Rihanna Best Outfits and Fashion Moments in History

Rihanna has singlehandedly heralded a new era of maternity style, broadened the scope of inclusive brands with her Savage x Fenty line, and made history as LVMH’s first Black woman designer in 2019. Her career in fashion is worthy of every accolade, but her style is more personal. It represents the 35-year-old Barbadian musician’s ability to think for herself, and convey a message through her clothing.

She did this by pioneering the naked dress trend in Adam Selman at the 2014 CFDA Fashion Awards, where she was recognized as fashion icon award winner. She followed up in a strategically unbuttoned pink Chanel puffer coat to announce her first pregnancy with partner A$AP Rocky. And at the Super Bowl LVII halftime show, she reminded us that she’ll stay true to her signature brand of edgy-athleisure in a Loewe utility jumpsuit with a vinyl breastplate, positioned just above her growing belly to subtly confirm baby number two. While she works with renowned stylist Jahleel Weaver to dream up many of her outfits, there is no denying Rihanna’s input as both a collaborator and artist. Other gigs throughout her past — she was named creative director of Puma in 2014; fronted campaigns for Armani, Balmain, and Dior; and developed collections with Manolo Blahnik, Chopard, and Amina Muaddi — endorse her longstanding status as a trendsetter.

Following the star’s performance of “Lift Me Up” at the 2023 Oscars where she wore a Maison Margiela by John Galliano look dripping in crystals, she changed into a seafoam-green Bottega Veneta ensemble backstage that went under the radar. While others scurried to the Vanity Fair red carpet, Rihanna showed off her notable coordination with A$AP Rocky as he cradled her bump, complementing her color palette in a buttercream tuxedo that only further highlighted yet another one of Rihanna’s style visions come to life.

Ahead, scroll through time and count down Rihanna’s best fashion moments to date.