Singer Ashlee Simpson arrives at the Conde Nast Traveler 8th Annual Hot List party at Mansion on April 17, 2008 in New York City.
(April 17, 2008 - Source: Bryan Bedder/Getty Images North America) see more angles »
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Ashlee Simpson Messy Updo

Ashlee does a great job at adding her own flavor to a simple ensemble. Her piecey hot red updo was the perfect way to complete this look with her own signature style.