Rihanna Then & Now: Photos Of The Singer & Fashion Mogul Since Her Start

By:

1 of 31

Rihanna Then & Now

Rihanna Then & Now — Rihanna, the ultimate boss babe, was born Robyn Rihanna Fenty on February 20th, 1988. This Barbados beauty shook up the music scene with her electrifying voice, hitting the charts with a bang after the release of her first hit single “Pon De Replay.”

After 8 Grammy Awards under her belt and cultivating a massive fanbase, Rihanna took her empire to new heights by venturing into the world of fashion and cosmetics. The Savage X Fenty lingerie line, known for its body positivity, made waves and solidified Rihanna as a fashion icon.

Despite being fiercely private about her personal life, the world was ecstatic to hear the news of Rihanna’s pregnancy with partner ASAP Rocky. They welcomed their son in May 2022, and now, with her 2023 Super Bowl performance set to be her comeback moment, Rihanna continues to dominate the game and break barriers.

Check out this throwback pic from 2005, when Rihanna made a statement at the 2006 Spring Baby Phat show during NYFW. Rocking a brown top and chunky jewelry, she was a true trendsetter in the mid-millennium fashion scene.

Ready for more of her best photos? Stay tuned for more stylish snaps of Rihanna through the years.

2 of 31

Rihanna At The NFL Kickoff Celebration

Rihanna At The NFL Kickoff Celebration — Singer Rihanna performs at the NFL Kickoff Celebration Thursday, Sept. 8, 2005, at the Coliseum in Los Angeles. She even wore black tape beneather her eyes!

3 of 31

Rihanna At The 2006 Billboard Music Awards

Rihanna At The 2006 Billboard Music Awards — Rihanna accepts the female artist of the year award at the Billboard Music Awards in Las Vegas, Monday, Dec. 4, 2006. She truly stunned in her white mini-dress.

4 of 31

Rihanna At The MTV Europe Music Awards

Rihanna At The MTV Europe Music Awards — Rihanna performs at the MTV Europe Music Awards at The Bella Centre, Copenhagen, Denmark, Thursday Nov. 2, 2006. She looked great during her performance!

5 of 31

Rihanna At The 59th Bambi Awards

Rihanna At The 59th Bambi Awards — Rihanna poses on the red carpet as she arrives at the 59th Bambi Awards ceremony in Duesseldorf, Germany, 29 November 2007. She wore animal print and waved at photographers.

6 of 31

Rihanna At The 2007 American Music Awards

Rihanna At The 2007 American Music Awards — Rihanna arrives at the American Music Awards in Los Angeles on Sunday, Nov. 18, 2007. She smiled for cameras on the red carpet.

7 of 31

Rihanna performs At Z100 Jingle Ball 2008

Rihanna performs At Z100 Jingle Ball 2008 — Singer Rihanna performs at Z100 Jingle Ball 2008 at Madison Square Garden on Friday, Dec. 12, 2008 in New York. She jammed out in this leather mini-dress.

8 of 31

Rihanna At The 2009 American Music Awards

Rihanna At The 2009 American Music Awards — Rihanna performs at the American Music Awards in Los Angeles on Sunday, Nov. 23, 2008. She seriously rocked out!

9 of 31

Rihanna On ABC’s ‘Good Morning America’

Rihanna On ABC’s ‘Good Morning America’ — Singer Rihanna performs on ABC’s ‘Good Morning America’ in Times Square on Tuesday, Nov. 24, 2009 in New York. She looked great on stage!

10 of 31

Rihanna At The 2009 American Music Awards

Rihanna At The 2009 American Music Awards — Artist Rihanna arrives at the 37th Annual American Music Awards on Sunday, Nov. 22, 2009, in Los Angeles. She posed for the cameras on the arrival carpet.

11 of 31

Rihanna At The 2010 American Music Awards

Rihanna At The 2010 American Music Awards — Rihanna arrives at the 38th Annual American Music Awards on Sunday, Nov. 21, 2010 in Los Angeles. She worked her maroon hair.

12 of 31

Rihanna Visits Capital FM In London

Rihanna Visits Capital FM In London — Rihanna visits Kat Shoob at Capital FM in London on October 1, 2010. She looked like she was totally taking care of business.

13 of 31

Rihanna Performs In Budapest

Rihanna Performs In Budapest — In this picture taken Thursday Dec. 8, 2011, singer Rihanna performs during her concert in Papp Laszlo Budapest Sports Arena in Budapest, Hungary. She looked so confident and glam.

14 of 31

Rihanna Performs At The O2 Arena

Rihanna Performs At The O2 Arena — In this Oct. 5, 2011 file photo, singer Rihanna performs at the o2 arena in east London, as part of her 2011 ‘Loud’ tour. Her fit figure was put on full display in this jeweled outfit.

15 of 31

Rihanna In Northern Ireland

Rihanna In Northern Ireland — Pop star Rihanna arrives for filming in the New Lodge area of north Belfast, Northern Ireland, Tuesday, Sept. 27, 2011. She smiled brightly for cameras.

