Rihanna's Best Outfits: Her Most Iconic Looks Yet
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From her glam red carpet gowns to her head-turning maternity style, here’s a look back at Rihanna's best fashion moments to date
Few stars have disrupted the style industry with as much force as Rihanna.
The singer spent years modeling designs from some of the world's biggest fashion houses on the red carpet (and collaborating on her fair share) before launching her own collections with the likes of Armani and River Island. Now a 10-figure earning mogul with several clothing businesses under her Fenty company umbrella (ella-ella-ay), she's smashing sartorial records left and right.
The first Black spokeswoman for Dior as of 2015 and the first woman to create a brand for luxury conglomerate LVMH Moët Hennessy Louis Vuitton, Rihanna has called fashion her ultimate "defense mechanism."
"I can compensate for all of my weaknesses with fashion," the 2014 CFDA Fashion Icon winner, who showed up to the ceremony dripping in a crystal-covered mesh gown and not much else, said while accepting her award. She added: "Fashion should never be frustrating, it should be fun."
Case in point? The 50-pound gold Chinese couture gown with a 16-foot-train that she walked the red carpet in at the 2015 Met Gala, or the voluminous pink Giambattista Valli creation she wore to the Grammy Awards in 2015.
Even the Oscar nominee's maternity style was a cut above! "When I found out I was pregnant, I thought to myself, 'There's no way I'm going to go shopping in no maternity aisle.' I'm sorry—it's too much fun to get dressed up," Rihanna, who welcomed her first child with A$AP Rocky in May 2022, told Vogue. "I'm not going to let that part disappear because my body is changing."
Below, here are all of Rihanna's most iconic fashion looks to date.
Rihanna at the Teen People Listening Lounge in July 2005
In her earliest appearances, Rihanna could often be seen in a belly-baring crop top and low-slung jeans, like the ones she wore at the Teen People Listening Lounge in 2006.
Rihanna at the 2006 CFDA Awards in June 2006
Max Azria designed the formal blue number Rihanna walked the carpet in at the 2006 CFDA Awards in New York City.
Rihanna at the MTV Video Music Awards in August 2006
Rihanna's look for the 2006 MTV Video Music Awards, where she was nominated for best new artist in a video" for "SOS," was short and sweet, consisting of a flared white mini-dress with a glitzy silver belt and mini studs along the hem.
Rihanna at the Fashion Rocks Concert in September 2006
The Grammy winner stunned in N.Y.C. at the third annual Fashion Rocks Concert thanks to her metallic silver Zac Posen gown, side-swept chignon and berry lips.
Rihanna at the Billboard Music Awards in December 2006
Rihanna took home the award for female artist of the year at the 2006 Billboard Music Awards in Las Vegas in a stunning white custom Zac Posen design with a plunging neckline and a pleated skirt that gave off serious Marilyn Monroe vibes.
Rihanna at the 49th Grammy Awards in February 2007
For Rihanna's first Grammys ceremony on Feb. 11, 2007, she wore a gorgeous green Roberto Cavalli gown with a side cutout and a single strap.
Rihanna performs at the MTV Movie Awards in June 2007
Rihanna's getup for her 2007 MTV Movie Awards performance of "Umbrella" consisted of a leather tutu, dominatrix pumps with buckles all the way up her calf, a matching leather bra and a blunt black bob.
Rihanna at the BET Awards in June 2007
That same month, Rihanna showed off her sweeter side in a strapless ruched white cocktail dress by Hervé Leger at the 2007 BET Awards in Los Angeles.
Rihanna at the World Music Awards in November 2007
Rihanna oozed old Hollywood glamour at the 2007 World Music Awards in her emerald green dress with a mermaid bottom.
Rihanna performs at the World Music Awards in November 2007
For her performance at the event, Riri changed into a short black strapless gown with a flared tulle skirt.
Rihanna at a private dinner in June 2008
The pop star looked edgy and cool in a Gucci skirt and jacket while attending a private dinner by the brand with former Elle creative director Joe Zee in L.A on June 14, 2008.
Rihanna at the 2008 BET Awards
Giambattista Valli constructed the fluorescent yellow tiered gown that the "Rude Boy" singer wowed in on the 2008 BET Awards red carpet.
