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18. Sophisticated Songstress

Miley wore a striking asymmetrical Herve Leger by Max Azria gown to the Grammy Awards in February of 2009. Although the dress was form-fitting, it wasn't too revealing and the flower detail on the shoulder added a young girlish vibe. Miley, of course, added her signature stacked bracelets and she finished off the look with a large pair of diamond drop earrings by Mimi So.