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Rihanna's Best Fashion Moments

Fifty reasons why she won the CFDA Fashion Icon of the Year award.

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By Celia L. Smith · June 3, 2014

Rihanna's fearless fashion sense and the attitude in which she carries her style is exactly why she was recognized by the Council of Fashion Designers as the Fashion Icon of The Year. At the award ceremony the singer's Adam Selman designed, Swarovski crystal embellished, see-through gown and matching head scarf stole the show, channeling the late great Josephine Baker.

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Rihanna was so in love with last year's punk theme, she re-lived it again this year. The singer donned a white bold shoulder cropped top and ruched floor-length skirt by Stella McCartney.

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While Rihanna's doobie wrap was the center of attention at the American Music Awards it was her Jean Paul Gaultier bead and lace brasierre style gown that caught our attention.

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When it came time to accept the Icon Award onstage at the AMA's, Ri-Ri opted for yet another sexy JPG gown.

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The singer softened up her style in a sheer Azzedine Alaia gown at the GRAMMY Awards that appeared as if she rose from the red carpet.

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There was no other way for the singer to kick off her Diamonds world tour, than by shining bright in this custom Lanvin jumpsuit.

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Rihanna gets raunchy in embroidered hot pants and matching coat, a leather bra top to rival Madonna's and thigh-scraping lace-up boots, all by Givenchy.

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Before Olivia Pope made white coats popular, Rihanna worked the crowd in Morocco sporting an oversized Miu Miu style, with Lanvin accessories and Gianvitto Rossi knee-high boots.

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In Singapore Ri-Ri brightens things up, ironically in a Raf Simons look from his Spring '13 men's runway. If anyone could pull it off, she can.

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In Middle East garb with an urban twist, Rihanna performs on stage at Abu Dhabi wearing white layers of the Kokon To Zai menswear collection.


Heading out with friends for the night in London, Ri-Ri doesn't rock just any typical baseball style bomber, hers is a seriously hot Roberto Cavalli style.


The singer takes her most talked about hair style off the red carpet and onto the streets with a Torn By Ronny Kobo dress and Giuseppe Zanotti thigh-high boots.

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Rihanna was court-side chic on Christmas day in a black cropped top and black skinnies, accented by a gold Christian Lacroix choker, body chain and Manolo Blahnik heels.

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Layered in her own line (Rihanna for River Island) and Versace glasses, the singer hits the Miami streets.

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The singer can't be missed in a cherry red Zac Posen style with goth style creepers and a choker.

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In full-on 90s-inspired regalia, Ri-Ri walks the street risqué in a crush velvet Rihanna for River Island "playsuit" and thigh-high suede boots.

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On a night out dining at Nobu, the singer was spotted wearing the jumpsuit of all jumpsuits: Balmain's leather with gold hardware style with matching metal-tipped boots, straight off the runway.

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Cropping it like it's hot, the diva dons a Versace look from the resort '14 runway collection with matching Manolo Blahnik's for the opening of the new M.A.C cosmetics store in Hong Kong, China.

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The singer serves style with severity in a River Island bodycon she designed that's sure to make anyone run to buy it.

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Rihanna's a global girl and she's wearing it loud and proud in a flag printed Kokon To Zai oversized T-shirt and drop crotch trousers, a Vivienne Westwood clutch and lugged sole boots while hitting the streets of London.

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After the show it's the after party, and Rihanna was spotted leaving one the morning after the VMA's in a bodycon Balmain and her signature Manolo Blahnik sandals with cocktail in hand.

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We love that Rihanna rocks pieces straight off of the men's runway. In London, the singer channels her inner David Bowie with this checkered Saint Laurent moto jacket and mullet cut complete with Manolo's for a ladylike finish.

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In full-on 90's nostalgia style, Rihanna sits front row at the Opening Ceremony show in a silver paisley print Zac Posen dress with Agent Provocateur tights and creeper shoes by Underground.

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Repping her River Island collection again, the singer is feeling fashion fatigue while casually dining at Da Silvano's.