16 of 31

Rihanna At The Best Buy Theater

Rihanna At The Best Buy Theater — Singer Rihanna arrives for a fan meet and greet at the Best Buy Theater on Tuesday Nov. 20, 2012 in New York. She looked so glam in her all-black look.

17 of 31

Rihanna At T In The Park Festival

Rihanna At T In The Park Festival — Rihanna performs on the main stage during the 20th T in the Park music festival at Kinross on July 13, 2013. She looked great and was totally vibing during her performance.

18 of 31

Rihanna At The 2014 British Fashion Awards

Rihanna At The 2014 British Fashion Awards — Rihanna poses for photographers upon arrival at The British Fashion Awards 2014, in London, Monday, Dec. 1, 2014. She looked so chic in this ensemble.

19 of 31

Rihanna At The 2nd Annual Diamond Ball

Rihanna At The 2nd Annual Diamond Ball — Rihanna attends the 2nd Annual Diamond Ball at The Barker Hangar on December 10, 2015 in Santa Monica. She looked so glam in her gown.

20 of 31

Rihanna At The Christian Dior Paris Fashion Show

Rihanna At The Christian Dior Paris Fashion Show — Rihanna poses for photographers as she arrives to Christian Dior’s Spring-Summer 2017 ready-to-wear fashion collection presented in Paris, Friday, Sept. 30, 2016. She looked gorgeous.

21 of 31

Rihanna At The Launch Of Fenty Beauty In Madrid

Rihanna At The Launch Of Fenty Beauty In Madrid — Rihanna attends the Fenty Beauty by Rihanna Launch on September 23, 2017 in Madrid, Spain. She posed for photos prior to the event.

22 of 31

Rihanna At A Fenty Beauty Event In Paris

Rihanna At A Fenty Beauty Event In Paris — Rihanna poses as she arrives to the Fenty Beauty By Rihanna Paris Launch Party hosted by Sephora at Jardin des Tuileries on September 21, 2017 in Paris, France. Her black mini-dress looked great on her.

23 of 31

Rihanna Celebrates Fenty Beauty’s 1st Anniversary

Rihanna Celebrates Fenty Beauty’s 1st Anniversary — Singer Rihanna arrives at the Fenty Beauty by Rihanna one year anniversary party at Sephora inside JCPenney at Kings Plaza Shopping Center on Friday, Sept. 14, 2018, in New York. She stunned in this ruffled dress.

24 of 31

Rihanna At The 4th Annual Diamond Ball

Rihanna At The 4th Annual Diamond Ball — Singer Rihanna attends the 4th annual Diamond Ball at Cipriani Wall Street on Thursday, Sept. 13, 2018, in New York. She looked stunning in this white ensemble.

25 of 31

Rihanna At The 2019 Fashion Awards

Rihanna At The 2019 Fashion Awards — Rihanna attends the Fashion Awards 2019 at the Royal Albert Hall, Kensington Gore, London, on December 2, 2019. She looked gorgeous in her monochromatic look.

26 of 31

Rihanna at the NAACP Awards

Rihanna at the NAACP Awards — Rihanna accepts the President’s Award at the NAACP 51st Image Awards at the Pasadena Civic Auditorium on Saturday, February 22, 2020 in Pasadena, CA. She gave a moving, inspiring speech.

27 of 31

Rihanna At Savage X Fenty Show Vol. 3 Premiere

Rihanna At Savage X Fenty Show Vol. 3 Premiere — Her own best advertisement! Rihanna attends the premiere of her Savage X Fenty Show Vol. 3 special in New York on Dep. 22, 2021. Her black lingerie made her look irresistible.

28 of 31

Rihanna At The 2021 Met Gala

Rihanna At The 2021 Met Gala — Rihanna stuns in billowing black during the 2021 Met Gala on Sep. 13. The Costume Institute’s annual benefit celebrated the opening of In America: A Lexicon of Fashion that year.

29 of 31

Rihanna At A 2022 Fenty Event

Rihanna At A 2022 Fenty Event — Beauty with a bump! Rihanna shows off her budding baby bump in a green ensemble by The Attico during an event for her Fenty Beauty and Skin brands in LA on Feb. 11, 2022. She announced her pregnancy just weeks prior.

30 of 31

Rihanna Leaves Dior

Rihanna Leaves Dior — Rihanna looks unreal in sheer black as she displays her baby bump after the Dior fashion show during Paris Fashion Week on Mar. 1, 2022. Now that’s a maternity look!

31 of 31

Rihanna At The 2023 Golden Globes

Rihanna At The 2023 Golden Globes — Rihanna was so sexy during the 80th Annual Golden Globe Awards on Jan. 10, 2023. She wore a gathered black gown and had a luxurious shawl draped over her shoulders.

Click to Subscribe to Get Our Free HollywoodLife Daily Newsletter to get the hottest celeb news.

ad