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2005: MTV Video Music Awards
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Rihanna arrived at her first MTV Video Music Awards shining bright like a diamond in a crop top and glittery vest, paired with low-rise white jeans, and body jewellery perfectly framing her bare midriff.
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2005: Jingle Ball
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It was all about the tight corset tops and low-rise boyfriend jeans for the pop star back in 2005. At Z100’s Jingle Ball concert Rihanna stepped out in a multi-coloured halter neck top paired with low-rise jeans, showing off her matching briefs, and she even added green sneakers to complete the look.
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2006: MTV Europe Music Awards
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Rihanna worked her big hair and killer legs in a Roberto Cavalli sequin mini-dress at the MTV Europe Music Awards.
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2006: Fashion Rocks Concert
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At the third annual Fashion Rocks concert in 2006, Rihanna impressed everyone in a metallic, figure-hugging Zac Posen gown, polished off with an elegant updo and diamond drop earrings.
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2006: Billboard Music Awards
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The recording artist won big at her first Billboard Music Awards, taking home Top Female Artist, Top Pop Artist, and Female Hot 100 Artist of the Year. She even won on the red carpet in this Marilyn Monroe inspired white mini-dress teamed with strappy sandals, a red lip, and perfectly styled straight hair. It’s probably a look we wouldn’t see her in today, but we are loving RiRi’s Old Hollywood glam.
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2007: BET Awards
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The brunette beauty rocked the BET Awards red carpet in a mid-length Herve Leger white dress and a shorter hairdo. She styled the form-fitting number with sparkly Christian Louboutin pumps and drop earrings.
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2007: 49th Annual Grammy Awards
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Rihanna first made her mark on the Grammy’s red carpet in 2007 when she wore this stunning Roberto Cavalli cut-out gown. She teamed the emerald green pleated masterpiece with matching bracelets and debuted another new haircut.
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2008: American Music Awards
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At the American Music Awards in 2008, Rihanna took home two awards and looked fierce in a black leather ensemble. Channeling her hit “S&M”, Rihanna sizzled in a skin-tight spiked corset, leather pants, and over-the-knee boots. We see another new hairstyle from the singer with this darker, shorter ‘do.
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2008: BET Awards
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The Barbados native absolutely stunned in a Giambattista Valli tiered chiffon gown at the 2008 BET Awards. She paired the playful dress with another new hairstyle - but this time, it’s an adorable pixie cut.
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2009: American Music Awards
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Looking like her fiery self, Rihanna hit the AMA red carpet in an architectural, floral cut-out Marchesa gown. She paired the statement ball gown with white pumps, and added her signature winged eyeliner and nude lip to complete the look.
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2009: 'Inglourious Basterds' Premiere
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Rihanna stepped up her fashion game for the London premiere of "Inglourious Basterds" in 2009. The Bajan beauty oozed glamour in an Alexander McQueen jumpsuit, lace gloves, and dripped in an array of pearl necklaces. She finished off the look with a sky-high faux-hawk hairdo and a glossy red lip.
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2009: Met Gala
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Sticking to the black suit theme, Rihanna arrived at the “Model as Muse: Embodying Fashion” 2009 Met Gala in a puff-sleeved Dolce & Gabbana silk tuxedo. She added a bowtie, leather gloves and blue winged eye-shadow to complete the mesmerizing look.
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2010: MTV Europe Music Awards
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At the MTV Europe Music Awards in 2010, Rihanna was the epitome of beauty in a Marchesa gown, comprised of ruffles and delicate swirls. Plus, her stunning red hair teamed perfectly against the cream-coloured number.
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2010: 52nd Annual Grammy Awards
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Rihanna was a vision in white at the Grammy Awards in 2010. The recording artist made all the best-dressed lists in this high-collared Elie Saab Haute Couture gown, with chiffon and feather detailing gracing the bodice. She finished off the breathtaking look with Neil Lane jewels, a faux-hawk, and white eye-shadow, adding to her flawless makeup.
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2011: 53rd Annual Grammy Awards
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A year later, the pop star stunned again in white at the 2011 Grammy Awards. This time, Rihanna left little to the imagination in a Jean Paul Gaultier sheer panelled gown. She let her red locks loose, matching it to her lipstick, which amped up the scandalous look.
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2012: Time 100 Gala
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The starlet was honoured at Time magazine’s 100 Most Influential People in the World gala in an ultra-feminine Marchesa gown. She styled the high-low strapless number with Christian Louboutin black pumps, long dark curls and dangly diamond earrings – we can’t get enough of Rihanna’s girly side!
