How Rihanna Became the Most Stylish Pop Star of Her Generation

From crystal-encrusted haute couture to pantsless casual looks, Rihanna’s incomparable eye for fashion is an essential part of her art.
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Rihanna in her iconic “naked” dress at the 2014 Council of Designer of America Awards in New York City. Photo by Timothy A. Clary/AFP/Getty Images.

I met Rihanna once. Well, encountered was more like it, though nearly ran smack into her is probably closest to the truth.

It was May 2014, my fourth year working the Met Gala for Vogue. At previous Galas, I had seen Debbie Harry throw on a pink-and-blond punked-out wig and belt out “Heart of Glass,” I sidled past Paul McCartney boogieing with Madonna, and I caught Larry David muttering under his breath about not being able to find a bathroom. In the rarified setting of the Metropolitan Museum of Art after-hours, every sighting automatically becomes surreal. Rihanna, however, was beyond the beyond.

By her own standards, Rihanna’s outfit was pared-down and minimalist that night—a sleek, long-sleeved white crop top and hip-hugging, floor-length skirt, also white, by Stella McCartney. Though we are allegedly the same height, Rihanna had at least four stiletto-heel inches on me. Her hair was piled on top of her head and that made her taller still. She towered, in every sense of the word.

Our impromptu encounter occurred just as people were finishing their final glasses of champagne and beginning to filter out. In a bit, I’d go back downstairs to file any last impressions of the night; Rihanna would head to the after-parties. But we were both observers in that flash of a moment, each of us separately checking out the scene, me mostly struck by her place within and above it.

Her presence really is incandescent: a weirdly radiant charisma, natural and supernatural at once. Here was a star in the actual galactical sense of the word. I didn’t speak to her; there was no time. She disarmed me by suddenly doing something normal and human: She flashed a smile at a friend who ran over and hugged her; she looked happy and she looked incredible. Clothes, it occurred to me then, are perhaps Rihanna’s most convincing disguise, a mask for a person who is a little more than mortal, yet is gracious enough to come and chill with the rest of us now and then.

Rihanna’s Comme des Garçons look at the 2017 Met Gala. Photo by Dia Dipasupil/Getty Images For Entertainment Weekly.

A month later, Rihanna debuted what still stands as one of her most spectacular looks: a sheer, little-left-to-the-imagination, crystal-encrusted dress to accept the Council of Fashion Designers of America’s Fashion Icon Award in 2014. She became the second musician, after Lady Gaga in 2011, to receive the honor (in previous years it went to Sarah Jessica Parker, Kate Moss, Nicole Kidman). At the CFDAs, Rihanna famously freed the nipple (“If I’m wearing a top, I don’t wear a bra; if I’m wearing a bra, I just wear a bra,” she once said) and she did it with supreme class; her look was both daring and original while subtly channeling nearly a century of fashion history. She’d topped it off with a flapper-inspired crystalline turban, a nod to the Jazz Age and fellow sheer frock wearer Josephine Baker who in 1926 challenged notions of race and gender and established herself as the most famous black female performer in the world. Rihanna’s dress also recalled barely embellished gowns worn by Marlene Dietrich and Marilyn Monroe. When a reporter dared query her choice on the red carpet, the singer swiftly shut her down. “Do my tits bother you? They’re covered in Swarovski crystals, girl!” There were no further questions.

At the 2015 Met Gala, her influence was apparent in the wave of sheer dresses that appeared on the red carpet, most notably worn by Beyoncé, Jennifer Lopez, and Kim Kardashian. What Rihanna herself wore to that year’s Gala has become one of, if not the, definitive look in her fashion trajectory. Her Guo Pei egg yolk-yellow robe with a nearly 10-foot long train spilled, waterfall-like, or omelet-like (memes proliferated online almost instantly), over the steps of the Met. Rihanna was of the few guests who hewed studiously to that year’s Costume Institute theme and wore a Chinese designer. She’d done her own research, and sourced the couture piece herself, on the internet—a voluminous, 55-pound, meticulously embroidered robe that had taken Pei two years to make by hand, working solo.

The Met, unlike other red carpets, invites a true sense of the outré—fashion wise, it’s a place where celebrities are given carte blanche to get fully weird. It’s also a place where practical concerns—like stage looks that must be durable enough to withstand maximum twerkage—go out the window. For Rihanna, it opened up another realm of expression—she performs the clothes she wears. “Witnessing Rihanna’s profound enjoyment of fashion is one of the great vicarious pleasures of this era,” Miranda July wrote in a fervent 2015 T magazine profile. “We all detonated the Met Ball in that giant yellow cape.”

