Rihanna’s 5 Most Daring & Risqué Fashion Moments
Rihanna turned heads in Barbados at the Crop Over Festival, dazzling in a bejeweled outfit with a matching headpiece and stunning wings. According to TMZ, this was her first time…

Rihanna turned heads in Barbados at the Crop Over Festival, dazzling in a bejeweled outfit with a matching headpiece and stunning wings. According to TMZ, this was her first time at the festival since 2019, making it a big deal.
Rihanna has teamed up with Lauren Austin Designs for her Crop Over looks in the past. “I love working with Rihanna because she’s always pushing fashion boundaries and isn’t afraid to break the rules,” Lauren told Nylon in 2018. “She doesn’t care what others think and wears whatever she wants. She’s an amazing person—easygoing, fun, and friendly.”
Many fans know the singer for marching to the beat of her own drum, especially when it comes to fashion. From glamorous red carpet gowns to eye-catching maternity looks, she’s served up some iconic styles that people still talk about.
In 2015, Rihanna made history as the first Black celebrity to become a Dior brand ambassador. On the red carpet, she told MTV, "It feels fantastic. It is such a big deal for me, for my culture, for a lot of young girls of any color. I think, to be acknowledged by Dior is just... it means a lot as a woman to feel beautiful, and elegant, and timeless."
In 2019, she became the first woman to create a brand under the luxury giant LVMH Moët Hennessy Louis Vuitton. Reflecting on this milestone, she tweeted, “Big day for the culture. Thank you, Mr. Arnault, for believing in this little girl from the left side of an island, and for giving me the opportunity to grow with you at @LVMH.” And of course, we can’t forget the launch of her Fenty empire.
Even while pregnant, Rihanna’s maternity style was on point. "When I found out I was pregnant, I thought, 'There's no way I'm shopping in the maternity aisle.' It's just too much fun to dress up," Rihanna, who had 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."
Many can agree that the singer and beauty mogul has a history of jaw-dropping looks. So, we compiled a list of some of Rihanna's most daring & risqué fashion moments ever. We left out Rihanna's past Crop Over Festival looks because, honestly, they’re just too hot to handle. We didn't want to risk overheating your screen
Take a look below.
2013 American Music Awards - Press Room

Rihanna strikes a pose with the Icon Award in the press room at the 2013 American Music Awards held at Nokia Theatre L.A. Live on November 24, 2013. On stage, she snagged the ‘Favorite Soul/R&B Artist’ of the year award, rocking a stunning Jean Paul Gaultier Spring 2013 Couture two-piece. Her outfit featured a sleek black bustier and a floor-length sheer lace skirt with a girdle-like design. (Photo by Jason Merritt/Getty Images)
95th Annual Academy Awards - Show

Rihanna brought her A-game with not one, not two, but three stunning looks at the 95th Academy Awards. For her performance of "Lift Me Up" from Black Panther: Wakanda Forever, she turned heads in a dazzling black bra adorned with a crystal curtain and sheer mesh straps. She paired it with matching black pants featuring a golden floral design. The look was completed with black pumps, leather opera gloves, layered diamond necklaces, a diamond bracelet over her gloves, and sparkling diamond drop earrings. (Photo by Kevin Winter/Getty Images)
Gucci - Front Row - Milan Fashion Week Exquisite Gucci

Rihanna and A$AP Rocky juggle many roles like music legends, entrepreneurs, and now mom and dad. But no matter what they're up to, they always make a stylish entrance. At Milan Fashion Week 2022, they stole the show at the Gucci runway. Rihanna dazzled in a black leather and lace crop top, topped with a gold headpiece and a bold purple fur coat. Meanwhile, Rocky kept it cool but added a splash of flair with his oversized orange gloves. (Photo by Jacopo M. Raule/Getty Images for Gucci)
amfAR Inspiration Los Angeles 2014 - Red Carpet

Rihanna attended the amfAR LA Inspiration Gala honoring Tom Ford held at Milk Studios on October 29 in Hollywood, California. Rihanna is wearing a Tom Ford Spring 2015 white gown featuring cut-outs, a thigh-high slit, and a sheer bodice with purple embellishments covering just enough up top. This look came shortly after the CFDA Fashion Awards. (Photo by Jason Merritt/Getty Images for amfAR)
2014 CFDA Fashion Awards - Arrivals

Rihanna attended the 2014 CFDA Fashion Awards at Alice Tully Hall, Lincoln Center, on June 2, 2014, in New York City. She was wearing a sheer, crystal-studded gown that left little to the imagination. And by that we mean, nit was nearly nude. She opted for no bra and a skin-toned thong underneath the dress, which was fitting given her style icon status at the event. The outfit was so revealing that Twitter (now X) even removed a tweet she posted showcasing it. (Photo by Dimitrios Kambouris/Getty Images)