Take a stroll down memory lane as we revisit Rihanna’s most fabulous fashion moments, from her stunning ensembles on the red carpet to her iconic maternity style. This retrospective brings together her unforgettable fashion choices that have captivated the world. Nicole Briese, a valued member of the PEOPLE team since 2022, has lent her talent to numerous publications such as Us Weekly, Brides, and MTV News.

Rihanna has made a significant impact on the fashion industry like few other stars. Prior to launching her own clothing lines with Armani and River Island, she spent years modeling designs from renowned fashion houses on the red carpet. Now, as a successful entrepreneur with multiple clothing businesses under her Fenty company umbrella, she continues to break sartorial records.

In 2015, Rihanna became the first Black spokeswoman for Dior and the first woman to create a brand for luxury conglomerate LVMH Moët Hennessy Louis Vuitton. According to Rihanna, fashion is her ultimate “defense mechanism,” allowing her to compensate for her weaknesses. She believes that fashion should be fun and not frustrating.

Rihanna’s fashion choices have consistently made headlines. From the 50-pound gold Chinese couture gown with a 16-foot train that she wore at the 2015 Met Gala to the voluminous pink Giambattista Valli creation she donned at the Grammy Awards in the same year, her style stands out.

Even during her pregnancy, Rihanna refused to sacrifice her fashion sense. She expressed her aversion to shopping in the maternity aisle, stating that getting dressed up is too much fun to give up just because her body is changing. This mindset is evident in all of her iconic fashion looks throughout the years.

In conclusion, Rihanna’s influence on the fashion industry is undeniable, and her fashion choices continue to captivate and inspire.

During her earliest public appearances, Rihanna often sported a trendy ensemble consisting of a cropped top that exposed her midriff and a pair of low-rise jeans, just like the stylish outfit she confidently rocked at the Teen People Listening Lounge in 2006.

Max Azria was the mastermind behind the elegant blue dress that Rihanna showcased on the red carpet during the 2006 CFDA Awards held in the vibrant city of New York.

Rihanna rocked a stylish ensemble at the 2006 MTV Video Music Awards, where she had the honor of being nominated for the best new artist in a video category with her hit song “SOS.” Her outfit was a delightful combination of chic and playful, featuring a charming flared white mini-dress. To add some extra sparkle, she accessorized it with a dazzling silver belt that perfectly accentuated her waistline. For an extra touch of glamour, mini studs adorned the hem of her dress, adding a subtle yet eye-catching detail to her overall look. Rihanna definitely made a bold fashion statement that night!

The talented musician amazed the audience in New York City during the highly anticipated third edition of the Fashion Rocks Concert. Sporting a dazzling silver dress designed by Zac Posen, she effortlessly stole the spotlight with her elegant side-swept hairstyle and gorgeous deep berry lipstick.

In a mesmerizing bespoke creation by Zac Posen, Rihanna emerged as the triumphant victor of the coveted female artist of the year title at the illustrious 2006 Billboard Music Awards held in the vibrant city of Las Vegas. The enchanting ensemble, adorned in a striking white hue, embraced a gracefully plunging neckline and a beautifully pleated skirt, exuding an undeniable aura reminiscent of the iconic Marilyn Monroe.

During Rihanna’s debut at the Grammys on February 11th, 2007, she gracefully donned an exquisite emerald Roberto Cavalli gown. This stunning ensemble featured a unique side cutout, complemented by a single asymmetric strap.

Rihanna sported a unique ensemble during her memorable “Umbrella” performance at the 2007 MTV Movie Awards. Her outfit included a stylish leather tutu, daring dominatrix pumps adorned with buckles up to her calves, a corresponding leather bra, and a sleek black bob hairstyle.

In Los Angeles, during the 2007 BET Awards, Rihanna exhibited her softer and more delightful persona by donning a strapless white cocktail dress with ruched detailing from the renowned fashion brand Hervé Leger.

Rihanna exuded a timeless charm reminiscent of the classic Hollywood era when she graced the stage at the 2007 World Music Awards. She captivated all eyes with her radiant presence, donning a stunning emerald green gown that elegantly hugged her curves, featuring a mesmerizing mermaid-style skirt.

Riri decided to switch up her attire and opted for a chic, strapless little black dress featuring a playful tulle skirt for her standout appearance at the occasion.

