Music’s 40 Greatest Style Icons, Ranked

Imagine if The Beatles never wore those collarless suits, or if Madonna never wore a tattered wedding dress on MTV. What if David Bowie had never thought to transform into Ziggy Stardust, or Cher had never worn that glittery body stocking under a leather jacket on a Navy ship? No meat dress for Gaga, no ruffled shirt for Prince, no cape for James Brown, no trash bag jumpsuit for Missy Elliott.

Fashion changes the perception of artists, particularly those who routinely get up in front of thousands to perform. If musicians so choose, style choices can reflect and support their artistic choices. Many of the 40 icons of personal style on this list have used clothes in a conscious, specific way. As the list progresses towards the top, that becomes more and more apparent. — Jillian Mapes

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40. Solange

Solange’s style isn’t the most outrageous of the rest of the looks on this list, but the younger Knowles sibling’s ability to mix bold patterns, utilize African prints, and color-block has helped to cement trends and highlight up-and-coming designers along the way. — JM

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39. Sly Stone

Seventies funk had no shortage of incredible costumes, from James Brown cutting his jumpsuits low to Bootsy Collins’ star-studded leather. But there was something about the way Sly Stone put together a look, oftentimes mixing Parliament’s theatricality with the slightly disheveled psychedelia of Jimi Hendrix. Patchwork denim, wide-brimmed hats, masculine necklaces, and a vast vest collection made Sly stand out, even amongst his equally fashionable Family Stone bandmates. — JM

duranduran38. Duran Duran

Of all the style icons of the ‘80s, Duran Duran are perhaps most notable for not falling victim to too many of the pitfalls of that decade’s style, other than big, big hair. Besides that, they’re probably best known for their rock group styling, opting mostly for sharp suits and glamour instead of the overly ruffled, oversized suits of other ‘80s acts. And, believe it or not, in 2011 they were actually honored by the mayor of Milan as style icons. So, uh, that’s proof enough, right?  — Shane Barnes

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37. Janelle Monáe

Janelle Monáe’s default tuxedo look is inspired by menswear of bygone eras as much as it is the concept of a uniform, as an ode to her working-class parents. Saddle shoes, a classic pleated bib tuxedo shirt, and snugly tailored pants find a balance with Monáe’s signature bouffant and a bright lipstick. “I feel like I have a responsibility to my community and other young girls to help redefine what it looks like to be a woman,” she said of her style. “I don’t believe in men’s wear or women’s wear, I just like what I like.” — JM

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36. The Velvet Underground

The Velvet Underground represent the effortless cool of a rock and roll band who doesn’t give a shit, but they didn’t need to give it a uniform like The Ramones. They paired the basics of the era — turtlenecks, corduroys, and college prof jackets — with Ray-Bans, pointy boots, and looks of indifference. In the fashion sense, VU were the opposite of The Beatles, even if both groups would have bonded over a love of leather jackets at various points in their careers. It was not about matching on purpose, but rather, inadvertently looking like a group because of a shared embrace of all things hip-to-be-square. Nico brought a sense of classic chicness to the group, while standing next to Warhol inherently made them look cooler. — JM

Missy Elliot at Lilith Fair

35. Missy Elliott

Sweatsuits, Adidas, embellished denim, fuzzy fabrics, colored leather, and of course, those “Supa Dupa Fly” trash bag suits: Missy Elliott never intended to look sexy or even terribly cool, but she did elevate hip-hop trends of the late ’90s and early ’00s to crazy heights. Her over-the-top treatments would inevitably turn her looks into something much bigger than their inspiration points. She’d stand out in a sweatsuit instead of looking like one of the guys. She’d wear a Barney-purple leather suit complete with flares and elaborate embroidery to the Grammys. — JM

fashion_jarviscocker 34. Jarvis Cocker
Cool Britannia found an icon in Pulp leader Jarvis Cocker, whom I’m not quite sure I’ve seen out of a suit jacket. Cocker’s style has matured as he has, starting with the t-shirt/jacket combo before evolving into tailored business casual. These days, he makes Elaine Stritch glasses, ties, and tweed look cool without resembling someone’s grandpa. — JM

fashion_boygeorge33. Boy George

Who can forget Boy George’s get-up in Culture Club’s “Do You Really Want to Hurt Me” video? That derby, those weird, braided extensions, that sweater dress. This is a look you will still see, in 2014, in certain parts of Manhattan after 3 a.m. Since the late ‘90s, George has been more prolific on Broadway than on record, and has been dressing kind of like a sad clown — a distinctive look, sure, but it probably won’t be seen on the streets anytime soon. — SB