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2012: 54th Annual Grammy Awards
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Another Grammy Awards, another hairstyle and stellar look from the pop star. Rihanna stepped out in a daring ensemble in this plunging Giorgio Armani silk gown, complimented with a thigh-high slit and delicate train. The blonde-haired beauty added gold jewellery, and a Jimmy Choo clutch to finish off the luscious look.
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2013: American Music Awards
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At the American Music Awards in 2013, RiRi showed off her amazing figure in a glittering bra top and sheer skirt, highlighting off her many tattoos. She added a crystal-embellished choker and ear cuff to the jaw-dropping look. Her brunette locks were slicked back, letting the daring ensemble speak for itself.
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2013: 55th Annual Grammy Awards
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Rihanna was a vision in red at the 2013 Grammy’s, wearing a custom Azzedine Alaia slightly sheer gown. She kept the accessories minimal, letting the criss-cross flowing gown take center stage. But, she pulled the whole look together with her long curls perfectly framing her flawless face.
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2014: The Diamond Ball
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At Rihanna’s inaugural Diamond Ball, she was sure to make an entrance in this rose-coloured, Zac Posen satin gown. She completed the mermaid masterpiece with a stunning Chopard pear-shaped diamond necklace, and a slicked back ponytail.
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2014: CFDA Fashion Awards
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CFDA Fashion Icon Award-winner Rihanna turned-heads in one of her most daring looks yet, wearing a custom Adam Selman fishnet dress that featured over 216,000 Swarovski crystals. She added a pink fur shawl and extra jewels to complete the jaw-dropping ensemble.
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2014: Met Gala
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For the “Charles James: Beyond Fashion” Met Gala, Rihanna showed off her toned midriff in a simple, yet stunning Stella McCartney crop top and floor-skimming skirt ensemble. The singer styled her dark locks in a wavy updo, and added silver rings to complete the striking look.
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2015: 57th Annual Grammy Awards
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Although she made many of the worst-dressed lists at the 2015 Grammy’s, we’re still praising Rihanna’s ruffle-filled statement dress. The singer looked ultra-pretty in this Giambattista Valli princess gown, paired with Chopard jewellery and a simple, yet chic bun.
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2015: Met Gala
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Rihanna did not disappoint as she channeled the theme of “China Through the Looking Glass” at the 2015 Met Gala. The singer should “Take a Bow” for her mesmerizing fur-trimmed cape, that took two years to create by Guo Pei. The Barbados babe even added a metal hair piece to complete the show-stopping look.
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2017: 59th Annual Grammy Awards
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While making her way down the Grammy Awards red carpet in 2016, Rihanna returned in another eye-catching look. The Caribbean queen let her brunette locks loose and wore an Armani Prive sparkly orange crop top paired with a full black skirt.
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2017: Fenty Beauty Launch Party
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Rihanna celebrated the launch of Fenty Beauty looking like a real-life doll in this lilac, tulle mini-dress by Molly Goddard. She added Rene Caovilla silver strappy heels and Chopard jewels to add to the princess-inspired look. And of course, the singer looked flawless in purple-hued makeup from her very own beauty line.
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2017: 'Valerian And The City Of A Thousand Planets' Premiere
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RiRi stunned in a whimsical number at the “Valerian and the City of a Thousand Planets" premiere in Hollywood. The singer looked pretty in pink in this Giambattista Valli Couture gown, completed with a flowing train. She added delicate diamond hoops and custom Manolo Blahnik lace-up heels to complete the refreshing look.
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2018: Met Gala
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For the fashion event of the year, Rihanna did not disappoint in another iconic Met Gala look, inspired by the theme: “Heavenly Bodies: Fashion and the Catholic Imagination”. The “Diamonds” singer took her Catholic imagination to the next level, stepping out in a Pope-inspired hat and bejeweled mini-dress, that featured a built-in skirt. Her ornate look was accompanied by matching Christian Louboutin pumps and Cartier diamonds.
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2018: The Diamond Ball
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The singer held her fourth annual Diamond Ball, looking angelic in an Alexis Mabille lace jumpsuit, with an oversized bow perfectly covering her bust. She accessorized the bold look with Jimmy Choo pumps, and an assortment of Chopard jewels – her favourite!
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2018: Fenty Beauty One-Year Anniversary Celebration
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Just days later, Rihanna sizzled in hot pink dress at Fenty Beauty’s one-year anniversary party in New York. The singer wore a custom Calvin Klein ruffled creation, that featured a thigh-high slight and matched perfectly against her pink-hued makeup.
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