemian style. The banana-print shirt, braided leather belt, and white-hot pants stole the Spring 2004 show. This look was a culmination of everything Philo did at the house, creating hot, playful, and joyful characters.” —Jaclyn Alexandra Cohen
Lee Radziwill and Jackie O in Capri, 1970
“What is chicer than Lee Radziwill and Jackie Onassis shopping in Capri? The sisters solidified the elegance of quiet luxury before quiet luxury was even a thing.” —Jaclyn Alexandra Cohen
Marc Jacobs for Perry Ellis, Spring 1993
“This collection completely shifted the way that people looked at fashion on the runway. It also appalled many editors, retailers, and fashion critics. Jacobs was a pioneer who inspired us to embrace contradictions in the ways we dress. His collection, which ultimately got him fired from Perry Ellis, was ahead of its time in terms of embracing a messy, chaotic sense of style.” —Brooke Bobb
Busta Rhymes’s “Put Your Hands Where My Eyes Could See” music video, 1997
“Inspired by Coming to America, this was our take on urban royalty. It captured the regality of Busta’s character.” —June Ambrose
Christy Turlington, Naomi Campbell, and Linda Evangelista in Anna Sui’s Spring 1994 show
“This was a definitive moment that spoke to a mood of balanced, angelic rebellion. The coordinating babydoll dresses, feather headpieces and boas, ruffle socks, and cake handbags on this beloved super trio stole the show.” —Jaclyn Alexandra Cohen
Lil’ Kim at the MTV Video Music Awards, 1999
“It was the purple pasty seen round the world. When Lil’ Kim showed up to the 1999 MTV Video Music Awards in a one-sleeve purple jumpsuit with only a small sequined pasty covering her left nipple and a matching purple wig, she set the standard for the daring, risqué looks the award show would become known for. Misa Hylton, the legendary stylist and designer responsible for creating the look, was the architect of so much of that era-defining ’90s hip-hop style. This look was so epic, and at the time so bewildering, that Diana Ross, who presented alongside Lil’ Kim that night, couldn't resist jiggling the pasty-covered boob.” —Leah Chernikoff
Stevie Nicks, 1975
“Embellished shawls, flowy kimonos, layered jewelry, eccentric headwear—Stevie Nicks’s outfitting and general vibe is iconic. She is the ultimate bohemian, witchy rock muse.” —Perri Tomkiewicz, digital design director
Hood by Air, Spring 2015
“No designer this century has more forcefully shaken our assumptions about beauty, novelty, and even the purpose of fashion itself than Hood by Air’s Shayne Oliver. In the middle of his Spring 2015 show, he sent out eight models wearing the exact same outfit: an embossed leather jacket, no shirt, black jeans with HBA logos on the knees and boots. Several of the models even looked remarkably similar. Very few designers are willing to toss their hands up at the conceit of a runway show, which press on stubbornly even though everything else about the world has changed. It was shade, a joke, a thesis, and a snarl at our shrinking attention spans all at once.” —Rachel Tashjian, fashion writer, The Washington Post
Chloë Sevigny at the 1996 premiere of Trees Lounge in New York
“This photo was taken two years after the 1994 New Yorker profile that declared Chloë Sevigny the coolest girl in the world. And while there are thousands of photos of Sevigny that could be presented to corroborate that claim, this one feels particularly incontestable. Sevigny is wearing a beaded dress, which surely feels vintage, with a floral corsage pinned to the asymmetrical strap, bold tiger-print stockings, and peep-toe sandals. She has long cemented her status as not just an It girl but the It girl because of looks like this, with styling that feels entirely personal before personal style became a buzzword. She wore things—and still does—with a cool composure and almost indifference, making her style impossible to imitate. Fashion girls will stumble upon this photo for years to come and style their cocktail dresses with tiger tights, but Sevigny will always be the one who did it first.” —Tara Gonzalez, senior fashion editor
Madonna in Gucci at the MTV VMAs, 1995
“Fall 1995 was the season Tom Ford really arrived at Gucci, and no one embodied that hot super glam new direction more than Madonna at the VMAs that year. The jewel-tone satin shirt unbuttoned and low-slung hip huggers made up the defining, key look of that collection, and it was onstage for the world to see.” —Rickie De Sole, VP, fashion director of Nordstrom
Beyonce’s Roberto Cavalli dress for “Hold Up” in Lemonade, 2016
“Beyoncé’s Lemonade felt like a turning point in her career. The release of the album and accompanying film project transformed her from pop megastar into a bona-fide artist. This dress, from Roberto Cavalli by then creative director Peter Dundas felt like a pun (due to its hue) and a statement all in one. The way the ruffles free-flowed while she hit cars in a joyous rage was the perfect accompaniment to the song and has now become one of her most memorable looks.” —Lynette Nylander
Stella McCartney and Liv Tyler at the Met Gala, 1999
“Love these two delicious beauties—Stella McCartney and Liv Tyler—at Met Gala ‘Rock Style’ in 1999. McCartney, who was heading up Chloé at the time, is the daughter of Paul McCartney of the Beatles, and Liv Tyler is Aerosmith’s Steven Tyler’s gorgeous spawn. The two attended the Met Gala in McCartney’s fabulously naughty pieces (McCartney wears EPIC bedazzled peel-them-off pants from Spring 2000). But the real moment that Stella got her freak on? The Hanes off-the-shoulder T-shirts bedazzled with ‘Rock Royalty’ from the store Filth Mart. Stella, creative director at Chloé from 1997 to 2001, famously made clothes inspired by how her girlfriends would wear, so the looks felt so self-styled and natural. There was no ‘full-look’ brain in sight—this Met gala look was the best example of that ethos!” —Liana Satenstein, writer
Janet Jackson performing “Rhythm Nation,” 1989
“When the video for ‘Rhythm Nation’ came out in 1989, the era of Reagan to Bush and the Central Park Five trial, it completely changed the game. It was the height of MTV, and Jackson understood the value in using music and imagery simultaneously to engage viewers in important sociopolitical messaging. ‘Rhythm Nation’ was a call for unity and resistance, and Jackson’s black military-style uniform became a sartorial symbol of power that is as strong today (maybe even stronger) than it was then.” —Brooke Bobb
Sarah Jessica Parker in Alexander McQueen at the Met Gala, 2006
“For the 2006 Met Gala, Sarah Jessica Parker attended with Alexander McQueen in coordinating red tartan sash ensembles for the ‘Anglomania’ theme. Parker famously, at the time, said she was extremely nervous the whole night because of how much she admired him; she even went as far as to say she ‘was in love with him.’ The standout look cemented Parker as a real fashion girl, not just an actress who played one on TV.”—Tara Gonzalez
Madonna, Blond Ambition tour, 1990
“Madonna’s Blonde Ambition tour look with the black suit and pink cone bra is one of the best-designed looks of our lifetime. It’s a tour look, but it’s also FASHION, and it’s truly unsurpassable!” —Mel Ottenberg, editor in chief, Interview
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