5. Sandra Bullock
We’re not really sure what the 51-year-old was thinking when she chose this sloppy ensemble for the 2005 Teen Choice Awards. Bullock’s outfit look confused, featuring flared jeans, a biker tee, black blazer and strappy sandals. The Gravity star’s style has thankfully improved over the years. Sandra looks sleek and sophisticated at the 2014 Palm Springs International Film Festival Awards gala in this two-toned look.
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