August 31, 2006 - Peter Kramer/Getty Images Entertainment more pics like this »
8. Rihanna 2006
Attending her second VMAs in 2006, Rihanna opted for a flirty white mini dress with spaghetti straps and silver beading around the waist and hem. She was only 18 then and this was exactly what one would expect from a teenage pop star.

RiRi teamed her frock with bejeweled gray slingbacks and sparkling jewels that included a link bracelet, a chunky ring, and a pair of dangling earrings. She topped off her look with a loose feathered hairstyle, smoky eyes, and a natural lip.