Take a look at what Hayden Panettiere, Heidi Klum, January Jones and others wore
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Bad: Lena Dunham
This might be a lovely illustration for a book titled, "How to Look Dumpier, Chubbier and Older Than You Really Are." If this is one of those "look at how I recycled my ugliest bridesmaid dress" challenges, she may win the bet but really, I don't think appearing in this hellaciously ugly thing is worth any amount of money, much less bragging rights.