(September 22, 2008 - Source: Stephen Shugerman/Getty Images North America) more pics like this »
6. 2008

The teen queen attempted to show off this ill-fitting fluffy black dress at a September 2008 party. The shapeless dress made the petite star look bigger than she is, which was hard to do considering the dress was black. Her loose ponytail and subtle pink lips give the ensemble a fresh young look, however. Also, her shoes looked very familiar considering she wore the exact same pair to the opening of Mamma Mia a few months prior.
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