Described as a "young Rockafella recording artist", the Barbadian ingenue arrives at the Teen People Listening Lounge hosted by Jay-Z in 2005. Wearing baggy stone-washed jeans peeping her boy shorts and hair that screams TREsemme beachy waves, RiRi hasn't yet developed a notable fashion sense.
Rihanna looking not so rocking at the...
Rihanna looking not so rocking at the "Hope Rocks" benefit concert in 2005. Jean skirts on a red carpet never work, especially when combined with baby-doll lace and silver cowboy boots; sort of cute, very confused.
For Rihanna's first appearance on MTV...
For Rihanna's first appearance on MTV's TRL in September, 2005 she seems even more confused-- embroidered boot cut pinstripes over Chucks and a saber-tooth rosary necklace? This is like a Nickelodeon series meets an archeology expedition. At least MTV brought out the curling iron.
Rihanna swaps her jean skirt for some...
Rihanna swaps her jean skirt for something a little more appropriate at the 3rd Annual Vibe Awards in Los Angeles. Girlish and cute, RiRi rocks a baby-doll look with an awkward accessory choice. She's starting to look a tad more refined.
2006: 360. Rihanna films a video for ...
2006: 360. Rihanna films a video for her first #1 hit, SOS, and starts to move from good girl towards an eventual good girl gone bad. An angular hair-cut combined with tight black is a hint at what's to come.
After SOS, the cuteness factor is rep...
After SOS, the cuteness factor is replaced with something a bit more polished. Thigh-high boots, smart accessories, and a particular color scheme replace a hodge-podge of jewelery and youthful clothing choices.
Designers start to catch on Rihanna's...
Designers start to catch on Rihanna's statuesque beauty. Not high-fashion quite yet, RiRi shows up at the MTV Music Awards in Japan in a whimsical yet sophisticated Foley dress.
This time around on TRL, Rihanna is p...
This time around on TRL, Rihanna is prepared to wow. Dressed in Dolce & Gabbana neon with Giuseppe Zanotti heels, RiRi gets sultry on the piano.
Making an appearance at Conde Nast's ...
Making an appearance at Conde Nast's Third Annual Fashion Rocks, Rihanna wears a flattering Zac Posen gown accentuating her curves. RiRi steps away from her teenage appeal into something a little more mature.
Rihanna's last flirtation with soft, ...
Rihanna's last flirtation with soft, long curls. Her stage outfits become more risque in the spirit of Miss Aguilera a la Back to Basics.
2007: At the 2007 Grammy Awards, RiRi...
2007: At the 2007 Grammy Awards, RiRi sports this Roberto Cavalli diaphanous green dress. Her fashion sense is refined yet adventurous. RiRi's hair progressively gets shorter and more geometric.
Rihanna's hit "Umbrella" made a huge ...
Rihanna's hit "Umbrella" made a huge splash and vaulted RiRi to Diva status. At the 2007 MTV Movie Awards, Rihanna sports an asymmetrical bob and plays with a wardrobe alluding to bondage softened with lace.
Playing up the lace-bondage homage to...
Playing up the lace-bondage homage to Madonna, Rihanna's look is still soft but more conscious of the statement she can make with her wardrobe.
Rihanna starts to always appear on an...
Rihanna starts to always appear on and off the carpet in the hottest trends and designers. Here she poses in Tokyo during the Live Earth concerts in a D-Squared Halter Jumpsuit and Christian Louboutin pumps.
In addition to fashion designers taki...
In addition to fashion designers taking notice, Venus Breeze declares that Rihanna has the best legs in America in 2007. Named 'Celebrity Legs of a Goddess', Rihanna sports a sleek skirt and tank with her popular 'umbrella' bob.
RiRi pays homage to old Hollywood wit...
RiRi pays homage to old Hollywood with her curled bob and tightly draped Dolce & Gabba gown.
2008: This Egyptian inspired Mara Hof...
2008: This Egyptian inspired Mara Hoffman dress from her Fall 2008 collection inspired some naysayers. By the looks of this picture, I'm not sure if Rihanna was feeling the print much either.
Rihanna plays with color in this Giam...
Rihanna plays with color in this Giambattista Valli ruffle gown at the 2008 BET Awards in Los Angeles. Her cute new boy-crop with side-swept bangs makes her look like a pixie.
Rihanna arrives at the 2008 American ...
Rihanna arrives at the 2008 American Music Awards in a Zac Posen asymmetrical dress. Her accessories are minimalist yet perfect. She performs Rehab at the ceremony outfitted in a Diamond encrusted eye-patch.
