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Rihanna's Style Evolution

From the crop top and baggy jeans of her Pon da Replay days to daring bejeweled masterpieces at the Met Gala, Rihanna’s style evolution has seen her transform from cookie-cutter pop star to fashion-forward mega-boss. In honour of entrepreneur, we celebrate Rihanna’s best style moments.

Barbadian musician Rihanna, real name, Robyn Rihanna Fenty, was just 17 when she sashayed onto our screens with the video for her debut single, Pon Da Replay. Confident, bold and oozing with confidence she instantly became a fresh and sassy role model for young women trying to find their voice and feel represented. Little did we know that this rising star would soon dominate in the worlds of music, fashion and beauty with her Fenty empire.

Barbadian musician Rihanna, real name, Robyn Rihanna Fenty, was just 17 when she sashayed onto our screens with the video for her debut single, Pon Da Replay. Confident, bold and oozing with confidence she instantly became a fresh and sassy role model for young women trying to find their voice and feel represented. Little did we know that this rising star would soon dominate in the worlds of music, fashion and beauty with her Fenty empire.

Rihanna’s journey actually began when she was 16, when she signed with Def Jam, counting the power house that is Jay Z and record producer Evan Rogers as mentors. However, while she may have been their protege, her identity was very much her own, becoming a zeitgeist figure not only for her music but also her style.


Her hipster jeans and cropped tops, revealing enviable toned abs, defined that mid-00s era. Yet, in 2006, eager to ditch the young girl persona, Rihanna successfully channeled vintage Hollywood glamour as she made her fashion week debut at New York. Invited to Conde Nast’s annual Fashion Rocks Concert, she dazzled on the red carpet wearing a silver Zac Posen gown, complete with diamonds, establishing herself as a bonafide style icon.


By 2007, three weeks before the release of her critically acclaimed third album, Good Girl Gone Bad, which capitulated her to mega-stardom, Rihanna received her first Met Gala invite. She chose a white gown by Lebanese couture designer Georges Chakra, for the occasion. She’s attended eight Met Galas to date with her most iconic look in 2015 – a show-stopping Guo Pei fur-trimmed empress cape, which featured a 16ft train that reportedly weighed 25kg. The iconic outfit became an instant meme – a true sign of success in the 21st century.


Recognising her clout, attitude and style kudos, designers were eager to collaborate. First up was Gucci. In 2008, Rihanna fronted their Tattoo Heart Unicef campaign. Three years later she was not only modelling collections for Armani Privé (in an ad campaign shot by Mert and Marcus and Steven Klein) but she also worked on the designs. Then in 2014, she was named creative director of Puma under the brand FENTY X PUMA.


That same year, now a record-breaking recording artist, actress, and fashion designer, Rihanna was honoured with the CFDA Fashion Icon Award “for her impact on the industry as fashion’s most exciting ambassador”. The award is given to individuals whose style has made a significant impact on popular culture. Past winners include Lady Gaga and Iman. She collected her award wearing a custom dress by Adam Selman coated in more than 230,000 Swarovski crystals.

However, Rihanna’s reach goes far beyond music and fashion. Having already launched successful fragrances, in 2017 she shook up the beauty industry, launching Fenty Beauty. Focusing on inclusivity and diversity, the collection was lauded for its unprecedented 40-shade foundation range, which has since expanded to include 50 options. The brand was an instant success, earning more than $100 million in the first few weeks, creating a beauty empire in the process.


Fenty continued to make history in 2019 when Rihanna launched her luxury fashion brand in partnership with LVMH Moët Hennessy (LVMH). The deal saw her become the first woman of colour to lead a house for the conglomerate. Unfortunately this month both LVMH and Rihanna announced they have “put on hold the ready-to-wear activity (RTW),” but not before the brand Fenty enjoyed a hugely successful collaboration with Jordanian-Romanian footwear designer Amina Muaddi.


While LVMH and Rihanna won’t be producing any more RTW, with the help of L Catterton, the conglomerate will still support Fenty Beauty and Savage x Fenty. The latter, Rihanna’s lingerie line, “celebrates fearlessness, confidence and inclusivity.” In a post #MeToo era, the Savage x Fenty show, during New York fashion week (September 2019), proved to be empowering, throwing shade on a dated Victoria’s Secret. Rihanna said of the diverse casting, “No matter what shape, size, religion, race, I just wanted women to feel confident and to feel expressive.”


At 33, Rihanna is an imitable legend. She has changed the game in the beauty and fashion industry, ensuring global dominance. More than a style icon, she is a true boss, a fierce leader and a champion of all women.