Rihanna wears Guo Pei for 2015 Met Gala

How Rihanna’s Style Has Evolved Over the Years


From Island Sweetheart to Babe in the City, Rihanna is a Style Icon!

Today Rihanna dropped her Savage x Fenty lingerie line and the girlies are excited! Besides her catchy, punchy songs, Rihanna has been many things for us since she hit the scene in 2005. She has been a breath of fresh hair, an unapologetic bad ass, a feminist icon, a sister, a friend, and so much more! While many would argue that the singer turned entrepreneur is not a role model, it’s great to know that she isn’t trying to be anyway. When it comes to beauty and fashion, however, Rihanna is everyone’s trendsetter; remember: “it’s ugly until Rihanna wears it”. To celebrate yet another venture of hers, we decided to recap her style and beauty evolution over the years.


At 17, the Bajan princess emerged on the scene asking the DJ to turn the music up with her debut single, “Pon de Replay“. The vibe of the song was playful and sweet, very much so like the image they wanted her to portray. For the 2005 MTV Video Music Awards, she kept in theme with her cutesy island girl vibe with her casual but cute outfit. Rihanna wore a cropped tank top, sequined vest, white low rise jeans, and black embellished sandals. She was sun kissed and fresh faced with a subtle smokey eye and pink, glossy lips. Her hair was overly coiffed compared to looks we see from her now, but for 2005? It absolutely worked! Side note: who else wore body chains back in the early 2000s?!

Rihanna attends the 2005 MTV Video Music Awards



Many will say that 2007 was a critical turning point for her career. This year began her Good Girl Gone Bad era that included a drastic switch up to her hair. Her hairstylist at the time, Ursula Stephens chopped her lengthy hair into an asymmetrical bob with a side part, and dyed it black! Even if Rihanna wasn’t a bad girl at heart, she sure looked the part with this edgy ‘do. What neither Ursula nor Rihanna could predict was the way that this bob would be the go-to bob for girls looking to cut their hair. Ursula explained that the hit song, “Umbrella” would not have seen the success it did if Rih didn’t switch up her look. We think Ursula might have been right.  


By this point, people had completely bought into the singer’s bad girl image. Rihanna started taking more fashion and beauty risks, and everyone loved it! For the 2008 BET Awards, she wore a lemon yellow ruffled dress with a face framing pixie cut. No one could have guessed this cut would come after the iconic bob, but she owned it! While many stars rocked pixie cuts before her, we can’t help but to opine that Rihanna simply owns every trend she gets her hands on so well that it makes you feel like she started it.


What’s a fashion girlie to wear during her first stint at the Met Gala? Following revelations of her abusive relationship with fellow singer, Chris Brown, the good girl, gone bad had much to prove. In yet another drastic hair move, Rihanna kept her hair cut short, but added a bit more drama by tapering the right side, and adding volume to her side swept bangs. Platinum blonde extensions heralded what would become an experiment in drastic hair color for the singer. Her makeup was just the right amount of drama you would expect from a woman wearing a black pantsuit with exaggerated shoulders, a bow tie, and leather gloves. The charcoal smokey eye and soft pink lips were bold and powerful, a lot like the singer herself.


As mentioned, the blonde streaks she wore in 2009 signaled what would be her most colorful era, Loud! For her fifth studio album, the singer switched her image to something more colorful, fun, and, well, loud. In an unexpected turn, she wore cherry red hair in various styles, including this big spiral curly ‘do. At this point, many realized that Rihanna could be the Madonna of her era, i.e. the princess of re-branding.  


As Tyra Banks once told one of her contestants on America’s Next Top Model, “ghetto, but make it fashion”. When she was honored with the Icon Award for the 2013 American Music Awards, the singer left her house with her hair wrapped and forgot to comb it out! Black girls everywhere would probably never, but once again, Rihanna did it and looked amazing while doing so! Unlike many of the other trends she set, this one didn’t quite catch on, however, we love the rhinestone hair clips that did catch on that year. Her sultry natural smokey eye shadow look, heavily lined under eyes, and nude lips drew just the right amount of attention to her statement hair and outfit. 


In what may still be one of the most talked about Met Gala looks, Rihanna stole the show! The singer committed to that year’s theme, “China: Through the Looking Glass” and wore a one-of-a-kind Chinese couture dress designed by Guo Pei. The handmade dress took two years to make, and was every bit of Chinese luxury if we’ve never seen it before. Keeping attention on her decadent costume, she wore her hair crimson red, with a medium length bob that was flipped at the ends. Not one to ever go over-the-top with her makeup, the most noticeable part of her look was her straight shaped brows. They paired well with her elaborate headpiece and neutral makeup. 10/10, please do it again and again! 


By 2016, Rihanna continued making waves in the fashion industry, this time by signing on to be Creative Director for Puma. She also played a role in the an almost all-female cast for Ocean’s 8. For her role, she rocked locs and looked damn good doing it! Whether or not faux locs are your thing, you have to admit that she wore them effortlessly. 

(Photo by Robert Kamau/GC Images)


That Rihanna reign just won’t let up! In 2017, the singer turned things up a million notches when she launched her Fenty Beauty line. It was highly anticipated and well received – she earned over $100 million in sales during its first month! For her launch party, Rihanna wore her hair in a half/up half down do with subtle waves. Her makeup was all Fenty and as perfect as we thought it would be. She wore a soft lilac eye shadow look, with metallic lilac lips, and soft pink cheeks. Rihanna’s hair and makeup look were cutesy but not like her “Island in the Sun” days. This was the look of someone who was comfortable enough with herself to know that she could rock whatever she want, whenever she felt like it. 


Finally, we have Rihanna in 2018. She started off the year with an amazing performance and win at this year’s Grammy awards for the hit song “Wild Thoughts” featuring herself and Bryson Tiller. We love all things Rihanna and are so excited that she’s branched out into clothing and makeup. To see more of the Bajan beauty’s evolution, watch her Then N’ Now.

(Photo by Kevin Mazur/Getty Images for Savage X Fenty)


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