Gallery: CFDA Style Icon Rihanna's Best Looks

Rihanna’s reputation as a high-fashion aficionado has finally been acknowledged by the chief rank: she’ll be awarded the prestigious title of CFDA Fashion Icon at the CFDA Fashion Awards in New York on Monday, June 2. (Watch them here on June 3.)

Riri is in stylish company, joining previous winners Kate Moss, Iman and Sarah Jessica Parker. Here at FLARE, we’ve been crushing on her style for years. Thus, we present a look back at RiRi’s most memorable off-duty looks—from fresh-faced teen to full-fledged fashion icon. —Kaitlyn McInnis

Rihanna: 18 Looks That Confirm RiRi is Our Generation’s Fashion Icon

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2005 Back when our Barbadian beauty was fresh on the scene, she was spotted in flared denim with just the right amount of lace undies peeking out.