Rihanna
Rihanna, the former good girl gone bad, has undergone a significant style transformation. She is undeniably considered one of our leading fashion icons—bold, experimental, and a trendsetter for others to follow. In the 2000s, she was a fresh-faced pop star often seen in babydoll tops and cowboy boots.
Fast forward to today, and she has become a formidable force in the fashion world, even launching her brand. In this image, the singer and makeup mogul dons an oversized pinstripe blazer with a cap and gold chains.