FASHION

20 Years of Rihanna’s Best Onstage Fashion

In honor of the singer’s music anniversary, we’re looking back at some of her best performance looks over the past two decades.

by Carolyn Twersky Winkler

NEW YORK, NY - NOVEMBER 07:  Rihanna performs during the 2012 Victoria's Secret Fashion Show at the ...
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Oh, how time flies. Twenty years ago, Rihanna released her debut album Music of the Sun, launching the career of one of the century’s greatest pop artists so far. Since then, Rihanna has come quite a long way. In addition to her career as a musician, she’s also added entrepreneur, actress, and mother to her bio. Above all, though, Rihanna is a style icon. And while the focus often remains on the singer’s red carpet and street style, her performance wear is just as notable.

Even when she was paying her dues back in the aughts—performing at every Jingle Ball concert and morning show—she still ensured her wardrobe aligned with her overall vision. While Rihanna’s style has evolved so much, the influences of hip hop and her Caribbean upbringing always remain at its core. Those early days featured a whole lot of low-wasted, stomach-baring mini shorts, but Rihanna quickly moved on, first to girly fit and flare dresses, and then to edgier, leather-clad ensembles. In 2011, when Mel Ottenberg joined Rihanna’s team as her stylist, she experienced a fashion renaissance, turning out some of the most-discussed looks of her career. While the red carpet saw that yellow Guo Pei masterpiece at the 2015 Met Gala or the sheer Adam Selman dress at the 2014 CFDA Awards, the stage saw the custom Zac Posen she wore to her first-ever Diamond Ball, and the red-hot Loewe jumpsuit at the Super Bowl. It’s safe to say Rihanna’s performance style is unmatched. So, in honor of the 20th anniversary of her music, we’re looking back at two decades of the singer’s onstage looks.

2005: World Music Awards

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Rihanna wore a gold mini skirt and cropped white blouse for one of her first-ever live performances, in which she performed “Lose My Breath” during a Destiny’s Child tribute alongside Amerie and Teairra Marí.

2005: Z100’s Jingle Ball

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The singer wore low-cut jeans with her red lace underwear poking out and a tiny tank with a trompe l'oeil green tie to perform at Jingle Ball at Madison Square Garden in 2005.

2006: Teen Choice Awards

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Rihanna took the stage in a white shirt dress, black fedora, and leather gloves at the 2006 Teen Choice Awards after taking home the awards for Choice Breakout Artist and Choice R&B artist.

2006: World Music Awards

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Rihanna went for a more glam look at the 2006 World Music Awards, performing in a draped magenta dress.

2007: MTV Movie Awards

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The singer performed her hit “Umbrella” at the 2007 MTV Movie Awards, though her look was giving more “S&M.”

2007: MTV Video Music Awards

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Rihanna used to love a jumpsuit and fedora, and she got to wear both when performing at the MTV VMAs in 2007.

2007: American Music Awards

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The singer wore a gold bodycon dress at the AMAs in 2007.

2008: Grammy Awards

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Rihanna looked a bit like a sexy scarecrow while performing onstage alongside Morris Day at the Grammys in 2008.

2008: MTV Video Music Awards

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The singer opted for an edgier look, featuring thigh-high, lace-up leather boots at the MTV VMAs in 2008.

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She later changed into a cropped leather jacket, black skinny jeans, and boots that only hit her knees.

2009: American Music Awards

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The singer donned a striped white bodysuit onstage at the 2009 AMAs that couldn’t help but to recall Grace Jones and Leeloo from The Fifth Element.

2010: Last Girl On Earth Tour

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Rihanna might have been performing songs from her album Rated R on the Last Girl on Earth Tour, but the shoulder pads on her jumpsuit would have easily allowed the singer to jump from the stage onto the football field should the need have arisen.

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Clearly, Rihanna was into shoulder pads this tour, because her LED-laced gown also featured the top heavy silhouette.

2010: MTV Video Awards

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Rihanna took the stage in an all-white look to perform “Love the Way You Lie” alongside Eminem at the MTV VMAs in 2010.

2011: Grammy Awards

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She performed the same song in a black and floral gown at the Grammys a year later.

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Rihanna returned to the stage later that night in a fringe and bejeweled set to perform “What’s My Name” with Drake.

2012: Grammy Awards

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While the previous year’s Grammy performance called for a ball gown, Rihanna went much more casual when hitting the award show’s stage in 2012.

2012: Victoria’s Secret Fashion Show

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One of Rihanna’s most iconic performance looks to date is undoubtedly the black Vivienne Westwood dress she wore at the 2012 Victoria’s Secret Fashion Show.

2012: 777 World Tour

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Rihanna’s 777 tour looks were decidedly more casual than her earlier concert fashion.

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The singer belted in a mesh dress featuring a weed leaf at one point during the concert.

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She also opted to stay comfortably in jean shorts and a white shirt.

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This final look from the 777 tour could easily be worn today, 13 years later.

2013: Grammy Awards

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Rihanna wore a sequined striped set while paying homage to Bob Marley alongside Bruno Mars and Ziggy Marley at the 2013 Grammys.

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That night she also donned a slinky black dress to sing “Stay” with Mikky Ekko.

2014: Diamond Ball

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Another classic Rihanna look: the black Zac Posen ballgown she wore to her inaugural Diamond Ball in 2014.

2015: Grammy Awards

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Rihanna suited up in a Maison Margiela double breasted suit alongside Paul McCartney and Kanye West to sing “FourFiveSeconds” at the 2015 Grammys.

2015: iHeartRadio Music Awards

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Nine years before the release of Charli XCX’s Brat, Rihanna wore the now-iconic green color to perform “Bitch Better Have My Money” at the 2015 iHeartRadio Music Awards. The faux fur coat and matching thigh-high boots were both courtesy of Versace’s fall 2015 collection.

2015: Saturday Night Live

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The singer wore an all-denim ensemble to perform “Bitch Better Have My Money” during SNL’s 40th season.

2016: Anti World Tour

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For her Anti World Tour, Rihanna favored a neutral color palette, as seen here with this nude, lace-up bodysuit.

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Off-white chaps belted a gray t-shirt style jumpsuit during the concert.

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The most dramatic look of the tour was a sheer, beaded fringe-covered jumpsuit.

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An olive green oversized suit rounded out the tour looks.

2016: Coachella

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Rihanna had fun spinning around in her fringe jacket when she made a surprise appearance during Calvin Harris’s set at Coachella in 2016.

2016: MTV Video Music Awards

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Rihanna’s performance at the 2016 MTV Video Music Awards featured many outfit changes, but one of the highlights was definitely this pink and white Hood By Air ensemble.

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The trench coat dress she changed into was also a standout.

2018: Grammy Awards

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The singer’s pink, beaded dress was the perfect piece to dance in onstage at the 2018 Grammys, where she performed “Wild Thoughts” with DJ Khaled and Bryson Tiller.

2023: Super Bowl LVII Halftime Show

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Who can forget the red Loewe jumpsuit Rihanna wore for her performance at the Super Bowl Halftime show in 2023?

2023: Academy Awards

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Rihanna doesn’t hit the stage too often these days. The last time we were blessed with a live performance was back in 2023, when the singer donned a Maison Margiela Artisanal look designed by John Galliano to perform her Oscar-nominated song, “Lift Me Up.”