But her latest decision - a musical pairing with the man who three years ago left her bloodied and bruised - has left some questioning her judgment.
On Monday, after days of teasing, Rihanna and Chris Brown debuted two songs featuring each other. Brown sings and raps on the remix of Rihanna's sexually charged song "Birthday Cake," and she appears on a new version of his upbeat tune "Turn up the Music."
Rihanna seemed to address the controversy Tuesday when she won best international female artist at the Brit Awards.
"At times when I feel misunderstood, my fans always remind me that it's OK to be myself," Rihanna said.
But Bill Werde, editorial director of the music trade publication Billboard, says Rihanna's decision to make music with Brown could disappoint some of her supporters.
"I think there are people out there that feel betrayed (by) Rihanna," he said. "She has every right to be an individual ... she has every right to date who she wants to date and be with whoever she wants to be with. She's a grown woman.