Rihanna at the MTV Video Music Awards in September 2008
Rihanna mixed and matched her 2008 MTV VMAs look to perfection, pairing a strapless Patricia Field top with a gold lame Peter Pilotto miniskirt and Cesare Paciotti heels.
Rihanna at the Met Gala in May 2009
Rihanna interpreted the Met Gala's 2009 theme of "The Model as Muse: Embodying Fashion" with an androgynous Dolce & Gabbana tuxedo with exaggerated ruched shoulders.
Rihanna at the American Music Awards in November 2009
Rihanna's black-and-white origami Marchesa frock with laser cutout roses for the AMAs in 2009 was a sight to behold.
Rihanna at her Rated R album release party in November 2009
Collaborating with Leeora Catalan and design duo The Blonds, Rihanna brought this spiky sheath dress, which reportedly weighed 30 pounds, to life at her Rated R album release party at the Juliet Superclub in N.Y.C. in November 2009. "It was made of very heavy metal mesh, so kudos to her for wearing it!" Catalan told CNN of the garment.
Rihanna at an event in London in November 2010
Decked out in a gray corset top, a red satin skirt, beige pumps and a polka dot headband, Rihanna was ready to spread some cheer while turning on the Christmas lights at London's Westfield Shopping Centre in 2010.
Rihanna at the Europe Music Awards in November 2010
Rihanna's white corset minidress for her Europe Music Awards performance in November 2010 was adorned with tufted flowers at the hips and back and topped off with a bejeweled crown.
Rihanna at the 53rd Grammy Awards in February 2011
Jean Paul Gaultier was behind the unique white ruffle frock with sheer inlays that Rihanna wore to the 2011 Grammys.
Rihanna at the DKMS 5th Annual Gala in April 2011
The star dressed up for a good cause in April 2011, donning a tiered black Dsquared² dress to an event for DKMS — the world's largest bone marrow donor center.
Rihanna at the 54th Annual Grammy Awards in February 2012
Rihanna wore one of her most daring looks yet at the 2012 Grammy Awards, for which she dreamed up a cut-to-there plunging black Giorgio Armani black silk gown with a center slit. She later admitted the ensemble was inspired by Michelle Pfieffer's character of Elvira Hancock in Scarface.
"This is a collaboration between Mr. Armani and myself," Rihanna told E! News on the carpet. "I helped him design this one. I wanted something … [simple]-but sexy and a little gangster at the same time."
She finished the look off with Christian Louboutin heels.
Rihanna at a Stella McCartney Special Presentation in February 2012
The Ocean's 8 star posed in a slinky hunter green Giorgio Armani slip dress with a thigh-high slit and dainty straps across a mostly open back for a Stella McCartney Special Presentation show. Her chunky gold choker and gold lids also expertly matched her Tom Ford sandals.
Rihanna at the TIME 100 Gala in April 2012
As one of TIME's most Influential People in 2012, the songwriter attended the magazine's gala in a strapless hot pink Marchesa creation with a high-low hem and a pointy bustline.
Rihanna at the L.A. premiere of Battleship in May 2012
Rihanna co-designed the super sexy backless Adam Selman gown she wore to the L.A. premiere of Battleship on May 10, 2012. "I've gotta hold on to my outfit a little tighter than usual," she joked to Access Hollywood of the frock.
Rihanna arrives at the MTV Video Music Awards in September 2012
Between her then newly shorn pixie cut and her elegant white backless Adam Selman column gown, Rihanna caused a serious style stir at the 2012 MTV Video Music Awards,
Rihanna promotes her Unapologetic album in November 2012
Looking cool and casual in a pair of black leather culottes and a shiny black top with a gold chain necklace, Rihanna promoted her latest album release at an N.Y.C. Best Buy.
Rihanna walks the red carpet at the 55th Grammy Awards in February 2013
Rihanna's stunning Azzedine Alaïa gown and long, loose waves struck the perfect note at the 2013 Grammy Awards.
Rihanna at the American Music Awards in November 2013
After slaying the red carpet at the 2013 AMAs in a two-piece Jean Paul Gaultheir design, which consisted of a sequined bra top and a matching skirt with a sheer tulle fabric at the thighs, Rihanna was presented with the awards show's first-ever Icon Award by her mother, Monica Braithwaite.