It paved the way for her 2017 Met Gala look, in which her figure was surrounded by a fortress of Comme des Garçons rosettes, and for this year’s equally on-topic interpretation of the event’s theme. To co-chair the opening for the “Heavenly Bodies: Fashion and the Catholic Imagination” exhibition at the Met, Rihanna arrived in a towering, silver papal mitier, cape, and minidress by John Galliano for Maison Margiela.

Perhaps most admirable is her ability to do highbrow and lowbrow fashion with equal aplomb, and to pull off a chameleon range of style transformations; Olivier Rousteing of Balmain, one of the first major designers to embrace Rihanna, has compared her to Prince, Michael Jackson, and David Bowie. And as exciting as the Guo Pei couture cape was, we also love the Rihanna who shed it later in the night for a low-cut stage look in which she danced over the tables, singing “Bitch Better Have My Money.”

We love the Rihanna who exudes total glamour, in the silver-embellished, body-hugging dress and the deep red gown she wore to dance through the Hall of Mirrors at Versailles—when she became the first black woman to front a campaign for Dior. But we also love the Rihanna who flaunts a predilection for going without pants whenever she pleases—just a jacket or a hoodie or a T-shirt, thank you very much—whether to the club, on the street, or on fashion front rows. We love the Rihanna who repeatedly Instagrams herself smoking weed; the Rihanna who waltzes out of a restaurant, or an event, or a club, taking her filled wine glass to go—a habit widely documented by fashion blogs and Time alike (and not to her detriment either; this year, Rihanna was named one of the magazine’s Most Influential People in the World).

“Rihanna speaks to her fans with every look,” Anna Wintour said when presenting the CFDA Icon Award. She regularly addresses her 88 million Twitter followers and her 62 million Instagram followers like best friends, dispensing fashion selfies like personal gifts. This is participatory pop stardom: the everyday outfits, the street style, the stage looks, and the Cinderella red carpet moments are theirs too. Within her wardrobe are infinite points of access, places for any of her fans to identify with and claim as their very own. In other words, she is both free enough with herself to fully inhabit a vast and daring range of looks, and generous enough to offer the world a multitude of versions of herself.

The Rihanna you admire most probably says more about who you are than who Rihanna is. Because she is all of it: the thigh-high lace-up boots, the gladiator sandals, the stiletto heels, the sneakers (she is the first female designer ever to win the Footwear News Shoe of the Year award, for her Puma creepers). She is the Gucci balaclava she wore just weeks ago on the desert stage at Coachella, which revealed only her mouth and the flash of her diamante-rimmed eyelashes, and probably made everyone else wishing they were as protected from the crowds as Rihanna. She is also the lingerie as outerwear, the spiked gold minidress, the black leather dresses, the tulle dresses, the sequins and the cut-offs, the hot pants, the curly hair, the straight hair, the red hair, the caramel hair, the hard-edged pompadour, the pixie cut, the waist-length hair, who cares... If there’s anything that unifies Rihanna’s wardrobe, it’s an evident and admirable lack of worry about what others may think of her combined with an alchemical talent for putting together and pulling off looks. As another writer commiserated with me recently, “Talking about Rih and fashion is like trying to talk about god.

From left: Rihanna performing on “The Today Show” in 2011, photo by Jamie McCarthy/Getty Images; at the after party for the Fenty x Puma Spring 2018 collection in 2017, photo by Robert Kamau/GC Images; at the 2009 Met Gala, photo by Dimitrios Kambouris/FilmMagic; at the 2015 Met Gala in her Guo Pei egg yolk-yellow robe, photo by Kevin Mazur/WireImage; at a benefit in New York in 2017, photo by Jamie McCarthy/Getty Images for The New School

Growing up in Barbados, Robyn Rihanna Fenty had a seemingly inborn sense of style. She recalled to Paris Vogue an early childhood memory, when she snuck upstairs during a friend’s birthday party in a pink and yellow swimsuit she’d paired with an African print jacket. There’s a video of what happens next, she swears: “You can hear everyone calling, ‘Robyn, where’s Robyn?’ Then you see these four fingers sliding down the banister as I come downstairs.” She was only 3 or 4 at the time, but she had an instinct for the relationship between fashion and performance; she knew how to make an entrance.

Plenty of divergent style phases would ensue. Young Robyn practiced singing to Mariah Carey, Whitney Houston, Alicia Keys. She found a major early influence in Madonna, whose music and style transformations Rihanna watched closely, particularly attuned to how she “remained a real force in entertainment in the world.” For a while she was into hats and mens’ clothes, sharing jeans and T-shirts with her brother. She got sent home a few times for breaking her school’s dress code, adding piercings or brightly dyed hairstyles to liven up the khaki uniform. (Her Fall 2017 Fenty x Puma collection, with its riffs on deconstructed plaid, would harken back to those years in a mashup of Bad Gal school girl looks.)

