BOOGIE WOOGIE
The singer channels 1940s glamour by pairing glossy pink lips and long black lashes with a retro red hat on a chilly day in the U.K.
SCREEN SIREN
The "Umbrella" singer goes for Old Hollywood glam at the 2007 World Music Awards with dramatic cat-eye liner and ruby lips that perfectly compliment her emerald-hued Dolce & Gabbana gown.
CHARITY CASE
The Armani-clad performer pairs a sleek peek-a-boo bob with nude lips and mossy green eyeshadow for a UNICEF benefit in October.
COVER UP
Earlier that day, the singer is more downtown cool in her grey beanie, sparkling shadow and glossy lips at TRL – which she co-hosted with rumoured fling Josh Hartnett.
TAKE A BOW
The jet-setting Barbados native looks relaxed and elegant with a sleek side-swept bob and shimmering smoky eyes backstage before a London performance.
DOO WOP
Soft curls, strong black liner and pale pink lips lend a '60s girl-group feel when the singer visits the PEOPLE Music Lounge in N.Y.C.
JAGGED EDGE
Rihanna contrasts a punky, piece-y bob with heavy smoky eyes and shimmering copper gloss in Tokyo for the Live Earth concert.
PAPER DOLL
Just a few days later the ever-changing singer lets her hair down into long curls with soft rose lips and eyes at a party celebrating her Paper cover.
FLAPPER GIRL
A sharp bob with blunt bangs and bold violet lips give the singer, in Zac Posen, a sophisticated 1920's look for the MTV Movie Awards.
OFF CENTRE
The Gucci-clad singer shows off her fun side at Nickelodeon’s 20th Annual Kid’s Choice Awards in a trendsetting asymmetrical bob and purple eyes.
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