Rihanna at the 56th Annual Pre-Grammy Gala in January 2014
The makeup mogul's style was all grown up at the 56th annual pre-Grammy gala on Jan. 28, 2014, when she showed up in a silky canary yellow Alexander Vauthier couture shirt dress with a flowing train, a deep V-neckline and a ultra high thigh-slit. Gold Louboutins pumps sparkled at her feet while Neil Lane diamonds iced her wrist, neck and fingers.
Rihanna attends the Miu Miu fashion show during Paris Fashion Week in March 2014
Dressed in a hugely oversized leather Prada jacket with a fur collar and trim, Rihanna kicked off Paris Fashion Week at Miu Miu in 2014.
Rihanna at the Met Gala in May 2014
Rihanna turned to Stella McCartney for her look for the 2014 Met Gala — a white long-sleeve crop top with a beaded collar and a matching maxi skirt — the theme of which was "Charles James: Beyond Fashion."
Rihanna attends the CFDA Fashion Awards in June 2014
As the recipient of the 2014 Council of Fashion Design of America Fashion Icon Award, Rihanna brought the heat, donning a completely sheer Adam Selman gown covered only with Swarovski crystals (more than 216,000 of them) and a matching headwrap to the event. She later cited her decision not to wear a bedazzled thong with the dress as her life's sole regret in Vogue in 2016.
"'I just liked it better without the lines underneath. Could you imagine the CFDA dress with a bra? I would slice my throat," she told the magazine. She added: "I already wanted to, for wearing a thong that wasn't bedazzled. That's the only regret I have in life."
Rihanna at the amfAR Inspiration Gala in October 2014
Wearing 2014 amfAR honoree Tom Ford, Rihanna turned heads in a Grecian white gown design with a super high thigh slit and a sheer bra with pink jewels at the breast.
Rihanna arrives at the 57th Grammy Awards in February 2015
Rihanna's voluminous Giambatista Valli silk-and-tulle gown with an empire waist all but took over the red carpet at the 2015 Grammy Awards.
Rihanna arrives at the Met Gala in May 2015
On May 4, 2015, Rihanna made Met Gala history in an ornate gold couture gown with fur trim that she found online. The stunning piece took Chinese designer Gui Pei two years, or roughly 50,000 hours, to sew by hand and featured 50 pounds of embroidery and a sweeping 16-foot-long train.
Though it was perfect for the evening's theme of "China: Through the Looking Glass," it was so over-the-top, even the fashion powerhouse began to doubt herself. "I remember being so scared to get out of that car because I felt like, 'I'm doing too much,' " Rihanna later told Access of her iconic look. "I was driving past the red carpet and I was just seeing gowns. I was like, 'Oh my god, I'm a clown, people are gonna laugh at me."
Rihanna at a Soho club in August 2016
Riri was a vision in a chartreuse fringe gown with sheer panels while heading to a club in SoHo, New York, on Aug. 28, 2016.
Rihanna walks the red carpet at the 59th Grammy Awards in February 2017
Armani Privé designed a head-turning black plissé ballgown skirt and a bold beaded orange crop top for Rihanna to attend the 2017 Grammys in. She set the look off with Chopard jewels galore.
Rihanna at the Met Gala in May 2017
Rihanna took her love of fashion to new heights in 2017, when she showed up to the Met Gala in an incredible multicolored Commes des Garçons creation that nailed the evening's "Rei Kawakubo/Commes des Garçons" theme. Pulled from the brand's 2016 runway collection, the 3D piece was reportedly inspired by "punks in the 18th century, which was a time of so many revolutions." Rihanna's lace-up Dsquared2 sandals completed the look.
Rihanna at the Cannes premiere of Okja in May 2017
In 2017, Rihanna made her Cannes Film Festival debut, hitting the red carpet for the premiere of Okja in an off-white Dior ballgown and a tiny pair of Andy Wolf Eyewear shades.
Rihanna at the Met Gala in 2018
At the 2018 Met Gala, Rihanna perfectly embodied the "Heavenly Bodies: Fashion and the Catholic Imagination" theme by donning a bejeweled strapless mini dress with a matching collared robe by Maison Margiela Artisinal. A coordinating papal mitre (a ceremonial head-dress of bishops) finished off the spectacular look.