2009: Wearing Arampali jewels and a J...
2009: Wearing Arampali jewels and a Jasmine di Millo ruffled tulip dress, Rihanna attends the RIAA and Feeding America Inauguration Charity Ball in Washington DC.
Rihanna in a watercolor Gucci gown fr...
Rihanna in a watercolor Gucci gown from the Spring 2009 collection. Later this evening drama ensues between beau Chris Brown and RiRi, leaving her badly beaten and abused.
Rihanna remerges in May of 2009 after...
Rihanna remerges in May of 2009 after the abuse in February. Rihanna alters her signature look to something more masculine and hard in this geometric and shouldery Dolce & Gabbana suit.
Colder and calculated-- Rihanna sport...
Colder and calculated-- Rihanna sports an ominous Alexander McQueen Pre-Fall Jumpsuit and Masion Martin Margiela shoe boots at the UK premier of Inglorious Bastards.
Rihanna is Karl Lagerfeld's darling a...
Rihanna is Karl Lagerfeld's darling at Channel's Paris Fashion Week Spring/Summer 2010 show. She, of course, wears head to toe Channel and replicates Lagerfeld's signature cheeky frown.
Looking like Grace Jones at Andy Warh...
Looking like Grace Jones at Andy Warhol's memorial, Rihanna visits Alexa Chung in a frighteningly pricey Alexander McQueen asymmetrical dress. Still shaded, at least smiling.
Rihanna appears on the red carpet wea...
Rihanna appears on the red carpet wearing a cut-out black and white Marchesa dress with orange hair at the 2009 American Music Awards.
Rihanna also sports cut-outs during t...
Rihanna also sports cut-outs during the 2009 AMA performance in this bandaged body-suit. Don't cross paths with this woman.
Rihanna at a release party for her mo...
Rihanna at a release party for her most recent album, "Rated R". Not looking very celebratory, Rihanna reaffirms this by wearing a spiked minidress made especially for RiRi by The Blonds.
2010: Rihanna's flaming hair matches ...
2010: Rihanna's flaming hair matches the paneled tulle dress from Viktor & Rolf's Spring 2010 collection at the Recording Academy's 2010 GRAMMY Salute To Icons Honoring Clive Davis.
Ruffled and Victorian, Rihanna arrive...
Ruffled and Victorian, Rihanna arrives at the 2010 Grammy's in an Elie Saab Haute Couture piece from the "All White Collection".
Continuing the trend of geometric and...
Continuing the trend of geometric and diaphanous, RiRi arrives at the Echo Award 2010 at Messe Berlin in a bat-cape with shoulder pads. This bodysuit by Alexander Vauthier and pumps by Christian Louboutin is sexy we think, but still utterly confusing.
Rihanna rocks out on American Idol in...
Rihanna rocks out on American Idol in an outfit reminiscent of Michael Jackson's Captain Neo.
Rihanna performs in the Netherlands l...
Rihanna performs in the Netherlands looking a little Gagaesque during her new tour. More power to the flashdance pants and the power-suited shoulders.
Rihanna rejuvenates her style once ag...
Rihanna rejuvenates her style once again, going girly and vivid instead of monochrome and angular. Here she is at TopShop in London with her now iconic red hair in chunky oxfords and a white tutu. It doesn't get more girly than that.
At the 2010 MTV European Music Awards...
At the 2010 MTV European Music Awards, Rihanna trades her spikes for frills in this one-shouldered Marchesa draped tulle gown. The swirling and subtly pink dress is still a strong fashion choice but very feminine.
During MTV's "The Seven" in 2010, Rih...
During MTV's "The Seven" in 2010, Rihanna brings a little Rude Boy back with this vibrant and geometric jacket paired with neon-lined briefs and fire-engine hair.
At the 2010 American Music Awards, Ri...
At the 2010 American Music Awards, Rihanna wears a sheer, lacy Elie Saab Couture gown. The dark scarlet matches perfectly with her curly bob.
At the 2011 Grammy Awards, Rihanna we...
At the 2011 Grammy Awards, Rihanna wears a Jean-Paul Gaultier Couture dress and looks like a sexy Michelin Man or a whipped-cream layered cake.
At the 2011 Brit Awards, Rihanna rock...
At the 2011 Brit Awards, Rihanna rocks a Christian Dior Couture jewel-hued gown. The purple floral bustier paired with the voluminous aqua skirt and adorning bow is youthful and fun.
At Coachella, Rihanna goes full-festi...
At Coachella, Rihanna goes full-festival in an army jacket and cut-off jorts.