fashion_rihanna32. Rihanna

Sex. Sex, with moments of trendsetting street style. But, mostly, sex. Rihanna has transformed her look with each album, but only just slightly, and each with its own angle on sexy. And Rihanna owns her look with such unapologetic confidence that it becomes more than that — it becomes this whole image of empowerment that balks at any old white man who wants to say girl looks “slutty.” — SB

fashion_jimihendrix31. Jimi Hendrix

Pretty much the king of the psychedelic silk blouse and bell bottoms — or just a plain old tripped-out jumpsuit — Hendrix’s wardrobe was as signature as his guitar playing. Paired with his headbands and copious jewelry, as well as an overwhelming amount of purple, Hendrix was perhaps the most fashion-influential of all the guys who loved the word “psychedelic.” — SB

fashion_Rollingstones30. The Rolling Stones

The Rolling Stones started out and evolved a bit like the Beatles, debuting in full-on proper suits and quickly devolving into barely-buttoned rockstar looks. Mick Jagger and Keith Richards broke away from the rest as style icons, though. Mick keeps it somewhat classy in tailored pants and flowy, er, blouses, while Keith goes full-on rockstar, letting his hair fall into a nest of banded dreadlocks and sometimes not even bothering to wear shirts under his pirate-inspired overcoats. There’s a reason Keith Richards’ likeness has become inspiration for the archetypal rockstar, and it’s not his alligator skin. — SB

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29. Patti Smith

The cover of Patti Smith’s 1975 album Horses is how everyone thinks of Patti Smith, regardless of whether or not that’s how she’s looked a single day since then. And that’s fine, because it’s a damn good look, her white button-down and leather pants becoming the go-to inspiration for tough-ass musician poets the world over. She’s rocked a variation of the thing ever since, combining menswear with a waifish attitude (and, lately, hats) in a way that only Patti Smith can. Like the hard-ass version of Annie Hall, maybe. — SB

fashion_bjork28. Björk

Icelandic powerhouse/faerie Björk’s style is a consistent “what the fuck?” broken up by random moments of transcendence, à la the Swan Dress. So, as in all things, Björk is an outlier here, her style being beyond summation but still also so signature. From super big hair to futuristic geisha, Björk’s looks have gone as many places as her music. — SB

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27. Johnny Cash

The Man in Black was a badass, but his clothes didn’t necessarily show it. Sure, his color choice accentuated his intensity, but his clothes were always tailored, neat, and classic, with just a touch of edge via leather jacket or later in life, shaggy hair. At a time when his male peers in the country world were wearing Nudie Suits and ten-gallon hats, Cash opted for his own way of expressing his demon-filled masculinity, damnit. — JM

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26. Marc Bolan

Perhaps even more so than Bowie, T. Rex’s Marc Bolan will always be known as the King of Glam,often wearing cat suits, psychedelic jackets, oversized top hats, and way too much cheetah print, his powdered face curtained by big, black curls. Rockstars have basically made Bolan’s look into a guide for how to dress. See: The Darkness, Lenny Kravitz, Slash. — SB

25. Annie Lennox

What’s to say about Annie Lennox, she of the Eurythmics and the prolific solo career, other than “androgyny”? The chopped red locks, the tailored suits, the made-up face —  it’s clear Lennox took cues both from Bowie and Grace Jones. Actually, looking at it, she could be the style baby of those two greats. — SB

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24. Spice Girls

The Spice Girls weren’t always unified in their styles, but they did find some common ground: platforms, bright colors, bare midriffs, short skirts, and a real sense of personality and playfulness in their clothes. Though the worldwide reign of Girl Power ambassadors Baby, Scary, Ginger, Sporty, and Posh lasted just two albums, their looks became internationally synonymous with 1990s fashion trends. — JM

Little Richard

23. Little Richard

Little Richard was the first rock’n’roll star to push the boundaries of flamboyance. Marathon sessions spent standing at the piano necessitated a slight bagginess in his early suits, but Richard Wayne Penniman maintained a glamorous style with a lifelong trifecta of big hair, skinny mustaches, and more and more sparkle over time. He was not above taking off his shirt, rocking fringe, and really committing to bold style choices. — JM

fashion_kurtcobain

22. Kurt Cobain

Kurt Cobain wasn’t an icon who stood out from his scene, but rather, embodied it. Flannel, Converse, stone-wash jeans, greasy hair, and a no-fucks-given attitude has never looked better on anyone than it does on Kurt Cobain, though many have tried. — JM

