Pete Wentz and Ashlee Simpson-Wentz attend the 136th Kentucky Derby on May 1, 2010 in Louisville, Kentucky.
(April 30, 2010 - Source: Jeff Gentner/Getty Images North America) see more angles »

Ashlee Simpson Cloche

The singer looked ladylike in an ivory dress hat with floral detailing.

Ashlee Simpson Wedges

Ashlee looked polished from head to toe in an orange and ivory ensemble completed by a pair of two-toned, ankle strap wedges.
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