From 2005 to Now: 62 Pictures Charting Rihanna’s Style Evolution

There’s a reason why Rihanna is dubbed the “influencer’s influencer”. The Barbadian singer has always recognized fashion as an extension of oneself, going by her own rulebook and emerging as the trendsetter she is known as today.

With a musical career spanning generations, Rihanna’s first public appearances began in the mid-2000s, which saw the singer finding her feet in the sartorial world. Crop tops, low-rise jeans, and body chains synonymous with the era were favored by her like most in the industry at the time. This may not have led her to stand out then, but did guide her in the direction of what her style would turn out to be. It was when she started with stylist Mariel Haenn, followed by Mel Ottenburg, that her penchant for risk-taking grew and edgy ensembles became her thing. Looking back now, no one but Rihanna could have dared to wear a tuxedo instead of a dress to the Met Gala in 2009, no less her first one. The custom Dolce & Gabbana tuxedo she wore with platform pumps and biker gloves also hinted at her inclination towards menswear which makes appearances even today. The oversized suits and masculine pieces she would wear one day before effortlessly switching to sultry dresses the next, served as the building blocks of Rihanna’s aesthetic.

When stylist Jahleel Weaver joined forces with the star in 2015, Rihanna went on from one viral fashion moment to the next. Not one to restrict her fearless style to a few select brands, she wore pieces by a number of renowned designers including Alexander McQueen, Stella McCartney, Alexandre Vauthier, Roberto Cavalli, Dior, Jean Paul Gaultier, Giambattista Valli, and Givenchy. Talent from the region also found a fan in the star early on, with Rihanna opting for Arab designers for multiple red carpet appearances. Some of her most memorable looks include the white Georges Chakra number she wore to the Met Gala in 2007, the feathered Elie Saab dress at the 2010 Grammy Awards, and the red Alaïa gown from 2013. Whether sitting court side in a sweatshirt dress and bomber jacket or walking into an event in a glamorous gown, Rihanna’s unapologetic sense of style has been a constant. It is one of the reasons why she became the first woman of color to lead an LVMH brand when she launched her brand Fenty in 2019.

As if the fashion world would ever run short of inspiration from Rihanna, the star is serving up more during her first pregnancy. Redefining maternity fashion by still wearing clothes that look and feel very much herself, the mother-to-be has been on a sartorial roll with her show-stopping looks. Her pregnancy reveal look showing off her baby bump through an unbuttoned vintage Chanel puffer will always be remembered, but so will the looks following it. Think baggy denim, belly-bearing tops, statement outerwear, that iconic heart coat, and even a custom Alaïa dress. The low-rise pants and sheer tops in her maternity wardrobe not only serve the purpose of style, but also make the star feel good—and she would argue that that’s what fashion is all about.

Scroll to take a look at Rihanna’s style evolution over the years.

Read Next: Rihanna on Her Maternity Wardrobe: “I’m Enjoying Not Having To Worry About Covering Up My Tummy”