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21. Buddy Holly

Blame Buddy Holly for plastic black glasses as a life philosophy, for the oxymoronic world of the “cool nerd,” for nice-guy rock stars who think sweaters make acceptable stage wear. — JM

andre 3000

20. André 3000

Afro-funk futurism: that’s what I’ll call André 3000’s most distinctive personal style. Tons of wigs, bug-eyed sunglasses, bell bottoms for days, only the brightest colors, ’70s plaid. Andre’s style has often combined so many influences that it’s become a thing all its own — kind of like the music of Outkast. Nowadays, he’s more prep than anything else — see his failed fashion line Benjamin Bixby — but he’s bringing that better than most people, too. — SB

fashion_GwenStefani

19. Gwen Stefani

The No Doubt singer has gone through a few variations of the same look, most of which have revolved around plaid and bikini tops. When No Doubt broke big in ’90s alt-rock, Stefani played the role of punk tomboy, complete with Dickies and wifebeaters; pink, blue, and platinum locks on a rotating basis; and for some reason, a bindi. As No Doubt entered the new millennium and started infusing dancehall into their sound, Stefani incorporated Jamaica’s colors — red, green, and yellow — into her style. As she mounted a solo career and various fashion endeavors in the pop mainstream, she’s shifted towards frilly, girly looks. — JM

fashion_stevienicks

18. Stevie Nicks

Girls with a thing for witchwear — flowing shawls and dusters, maxi skirts, big hats — would be tragically lost without Stevie. She pulls it off without it looking like she’s wearing a costume, thanks to a 1970s West Coast bohemian ease that permeates her most layered looks in black. — JM

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17. Tina Turner

Tina Turner’s personal style has always revolved around short, tight, and full of movement. But a diva can’t dress in fringe alone. As she’s mounted an ’80s comeback, Turner embraced modern style with the help of fashion designer Bob Mackie. Leather and gravity-defying wigs became her focus — that is, besides her incredible legs. — JM

fashion_elvis

16. Elvis

There are articles of clothing we might not have so closely associated with rock stars had Elvis not cemented the image: swooping hunk of hair, tight pants, leather jackets, and jumpsuits with a touch of sparkle. At first Presley’s clothes were by the book, adhering to trends of the era whole throwing in a little bad boy attitude. But as time went on, Elvis really grew into his Vegas persona, allowing the glamor of show business to meld with his country boy swagger. — JM

fashion_DianaRoss

15. Diana Ross

Easy glamor and big hair (early-era beehive and otherwise), that’s what the Supremes singer is probably best known for — well, that and her ability to be extremely poised while also being an intense hard-ass. The very definition of a diva. — SB

fashion_freddiemercury

14. Freddie Mercury

Freddie Mercury lived in the prime era for rock frontmen, but the Queen singer felt like one of the few who innately understood the theatricality required of the job. His fondness for capes, glittery bodysuits, Adidas, and all things tight and chest-baring made for an odd mix at times. Chalk it up to the showmanship. — JM

courtney-love

13. Courtney Love

The babydoll dress became synonymous with the 1990s and punk girls because of Courtney Love. The disheveled female rocker found one of its greatest icons in her, too. But perhaps the most impressive thing about Love’s style evolution from ripped slip dress to silk charmeuse gown cut on the bias is that she really committed to both looks — the rocker and the old Hollywood starlet — and eventually merged the two into a designer-heavy look of messy glamor. It declared to the world, “I contain multitudes.” — JM

fashion_ladygaga

12. Lady Gaga

Disco-ball leotards, Bowie worship, facial prosthetics, 10-inch Alexander McQueen stilettos, a machismo male alter-ego, an outfit covered in Kermit faces, bright ombre hair before it was a thing, bloody lace, plastic bubbles, bows made out of hair, that meat dress, almost nothing at all. Lady Gaga is ceaseless in her dedication to standing out on every level, from the highest of couture all the way down. — JM

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11. James Brown

James Brown started off with a signature look, but as times shifted away from tailored three-piece suits as a must for male entertainers, so did his stage wear. Eventually, nothing became off limits in Brown’s looks: zippered jumpsuits that showed off his chest hair, bejeweled jackets, colorful printed scarves, ornate capes that brought drama to his “Hardest Working Man in Show Business” routine. — JM

fashion_kanye

10. Kanye West

Even before Kanye ranted about leather jogging pants, and even before he started acting as his wife’s personal stylist, and even before he made the fashion mullet a thing, Kanye was a fashion icon. Not necessarily a good one — he was rocking too-big Polos and way too many so-called luxury brands (YSL, Gucci, etc.). Essentially, he began as Basic Kanye, and even then he was an icon. He’s evolved, designed his own lines, and made fashion almost as much of a priority as music. And, now that he’s got a family to deck out in Givenchy and Balmain, his influence is probably wider than ever. — SB

fashion_Ramones

8. The Ramones

Converse, the leather jacket, and tight jeans: these are the things, along with three chords, that the Ramones will forever be remembered for. There’s not much else to say, other than this: How many people do you know who own a Ramones shirt but have never heard a Ramones song? — SB

