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 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.