On a pleasant evening in Los Angeles, the renowned singer exuded an effortlessly chic and unconventional vibe as she graced a private dinner hosted by Gucci. Dressed in a tastefully matching ensemble of a Gucci skirt and jacket, her edgy fashion choice caught everyone’s attention. Accompanying her was Joe Zee, former creative director of Elle magazine, adding even more glamour and style to the event. This fashionable outing took place on June 14, 2008, leaving a lasting impression on all who were fortunate enough to witness it.

The “Rude Boy” singer caused quite a stir on the red carpet at the 2008 BET Awards, dazzling everyone in a stunning fluorescent yellow tiered gown personally crafted by the talented Giambattista Valli.

Rihanna flawlessly combined different elements for her appearance at the 2008 MTV VMAs. She skillfully paired a strapless top designed by Patricia Field with a glamorous gold lame miniskirt from Peter Pilotto. To complete her ensemble, she opted for stylish Cesare Paciotti heels.

Rihanna showcased her unique interpretation of the Met Gala’s 2009 theme, which focused on “The Model as Muse: Embodying Fashion.” The multi-talented singer-songwriter made a fashion statement by opting for an androgynous twist, donning a striking Dolce & Gabbana tuxedo. The ensemble, featuring exaggerated ruched shoulders, perfectly encapsulated her bold and confident style.

In 2009, at the AMAs, Rihanna wowed the crowd with her gorgeous black-and-white Marchesa dress. Its origami design, adorned with laser cutout roses, created a truly mesmerizing visual.

Teaming up with Leeora Catalan and the design duo known as The Blonds, Rihanna debuted an edgy and daring sheath dress at her Rated R album release celebration at the Juliet Superclub in New York City in November 2009. Crafted from a robust metal mesh, the dress weighed an impressive 30 pounds. Catalan, speaking to CNN, applauded Rihanna for her courage in sporting such a heavy and unique outfit.

In 2010, Rihanna appeared at London’s Westfield Shopping Centre to bring some holiday spirit by lighting the Christmas lights. She looked stunning in her outfit, donning a stylish gray corset top paired with a vibrant red satin skirt. Completing her festive look, she wore elegant beige pumps, and adorned her hair with a playful polka dot headband. Rihanna’s presence and fashion choices added an extra touch of joy to the occasion.

In November 2010, Rihanna graced the stage at the Europe Music Awards wearing a stunning white corset minidress. This eye-catching ensemble was beautifully embellished with tufted flowers, which added a touch of elegance to the dress, particularly at the hips and back. To complete her regal look, Rihanna wore a sparkling bejeweled crown, effortlessly exuding an air of glamour and sophistication.

The eye-catching dress Rihanna wore to the 2011 Grammys, featuring stunning sheer inlays and intricate white ruffles, was a creation by the creative genius, Jean Paul Gaultier.

In the pleasant month of April 2011, the renowned celebrity adorned herself in a stylish manner to support a noble cause. She chose to wear an elegant Dsquared² dress in a sleek black color with beautiful layers, making a striking appearance at a gathering hosted by DKMS – an acclaimed organization recognized as the global leader in bone marrow donation.

During the 2012 Grammy Awards, Rihanna surprised everyone with her daring and bold fashion choice. The superstar donned a captivating black silk dress by Giorgio Armani, revealing a plunging neckline and a daring center slit. This ensemble was no ordinary outfit as Rihanna revealed it was a collaboration between herself and Mr. Armani. Drawing inspiration from Michelle Pfieffer’s iconic character, Elvira Hancock, in the movie Scarface, Rihanna aimed for a simple yet sexy and slightly gangster look. To complete her alluring attire, she opted for Christian Louboutin heels.

During the Stella McCartney Special Presentation show, the Hollywood actress from Ocean’s 8 mesmerized the crowd with her stunning outfit choice. She confidently showcased her elegant figure in a mesmerizing hunter green slip dress designed by Giorgio Armani. The dress featured a captivating thigh-high slit and delicate straps that gracefully adorned her mostly bare back. To complete her glamorous look, she accessorized with a bold chunky gold choker and opted for enchanting gold eyeshadow that perfectly complemented her stylish Tom Ford sandals.

