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 Wedges

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

Ashlee Simpson Cloche

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