Rihanna: The Road to the Red Carpet

From ball gowns to bra tops, W’s September cover star Rihanna has worn it all. See her best looks here.

Rihanna in Chanel in 2009

In 2005, Rihanna’s wardrobe consisted of a steady supply of crop tops and slouchy jeans. But even then the star knew that adding little touches like paint splatters and printed sneakers—art school chic, anyone?—was, at the very least, interesting.

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Up with the glam and down with the hair, Rihanna stunned in a backless white mini dress by Zac Posen at the 2006 Billboard Music Awards. Red lips, red nails, and sleek gold sandals kept things cool and classic.

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Sleek, chic, and covered in gems at the 2009 Chanel show—tweed has never looked so angsty.

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The pop star upped the drama for a 2010 appearance, in a cut-up Viktor & Rolf dress and a golden blonde bouffant. Pastel eye shadow and nude pumps were safe choices, but suited the sugary sweet look nonetheless.

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Rihanna’s red period was full of memorable moments, but none could top this coordinated Elie Saab look at the 2010 AMAs.

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The star took the men’s wear trend to a whole new level in 2012 by wearing—wait for it—actual men’s wear from Acne and Raf Simons. Pin-up girl hair and makeup provided a nice counter-balance.

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With a slinky, down-to-there dress by Giorgio Armani, Jacquie Aiche and Neil Lane jewels, a curly blonde bob, and glowing skin, Rihanna was untouchable at the 2012 Grammys.

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The star did her best Cher Horowitz impression at the 2012 GQ Men of the Year Awards in a red Calvin Klein slip dress and Manolo Blahnik heels.

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Rihanna seamlessly mixed old-school glamour with lotsa skin in a black two-piece gown by Jean Paul Gaultier at the 2013 American Music Awards.

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Rihanna picked up the Fashion Icon award at the 2014 CFDAs in a Swarovski-covered custom Adam Selman gown, matching turban, and baby pink fur throw. This outfit won’t be forgotten anytime soon.

Photo by Sherly Rabbani