The songwriter, recognized as one of the most influential individuals by TIME in 2012, graced the prestigious magazine’s gala in an eye-catching hot pink Marchesa gown. The strapless dress featured a unique high-low hem and a playful pointed bustline.

Rihanna playfully mentioned during an interview with Access Hollywood that she needed to keep a firm grip on her attire when she attended the Los Angeles premiere of Battleship on May 10, 2012. She had co-designed the stunning Adam Selman dress, which featured a captivating backless design that exuded sensuality.

Rihanna caused quite a fashion frenzy at the 2012 MTV Video Music Awards with her daring style choices. With her trendy pixie cut and stunning white backless Adam Selman column gown, she made heads turn and sparked intrigue among the fashion-forward crowd.

Rihanna effortlessly showcased her trendy and laid-back style as she stepped out in New York City to promote her highly anticipated album. Sporting a chic ensemble consisting of black leather culottes paired with a sleek and glossy top, the superstar exuded an air of coolness. Completing her fashionable look, she accessorized with a striking gold chain necklace. Unveiling her record at an N.Y.C. Best Buy, Rihanna made a statement not only through her music but also through her impeccable fashion choices.

Rihanna looked absolutely breathtaking at the 2013 Grammy Awards, wearing a mesmerizing Azzedine Alaïa gown that perfectly complemented her long, flowing waves.

Rihanna absolutely dominated the red carpet at the 2013 American Music Awards, rocking a sensational ensemble created by the talented Jean Paul Gaultheir. Her outfit was a killer two-piece, featuring a glamorous sequined bra top and a skirt that perfectly matched, showing off some sheer tulle fabric around her thighs. To add to the excitement, Rihanna’s own mother, Monica Braithwaite, had the honor of presenting her with the Icon Award, a historic moment for the awards show.

The beauty influencer stepped out in a sophisticated and elegant ensemble for the 56th pre-Grammy gala on January 28, 2014. Her outfit choice was a stunning canary yellow shirt dress by Alexander Vauthier, tailored to perfection. The dress featured a silky fabric, a graceful train, a plunging V-neckline, and an ultra high slit that added a touch of allure. Complementing her dress, she wore dazzling gold Louboutins pumps that gleamed with every step. Adding a touch of opulence, her wrist, neck, and fingers were adorned with exquisite Neil Lane diamond jewelry, adding a hint of glamour to her overall look.

Rihanna made a fashion statement at Miu Miu during Paris Fashion Week in 2014 by rocking an oversized Prada leather jacket adorned with a luxurious fur collar and trim.

In 2014, Rihanna sought the expertise of Stella McCartney to craft her ensemble for the prestigious Met Gala. Embracing the theme “Charles James: Beyond Fashion,” Rihanna adorned herself in a stunning white long-sleeve crop top featuring an intricately beaded collar. To complete her captivating look, she paired it flawlessly with a matching maxi skirt, showcasing her impeccable sense of style.

After being honored with the 2014 Council of Fashion Design of America Fashion Icon Award, Rihanna turned heads with her bold fashion choice. The singer donned a stunning gown designed by Adam Selman, which was made entirely of sheer fabric and embellished with over 216,000 Swarovski crystals. To complete the look, she topped it off with a matching headwrap.

In a later interview with Vogue in 2016, Rihanna revealed that she had one regret about her outfit for the event – the absence of a bedazzled thong. She explained that she preferred the dress without any visible underwear, stating, “I just liked it better without the lines underneath. Could you imagine the CFDA dress with a bra? I would slice my throat.” The singer humorously added, “I already wanted to, for wearing a thong that wasn’t bedazzled. That’s the only regret I have in life.”

Rihanna caused a stir as she graced the event wearing a stunning outfit by Tom Ford, who was honored by amfAR in 2014. Her attire featured a white Grecian gown, elegantly displaying a daringly high thigh slit. The ensemble also included a transparent bra adorned with exquisite pink jewels at the bosom.

In 2015, at the Grammy Awards, Rihanna made a stunning appearance on the red carpet. Her choice of attire, a breathtaking Giambatista Valli gown made from silk and tulle, became the indisputable star of the event. With its empire waist and impressive volume, the dress commanded attention and left a lasting impact.