"It was heavy, every step was a squat," Rihanna later said of the outfit in an interview with Entertainment Tonight. "I promise you my butt gained from that night."
Rihanna at the 4th Diamond Ball in September 2018
Alexis Mabille Couture was behind the white lace body stocking ensemble Rihanna hosted the fourth annual diamond ball in, which featured a full skirt overlay that twisted into a bow top. She elevated it even further with a bevy of Chopard jewels.
Rihanna at the 5th Diamond Ball in September 2019
The evening's hostess shone bright like a diamond on Sept. 12, 2019, in a black turtleneck Givenchy Haute Couture gown that cascaded down into a white double organza cage skirt.
Rihanna attends a Fenty Beauty event in Seoul, Korea, in September 2019
The businesswoman showed off oversized suiting done right in a white Jacquemus blazer and trouser ensemble set off by a perfectly pink pop of lipstick.
Rihanna attends the Fashion Awards in London in December 2019
Janet Jackson presented Rihanna with the Urban Luxe Fashion Award at the 2019 Fashion Awards ceremony in London. She wore a mint green tube dress from her own Fenty collection for the occasion, complete with matching shawl and sheer gloves.
Rihanna poses for press at the Savage x Fenty Show Vol. 2 show in October 2020
Wearing little more than a lacy bra, a leather blazer with gloves and a pair of fishnet stockings, Rihanna commanded attention at a press call for the Savage x Fenty Show Vol. 2 taping in L.A.
Rihanna at the Met Gala in 2021
Continuing with her streak of show-stopping Met Gala outfits, Rihanna showed up to the 2021 affair in an oversized sculptural coat dress featuring a high collar and flared hem from Balenciaga.
The gala also marked her red carpet debut with boyfriend A$AP Rocky, who coordinated with Rihanna in a multicolor quilted blanket look.
Rihanna celebrates Fenty Beauty in Los Angeles in February 2022
Rihanna played peekaboo with her baby bump in a green and pink Attico fringe top and pants set for a Fenty Beauty and Fenty Skin appearance in L.A. in Feb. 2012. "I'm enjoying not having to worry about covering up my tummy," she told PEOPLE at the event. "If I feel a little chubby, it's like, whatever! It's a baby!"
Rihanna attends the Dior fashion show in Paris in March 2022
Leave it to Rihanna to make lingerie high fashion. The singer wore a see-through negligee over a lacy bra and thong while sitting front row at the Dior fall/winter 2022/2023 fashion show in Paris in March 2022.
Rihanna at the launch of Fenty Beauty at Ulta Beauty in March 2022
To celebrate the launch of her Fenty Beauty line at Ulta in March 2022, Rihanna paired a long-sleeve peekaboo crop top with a sparkling column skirt. A thin silver chain draped across her stomach highlighted her baby bump.
Rihanna at the Black Panther: Wakanda Forever premiere in October 2022
Rihanna walked the red carpet at the Black Panther: Wakanda Forever premiere alongside her beau A$AP Rocky while wearing an olive green Rick Owens dress with a fitted bodice and structural detailing at the skirt. A pair of arm-length gloves and pointed-toe olive green heels finished off the glam look.
Rihanna at the 2023 Super Bowl Halftime Show
Rihanna performed during the Halftime Show in a custom red Loewe ensemble, which was "designed to build volume in step with the dynamic scenography of the show," according to the brand.
The outfit included a jersey catsuit under a sculpted leather corset, which showed off her baby bump, and a layered flight suit made of cotton canvas.
The singer finished the look with a 19 carat ruby and diamond ring and diamond earrings.
Rihanna at the 2023 Oscars
Rihanna performed at the 2023 Oscars in a shimmering black ensemble, including a glamorous top that highlighted her baby bump with a cascade of jewels.
The singer paired the piece with black elbow-length gloves and wide-leg pants. She then finished off the look with dangling earrings and a necklace.
Rihanna at the Met Gala in 2023
Rihanna arrived at the 2023 Met Gala in an all-white Valentino dress, which featured a long train and a hooded cape covered in 30 silk faille camelias, 500 petals and 25 leaves.
The singer accessorized with fingerless gloves and a pair of white cat-eye sunglasses decorated with huge false eyelashes.
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