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Mary Kantrantzou's playful butterfly tunic and Tom Ford gladiator sandals make one killer combo for a night on the town.

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Rihanna takes to the streets in whatever she pleases, this time it's a Roman-inspired look disguised in a another backwards cap, Chanel shades and necklace and Rihanna for River Island cut-out boots.

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At the launch of Rihanna's clothing and shoe collection for River Island in London, the singer opted to wear the sexiest piece of all –– a high split bodycon with her favorite Manolo heels.

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On a girlier note, Rihanna rocks a full Balmain look in a robin's egg blue shade fit for Easter day.

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Even filming a Budweiser commercial is a fashionable fete for Ri-Ri. The singer donned a cropped jacket, knit pencil skrt and Azzedine Alaia shoes for a look that was utterly chic.

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In head-to-toe Chanel, the singer looks like the chicest school girl there ever was while patrolling the streets of Paris.

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The singer's too-cool-for-school overalls and pumps is a definite Sex And The City style moment.

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Only Ri-Ri could make one of the simplest ensembles look cool, like this leather T-shirt paired with ridiculously fly Tom Ford boots.

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This "Ri-Ri Woo" red, high-gloss Miu Miu skirt was a traffic stopper in Manchester.

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Dark and moody was the vibe behind this Kokon To Zai menswear-inspired look and Silver Spoon beenie –– an ode to London grunge.

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The singer pays homage to real street style with a few classics: an oversized Adidas sweatshirt, bandana and Ray Ban Wayfarers.

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Rihanna photo bombs photographers in a bright blue lipstick and a bomber jacket we'd rock from Rihanna for River Island SS14 collection.


This clean summer-white ensemble and saddle-colored visor worked perfectly across the pond for Rihanna.

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Rihanna clearly isn't afraid of being completely transparent with her fans and this Adam Selman mesh short set proves it. Balenciaga sneakers and Prada sunglasses takes the singer's summer white style to new heights.


Riri arrived on the red carpet of her flick Battlefield in Sydney, Australia wearing a clean lined Stella McCartney jumpsuit, gold hoops and Manolo Blahnik sandals.

In true London fashion, Rihanna sports a psychedelic tuxedo blazer by Brit designer Stella McCartney. She paired this look with Barton Perreira Kevin sunglasses and her favorite ankle strap sandals by Manolo Blahnik.

At the 2012 Victoria's Secret Fashion Show the singer naturally chose a sexy lingerie look for the stage in a girly pink see-through nighty with a white panty and bra set.

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Sexy, stunning, and bold was Rihanna's Armani gown at the 54th Annual GRAMMY Awards in 2012. Hands down, best dressed and most buzzed about look of the night.

We went gaga for Rihanna's burlesque stage style at The 2012 Victoria's Secret Fashion Show in New York City. It was over-the-top but that was everything we loved about it.

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Clad in Karl Lagerfeld's designs, Rihanna attends the Chanel show as part of Paris Fashion Week Haute Couture Fall/Winter 2013-2014 at Grand Palais in Paris, France.

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At the 2012 BRIT Awards the singer sparkled in a Givenchy crystal gown and leather opera gloves in London.


Rihanna owns her edgy bad girl style and works it. We can always count on her to kill the red carpet in something sexy — like this exotic Tom Ford croc style or a see-through, backless and plunging number.

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Things get prim and proper for Rih-Rih at a Chanel fashion show in Paris. A lovely shade of lavender from cropped top to kicks, complete with pearls on her wrist courtesy of Chanel.


Rihanna decked in Dior; a bold red fur, satin dress, and thigh-highs with all of the right accessories at the Christian Dior show in Paris.


At eco designer Stella McCartney's fashion show this season, the singer sits appropriately in an envious shade of green from Stella's collection with cat-eye sunnies to complete her catty look.

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The singer poses in a menswear-inspired Lanvin look we love, with none other then the Lanvin designer himself, Alber Elbaz

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