Rihanna achieved a monumental milestone at the Met Gala on May 4, 2015 when she donned a dazzling gold couture gown with exquisite fur trim, which she stumbled upon while browsing the internet. This remarkable work of art was meticulously hand-sewn by renowned Chinese designer Gui Pei over a period of two years, amounting to an astounding 50,000 hours of craftsmanship. Adorned with an astonishing 50 pounds of intricate embroidery and an astonishing 16-foot-long train, Rihanna truly made a lasting impression.

Although the ensemble perfectly aligned with the gala’s thematic focus on “China: Through the Looking Glass,” its extravagance made even the fashion mogul second-guess herself. Reflecting on her iconic look, Rihanna admitted feeling a wave of anxiety as she stepped out of her car, worrying that her outfit was too excessive. Driving past the red carpet, all she could see were conventional gowns, leading her to momentarily doubt her choice, fearing that she may end up looking like a clown, attracting derisive laughter from onlookers.

On the evening of August 28, 2016, Riri made quite the entrance as she made her way to a popular club in SoHo, New York. She effortlessly captivated everyone’s attention with her stunning choice of attire – an exquisite chartreuse fringe gown that boasted elegant sheer panels.

For the 2017 Grammys, Rihanna opted for a striking ensemble created by Armani Privé. The renowned fashion house designed a captivating black plissé ballgown skirt, perfectly complemented by a daring beaded crop top in a vibrant shade of orange. To elevate her look further, Rihanna adorned herself with a plethora of exquisite Chopard jewels that added an extra touch of glamour to her ensemble.

In 2017, Rihanna demonstrated her deep passion for fashion by making a memorable appearance at the Met Gala. She embraced the event’s “Rei Kawakubo/Commes des Garçons” theme with a stunning ensemble that elevated her style game. Rihanna chose an extraordinary multicolored creation from Commes des Garçons’ 2016 runway collection. The three-dimensional piece, inspired by the rebellious punk culture of the 18th century, served as a nod to a time of significant revolutions. To complement her ensemble, Rihanna opted for a pair of elegant lace-up Dsquared2 sandals.

In the year 2017, pop icon Rihanna graced the prestigious Cannes Film Festival with her presence, dazzling the attendees as she walked the red carpet for the highly anticipated premiere of the film Okja. Donning a stunning off-white ballgown courtesy of Dior, she effortlessly exuded elegance and style. To accentuate her glamorous ensemble, Rihanna donned a pair of trendy and diminutive sunglasses from Andy Wolf Eyewear, adding a touch of chic to her overall look.

During the 2018 Met Gala, Rihanna flawlessly portrayed the essence of the “Heavenly Bodies: Fashion and the Catholic Imagination” motif. She graced the event by wearing an embellished strapless mini dress, accompanied by a matching collared robe crafted by Maison Margiela Artisanal. To complete her stunning ensemble, Rihanna adorned herself with a papal mitre, which is commonly worn by bishops during ceremonial occasions. In a conversation with Entertainment Tonight, Rihanna humorously shared her experience wearing the outfit, mentioning how it added extra weight to each step, almost feeling like a squat exercise. She playfully claimed that her posterior even gained some muscle from that night’s fashion extravaganza.

Alexis Mabille Couture designed the stunning white lace bodysuit that Rihanna wore at the fourth annual diamond ball. The outfit included a charming full skirt overlay that gracefully transformed into a bow-shaped top. Rihanna added a touch of luxury by adorning herself with an exquisite selection of Chopard jewelry, elevating her look to new heights.

On the evening of September 12, 2019, the charming hostess dazzled everyone with her radiant presence, emanating a brilliant aura akin to a glistening diamond. She gracefully adorned herself in a stunning black turtleneck gown designed by Givenchy Haute Couture. This exquisite ensemble mesmerized onlookers as the gown gracefully flowed downwards, transforming into a breathtaking white double organza cage skirt.

The female entrepreneur confidently flaunted an impeccably styled oversized suit consisting of a white Jacquemus blazer and trousers. Her sophisticated look was further enhanced by a delightful touch of pink lipstick, adding a perfect pop of color.

In London, during the 2019 Fashion Awards ceremony, Rihanna had the honor of receiving the prestigious Urban Luxe Fashion Award from the one and only Janet Jackson. Being a true fashion icon herself, Janet graced the event in a delightful mint green tube dress from her exclusive Fenty collection. To add that extra touch of elegance, she complemented her ensemble with a matching shawl and adorned her hands with sheer gloves. It was truly a remarkable moment, witnessing the passing of the torch from one style maven to another.