fashion_sexpistols

7. The Sex Pistols

So many of my high school friends have Sid Vicious and Johnny Rotten to thank for their awful high school photos: those liberty spikes the length of stiletto heels, those rank-ass leather jackets pierced through and through with safety pins, those faces permanently posed in some perfect punk sneer. This look has basically been a default uniform for punk kids of the past three decades, and is probably what the Pistols are best known for, more than any one particular song. Which, let’s be honest, is fitting. — SB

debbie-harry

8. Debbie Harry

The blonde behind Blondie is known for her blond hair, yeah, but that’s just the start of it. There was her face, too, with those lips and those so-high cheekbones. But she was perhaps most fashionably impactful in her ability to mix feminine and masculine, throwing a leather jacket over anything and everything. That’s not to sell short her love of t-shirts, either, which was so great as to inspire a feature all about her t-shirts. Punk’s original cool girl lives on, eternally. — SB

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6. Prince

Prince took the shirtless masculinity of ’70s frontmen and made it androgynous in a way that felt crucial. Sequins, ruffled shirts, feminine colors, a big beautiful pompadour, and shockingly tight pants helped him to achieve this sexy look, which he had no problem evolving away from when the time felt right. At the height of his fame, Prince showed off his physique with bare midriffs and assless pants. These days, he’s back to a more conservative look in structured layers, oftentimes accompanied by fantastic hats and necklaces. — JM

fashion_madonna

5. Madonna

Madonna perfected the pop star image pivot, leaving iconic looks along the way. It began with the street style club kid, all thrifted finds, big permed hair, and loads of cheap jewelry. Then the “Like a Virgin” look, still with the jewelry and the perm. Madonna got chic, started wearing bustiers, corsets, and little bodysuits on stage, eventually becoming known for one very specific one: Jean-Paul Gaultier’s cone bra. Since then, Madge’s gone Victorian, Hollywood glamour, Bollywood, bohemian, and much more in between. — JM

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4. The Beatles

The Beatles’ early manager, Brian Epstein, is responsible in large part for the Fab Four’s influence on menswear. He got them out of those greaser leather jackets and pompadours, and into collarless suits from tailor Dougie Millings. Their mop-top haircuts caused riots, but juxtaposed next to drainpipe trousers and Cuban-heeled “Beatle boots,” John, Paul, George, and Ringo still looked somewhat respectable for the era. As time went on, particularly after their India trips to see the Maharishi, the group played with texture, color, and print in a way that embraced the psychedelic experimentation of their mid-career. As the band grew apart, so did their style, which seemed to revert back to menswear towards the end of The Beatles’ tenure. This is captured best on the cover of Abbey Road, where all four are wearing some form of a suit, just in totally different styles, colors, and fabrics. — JM

fashion_gracejones

3. Grace Jones

To start: Grace Jones began this whole thing as a model, and, if nothing else, that pretty much guarantees that she knows how to dress herself. What it doesn’t guarantee, though, is that she would dress herself in ways that were groundbreaking, which is exactly what she did, all while never taking herself too seriously. She’s a classy precursor to Lady Gaga, with her slim, boxy suits and inexplicable hats, among everything else. Oh, and all of those ladies in the ‘80s who were rocking the androgynous look? They’ve got Jones to thank for that, too. — SB

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2. Cher

Cher’s righthand man Bob Mackie has not always steered her towards fashion instead of costumes, and so at this point you expect Cher to wear elaborate outfits instead of separates designed for mere mortals. The wigs, the headdresses, the hippie looks from her Sonny & Cher days, the cascading hair — all of it is crucial but none of it quite compares to the singular, encompassing look in Cher’s style history: the sheer, shimmering get-up that shows off her incredible body. All roads lead back to the glittery, barely-there red carpet dress or bodysuit. Cher’s always used her body as a canvas, rather than fully becoming who the clothes suggest she is. — JM

fashion_bowie

1. David Bowie

Bowie’s clothes have facilitated his shape-shifting personas and dedication to androgyny. His looks are an extension of who he is artistically, and thus, most periods of his work are mirrored in distinct looks: the buttoned-up mod known as David Jones and his subsequent dip into bohemia, the space-age glamazoid Ziggy Stardust, the tailored gender-bending of The Thin White Duke, the hardened edge of Berlin, the Klaus Nomi obsession, the pastels and pleated pants of his 1980s commercial peak, the little goatee and spiked hair of ’90s Bowie, and on and on. Who makes a red mullet, suspenders, platform boots, and an eye-patch look good? How is that even possible?

By partnering with then little-known designers like Kansai Yamamoto (responsible for the look above) and a young Alexander McQueen, Bowie has stayed singular in his style while never really appearing all that interested in the fashion industry itself. He remains an icon for the freaks, and his clothes have always communicated that to the world. — JM