When she came to the Def Jam Recordings offices in New York to audition for JAY-Z and L.A. Reid in 2005, Rihanna wore white jeans and a turquoise tube top from Forever 21, and her very first weave. She was 16. She sang “Pon de Replay,” her future hit, and Whitney Houston’s “For the Love of You,” and Reid instructed Jay not to let her leave the building until she had signed a recording contract; she reportedly walked out at three in the morning with a six-album deal.

In photographs from some of her first music industry appearances, Rihanna wears baggy jeans over boxers and crop tops, or silver cowboy boots and denim miniskirts—cute, appropriately teenage, and somehow not fully herself yet. She had landed a contract with one of the most preeminent hip-hop labels in the world, but those early years, she later told Oprah Winfrey, were “claustrophobic.” “They had an idea of who they wanted me to be,” she said to Oprah, talking about her marketing team at Def Jam. “I felt stifled. I don’t even know who I am at 16 or 17.” A couple of years later she had apparently begun to figure it out.

A 19-year-old Rihanna arrived at the 2007 MTV Video Music Awards in a clinging, hot pink strapless mermaid dress and a freshly cropped asymmetric blond-streaked bob to pick up her two trophies. When it came time to perform her hit “Umbrella,” she’d changed into a low-cut black leotard and fedora as if illustrating her song’s lyric (“Good girl gone bad”). This quick-change, suddenly grown-up Rihanna was the first real public glimpse of the star she would become.

It also meant that her most private pain would be unfairly placed on display. When the dark and introspective “Russian Roulette” was released in the fall of 2009, producer Chuck Harmony said that no matter what song she chose as the lead single from her album Rated R, it would immediately be looked at as a song about Chris Brown. Inevitably and unjustly, so would what she wore.

For a brief spell in the months after her ex’s brutal attack, Rihanna was seen in more covered-up looks: a puff-sleeve, tailored Dolce & Gabbana suit to the Met Gala, and elsewhere, another slicked-up suit by Alexander McQueen, accessorized with piles of pearls. But to suggest this signaled a tough new Rihanna would be to give Brown credit he absolutely doesn’t deserve. Rihanna was already tough. If anything, those suits represented a kind of armor against the scrutiny of a gossip-hungry public. Less of her body for the world to see. On the dramatically edgy and stylized black-and-white cover of Rated R, her winged eyeliner, dark lip, leather and cuffs and rings are classic Siouxsie Sioux meets Grace Jones—downtown and gothic, and moodier, yes, but also a natural progression from the fetish looks she’d begun to wear onstage by that point.

With the following year’s “Rude Boy” video, she broke out of every mold. Rihanna sashayed in shades and strappy bondage heels across a bright Basquiat- and Keith Haring-inspired background and went into a litany of costume changes (a one-shouldered number, a gold net bodysuit, a zebra-print catsuit, Rasta-colored fringed hotpants, rainbow-glitter caps and thigh-high leopard-print boots, to name a few).

“In that video you can tell Rihanna is having genuine fun with fashion and remixing it in her own way,” Mel Ottenberg, who would become her longtime stylist, told Women’s Wear Daily. “I knew right then that it was going to happen and be huge.” Rihanna likens their working relationship to a clairvoyant collaboration. “You get me,” she shouted out to Ottenberg from the CFDA podium in 2014. “You honestly get me, and you understand what I’m trying to say. I can send you two pictures, and you bring back the rack full of exactly what I wanted.”

Ottenberg had begun working with Rihanna on the Loud tour in 2011, enlisting his boyfriend Adam Selman and Jeremy Scott, now creative director of Moschino, as designers of that show’s multicolor bikini, metallic blue jacket, and yellow chiffon cutaway dress. But when it came time to make the video for “We Found Love,” whose “hopeless place” was translated on set in Ireland in a dingy bathtub, a skate park, a desolate field, and a fast food joint, Ottenberg dressed his client mostly in his boyfriend’s clothes: flannel plaid, white tank, jean jacket. To this day, both Ottenberg and Rihanna seem to have a shared understanding of when to dial it up, to dial it down, or, to this day, to dial it weird.