In a stunning fashion statement, Rihanna captivated all eyes at the press conference for the Savage x Fenty Show Vol. 2, held in Los Angeles. She effortlessly exuded confidence, donning a combination of a delicate lace bra, a stylish leather blazer, completed by the addition of gloves and a pair of alluring fishnet stockings. Her captivating presence left no doubt that she had full command of the event.

Maintaining her impressive record of jaw-dropping Met Gala ensembles, Rihanna made quite the entrance at the 2021 event in a magnificent, artistically-designed coat dress by Balenciaga. This oversized masterpiece boasted a striking high collar and a flared hem, truly highlighting Rihanna’s distinctive style.

Adding to the excitement, the gala served as the dazzling red carpet debut for Rihanna and her beau, A$AP Rocky. The power couple displayed an impeccable sense of coordination, as A$AP Rocky sported a vibrant, multicolored quilted blanket ensemble that harmonized effortlessly with Rihanna’s outfit.

In February 2012, Rihanna rocked a vibrant green and pink ensemble from Attico, consisting of a fringed top and pants. The occasion was her appearance for Fenty Beauty and Fenty Skin in Los Angeles, where she casually revealed her baby bump with a game of peekaboo. Expressing her delight, she shared with PEOPLE magazine, “I’m embracing this phase and cherishing the freedom of not constantly hiding my growing tummy. Even if I feel a bit self-conscious, I remind myself that it’s all for the precious little one inside me. Confidence is key!”

When it comes to elevating lingerie into the realm of high fashion, Rihanna always takes the lead. During the Dior fall/winter 2022/2023 fashion show in Paris, back in March 2022, the sensational singer made a bold statement by flaunting a sheer negligee layered atop a delicate lacy bra and thong. Sitting front row, Rihanna proved once again that she effortlessly fuses provocative and elegant styles, leaving the audience in awe of her daring fashion choices.

In a delightful manner, Rihanna embraced the debut of her Fenty Beauty collection at Ulta in March 2022 with an alluring ensemble. She expertly matched a long-sleeved crop top with a playful reveal, adding a touch of sparkle with a dazzling column skirt. Accentuating her pregnancy glow, a delicate silver chain gracefully draped across her midsection, drawing attention to her growing baby bump.

Rihanna made a stunning appearance alongside her partner A$AP Rocky at the highly anticipated premiere of Black Panther: Wakanda Forever. The fashion icon donned a captivating olive green Rick Owens dress that accentuated her figure with its well-fitted bodice and intricate details at the skirt. To complete the glamorous ensemble, she opted for arm-length gloves and elegant pointed-toe olive green heels. Rihanna’s red carpet attire truly turned heads and showcased her impeccable sense of style.

Rihanna took the stage at the Halftime Show in a one-of-a-kind Loewe outfit that was specially tailored to complement the show’s vibrant visuals. The brand explained that the ensemble was carefully crafted to add dimension and flair to the performance. It featured a unique combination of a comfortable jersey catsuit and a skillfully sculpted leather corset, elegantly showcasing her growing baby bump. To complete the ensemble, Rihanna added a stylish layered flight suit made of soft cotton canvas. Adding a touch of glamour, she accessorized with a dazzling 19 carat ruby and diamond ring, along with stunning diamond earrings.

Rihanna stole the show at the 2023 Oscars as she graced the stage in a dazzling ebony attire, comprising a stunning embellished top that beautifully accentuated her growing belly with a glistening array of gems.
To complete her ensemble, the songstress elegantly adorned herself with elbow-length gloves and elegant wide-leg trousers in the same captivating shade. Adding a touch of finesse, Rihanna accessorized with exquisite dangling earrings and a necklace that perfectly complemented her overall look.

Rihanna made a stunning entrance at the 2023 Met Gala wearing a breathtaking white Valentino gown. The dress stole the show with its long train and a hooded cape adorned with 30 silk faille camelias, 500 delicate petals, and 25 graceful leaves.
Adding her own unique touch, the singer sported fingerless gloves that perfectly complemented her outfit. To top it off, Rihanna donned a pair of white cat-eye sunglasses, adorned with oversized false lashes, giving her ensemble an extra flair.