Best In Show: 2010
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Kentucky Derby Hat Pageantry1 of 11
Rebecca Romijn, on the arm of a dapper Jerry O'Connell, looks the part of a genteel southern lady in a short white dress and creamy straw hat, decorated with pale blue flowers.
Carousel Cute2 of 11
Sports Illustrated model Marisa Miller knows how to pose in an elegant strapless dress with a petal-embellished skirt and white hat with wide pink band. Mint julep, anyone?
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Shore Blue3 of 11
Real Housewives of New Jersey's Dina Manzo puts the spotlight on a different asset today — her giant, blossoming blue hat. We hope this didn't start any cat fights or table throwing back east.
Drawing Straws4 of 11
Vanessa Minnillo smartly accessorizes her raspberry dress with feminine bow-trimmed sandals, a natural straw hat with yellow and pink blooms, and (of course) boyfriend Nick Lachey.
Bigger & Better5 of 11
Jaime Pressly plays it cool in a one-shoulder periwinkle dress with a chic black hat and heels. She looks quite the dignified opposite of her star turn on My Name Is Earl.
Great Gatsby6 of 11
Awww, Ashlee Simpson-Wentz and husband Pete sweetly coordinated their 1920s-inspired duds. Her ladylike dress, structured bag and heels are topped off with a chic bucket hat. Wonder if they had any awkward run-ins with her former brother-in-law?
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Flip Floppy7 of 11
TV personality Maria Menounos looks pretty darn lucky in a draped coral dress and feather-trimmed floppy hat. No word on whether she had money on Super Saver.
Coming Up Roses8 of 11
Now that's a lovely Derby hat if ever we did see one. We love the soft pink rose blooms on this creation. A very romantic gesture at Churchill Downs.
Witchy Woman9 of 11
In a sea of spring shades, this more macabre take on a racing day topper certainly made us take notice. And we always appreciate anyone unafraid to stand out in the crowd.
Check Mate10 of 11
Frothy, frilly fabric in an overblown gingham print makes this hat look all sorts of light and airy. We're hoping the wind never got a hold of it, because we're certain it would have gotten some serious air.
Petal Pusher11 of 11
Fresh orchids attached to the brim give this floppy red hat a pretty twist. And one that surely smelled amazing — we're betting that those sitting nearby welcomed a natural air freshener at this horsey gathering.