2004: Anna Nicole Smith got into the Kentucky Derby spirit wearing a pink
ribbon hat and matching gloves, which her pal Bobby Trendy most likely
designed for her.

2006: Jaime Pressly was a polka dot princess at the Derby, wearing a floppy
hat with a sexy bustier dress.

2008: Kendra Wilkinson, Bridget Marquardt and Holly Madison joined Hugh
Hefner, rocking sexy Derby attire!

2008: Adrian Grenier and Isabel Lucas looked Kentucky Derby divine!

2009: Wearing a floral frock with a red ribboned hat and matching heels,
Leann Rimes was Derby delightful!

2009: Bethenny Frankel definitely stood out in her Derby duds! The Real
Housewife rocked a fun floppy hat with a bell-bottom jumpsuit.

2009: Brooke Shields was a Derby fascinator, wearing a veiled royal blue
hat.

2010: Mario Lopez showed off Courtney Laine Mazza’s baby bump at the Derby
last year.

2010: Ashlee Simpson and Pete Wentz took a blast to the past at last year’s
Derby, rocking 1930’s style threads.

2010: Rebecca Romijn and Jerry O’Connell never miss a chance to be the best
dressed duo! The supermodel-turned-actress and her hunky hubby were dressed
to impress at the Kentucky Derby last year.