From left: Rihanna at the 2011 Grammy Awards, photo by Jon Kopaloff/FilmMagic; at an event in 2005, at the start of her music career, photo by Kevin Winter/Getty Images; her papal look at this year’s Met Gala, photo by Jackson Lee/Getty Images; at a pre-Grammy brunch in 2012, photo by Amanda Edwards/WireImage; at an event 2014, photo by Jon Kopaloff/FilmMagic

It was inevitable, then, that Rihanna would become a designer in her own right, at first in collaborations with Stance Socks, Manolo Blahnik, River Island, and most notably, with Puma. “If the Addams Family went to the gym, this is what they would wear,” she said of her first Fenty x Puma collection. She’d overseen, as she still reportedly does, every fabric, every design. Her black hooded capes, thigh-high lace-up sneakers, black lipstick, grease paint, and crucifixes made for a wardrobe of sporty gothleisure. At the end of the show, Rihanna took the customary designer bow in high-heeled sneakers and a hooded, printed jacket—pantsless, natch.

After she launched her first Fenty x Puma collection, Puma’s sales jumped 92 percent; Rihanna’s core fans, her Navy, form a worldwide, fiercely dedicated sisterhood, whose loyalty translates into dollars too. Her Fenty Beauty line offers foundation for 40 different skin shades—an unprecedented thing in a world still not all that far removed from a time when words like “nude” and “flesh tone” were practically synonymous with “Caucasian.” Fenty Beauty sold $100 million in its first month and provoked emotional testimonials from customers who’d never seen themselves reflected on a makeup counter.

Last week came the arrival of Beach, Please!—the brand’s summer line of tropical- and sand-colored eye shimmers and lip luminizers. And the week of the recent Met Gala saw Rihanna’s Instagram feed veer freely and wickedly from saint to sinner as she alternated between red-carpet shots of her papal look and smoking hot shots of Rih modeling sheer bodysuits and garter belts from her debut line of body-positive lingerie, Savage x Fenty, which recently launched with underwear sizes up to 3XL, and bra sizes up to 44DDD (and more reportedly on the way)—as well as handcuffs and satin restraints in the “Damn” collection.

“I want people to wear Savage x Fenty and think, I’m a bad bitch,” she told Vogue. “I want women to own their beauty.”

Rihanna at the 2007 MTV Video Music Awards. Photo by Jon Kopaloff/FilmMagic.

Rihanna’s most radical act as an artist is her ability to own her fame, to make her autonomy not only creatively daring but commercially viable. Her albums become more unpredictable; her outfits grow bolder. And, as she takes more artistic gambles, she invites her fans to follow suit and take their own risks. She connotes courage and confidence; she reminds them they’re beautiful. In recent years she has grown bolder in all facets of her art, endorsing an appealingly brash, no-fucks feminism. “Bitch Better Have My Money,” her fierce 2015 single was both a prelude to the feminist and protest spirit of ANTI (and a precursor, in its own way, to the entire TimesUp movement). As Doreen St. Felix wrote on this site of Rihanna’s “prosperity gospel,” “Sprawled amongst her earnings, the moneyed black girl is an enlarged version of herself necessarily taking up the space of her debtors, she’s an image of material liberation. There are sell-outs and there are those who turn material wealth into artistic and human power.”

“I got to do things my own way,” she asserts on ANTI, her most unclassifiable album to date. On tour she wore custom-made cutout white chaps and droid-druid hooded looks, which the New York Times dubbed the “hottest club in Tattooine.” On her hit single, “Work,” subversively and irreverently catchy, Rihanna switches into Jamaican patois. Elsewhere the R&B slow burner “Needed Me” doubles as a defiant anticolonialism creed for the British Commonwealth nation of Barbados: “Didn’t they tell you that I was a savage?/Fuck ya white horse and ya carriage.” Wrote NPR: “ANTI is actively telling you, song after song, that it’s not trying to fit.” It’s all emblematic of the multitude of musical and cultural influences in play throughout ANTI: in genre, in language, Rihanna remains powerfully and irreverently on her own terms.

The downside of becoming a fashion force of course is that it can occasionally interrupt the music. Or maybe Rihanna is deliberately keeping the world in suspense. Aside from appearing on “Wild Thoughts” with DJ Khaled and a handful of singles with Future, Calvin Harris, and Drake, she released no new music of her own in 2017. Granted, she’s had plenty else to occupy her too—Ocean’s 8, in which she plays a dreadlocked hacker from the Caribbean, opens this week. But the anticipation for a follow-up to ANTI notches ever upward—in her June Vogue cover story, Rihanna hinted at a reggae album in the making. Till then the Navy has nicknamed the highly anticipated record R9 and its rumored follow-up, R10—terms that, when you think about it, sound an awful lot like the names astronomers use to describe the stars.