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

By:
Jennifer Phang
1 of 31

Rihanna Then & Now

Rihanna Then & Now
Star Max via AP Images

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.

September 30, 2020, 12:39PM
2 of 31

Rihanna At The NFL Kickoff Celebration

Rihanna At The NFL Kickoff Celebration
AP

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!

September 30, 2020, 12:39PM
3 of 31

Rihanna At The 2006 Billboard Music Awards

Rihanna At The 2006 Billboard Music Awards
AP IMAGES FOR FOX

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.

September 30, 2020, 12:39PM
4 of 31

Rihanna At The MTV Europe Music Awards

Rihanna At The MTV Europe Music Awards
PRESS / Shutterstock

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

September 30, 2020, 12:39PM
5 of 31

Rihanna At The 59th Bambi Awards

Rihanna At The 59th Bambi Awards
Joerg Carstensen/picture-allianc

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.

September 30, 2020, 12:39PM

More AboutRihanna

  • Rihanna Rocks Just An Oversized ‘Use A Condom’ T-Shirt & Boots As She Prepares To Welcome Baby No. 2
  • Rihanna Wears Massive Diamond Toe Ring For Night Out: Watch
  • A$AP Rocky Tells Club-Goers To Calm Down After They Fought In Front Of Pregnant Girlfriend Rihanna: Watch
6 of 31

Rihanna At The 2007 American Music Awards

Rihanna At The 2007 American Music Awards
ASSOCIATED PRESS

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

September 30, 2020, 12:39PM
7 of 31

Rihanna performs At Z100 Jingle Ball 2008

Rihanna performs At Z100 Jingle Ball 2008
ASSOCIATED PRESS

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.

September 30, 2020, 12:39PM
8 of 31

Rihanna At The 2009 American Music Awards

Rihanna At The 2009 American Music Awards
AP

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

September 30, 2020, 12:39PM
9 of 31

Rihanna On ABC’s ‘Good Morning America’

Rihanna On ABC’s ‘Good Morning America’
AP

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!

September 30, 2020, 12:39PM
10 of 31

Rihanna At The 2009 American Music Awards

Rihanna At The 2009 American Music Awards
AP

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. 

September 30, 2020, 12:39PM
11 of 31

Rihanna At The 2010 American Music Awards

Rihanna At The 2010 American Music Awards
AP

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

September 30, 2020, 12:39PM
12 of 31

Rihanna Visits Capital FM In London

Rihanna Visits Capital FM In London
PA Wire/Press Association Images

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

September 30, 2020, 12:39PM
13 of 31

Rihanna Performs In Budapest

Rihanna Performs In Budapest
AP

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.

September 30, 2020, 12:39PM
14 of 31

Rihanna Performs At The O2 Arena

Rihanna Performs At The O2 Arena
AP

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. 

September 30, 2020, 12:39PM
15 of 31

Rihanna In Northern Ireland

Rihanna In Northern Ireland
AP

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. 

September 30, 2020, 12:39PM
16 of 31

Rihanna At The Best Buy Theater

Rihanna At The Best Buy Theater
Evan Agostini/Invision/AP

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.

September 30, 2020, 12:39PM
17 of 31

Rihanna At T In The Park Festival

Rihanna At T In The Park Festival
PA Wire/Press Association Images

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.

September 30, 2020, 12:39PM
18 of 31

Rihanna At The 2014 British Fashion Awards

Rihanna At The 2014 British Fashion Awards
Jonathan Short/Invision/AP

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. 

September 30, 2020, 12:39PM
19 of 31

Rihanna At The 2nd Annual Diamond Ball

Rihanna At The 2nd Annual Diamond Ball
Jordan Strauss/Invision/AP

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.

September 30, 2020, 12:39PM
20 of 31

Rihanna At The Christian Dior Paris Fashion Show

Rihanna At The Christian Dior Paris Fashion Show
AP

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. 

September 30, 2020, 12:39PM
21 of 31

Rihanna At The Launch Of Fenty Beauty In Madrid

Rihanna At The Launch Of Fenty Beauty In Madrid
DyD Fotografos/Geisler-Fotopress

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

September 30, 2020, 12:39PM
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Rihanna At A Fenty Beauty Event In Paris

Rihanna At A Fenty Beauty Event In Paris
Jacques BENAROCH/SIPA

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. 

September 30, 2020, 12:39PM
23 of 31

Rihanna Celebrates Fenty Beauty’s 1st Anniversary

Rihanna Celebrates Fenty Beauty’s 1st Anniversary
Evan Agostini/Invision/AP

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. 

September 30, 2020, 12:39PM
24 of 31

Rihanna At The 4th Annual Diamond Ball

Rihanna At The 4th Annual Diamond Ball
Evan Agostini/Invision/AP

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. 

September 30, 2020, 12:39PM
25 of 31

Rihanna At The 2019 Fashion Awards

Rihanna At The 2019 Fashion Awards
AP

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. 

September 30, 2020, 12:39PM
26 of 31

Rihanna at the NAACP Awards

Rihanna at the NAACP Awards
Associated Press

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.

September 30, 2020, 12:39PM
27 of 31

Rihanna At Savage X Fenty Show Vol. 3 Premiere

Rihanna At Savage X Fenty Show Vol. 3 Premiere
Evan Agostini/Invision/AP/Shutte

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.

February 20, 2022, 1:30PM
28 of 31

Rihanna At The 2021 Met Gala

Rihanna At The 2021 Met Gala
Matt Baron/Shutterstock

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.

February 20, 2022, 1:30PM
29 of 31

Rihanna At A 2022 Fenty Event

Rihanna At A 2022 Fenty Event
Image Press Agency/NurPhoto/Shut

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.

February 20, 2022, 1:30PM
30 of 31

Rihanna Leaves Dior

Rihanna Leaves Dior
Laurent VU/SIPA/Shutterstock

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!

March 29, 2022, 11:20AM
31 of 31

Rihanna At The 2023 Golden Globes

Rihanna At The 2023 Golden Globes
Chelsea Lauren/Shutterstock for

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.

February 7, 2023, 2:25PM
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