Kentucky Derby: A World Where Men Place Bets and Women Wear Large Hats

May 3, 2010 • Magazine

While Wikipedia calls the Kentucky Derby a "Grade 1 stakes race for three-year old Thoroughbred horses, held annually in Louisville, Kentucky", for me, the Kentucky Derby means high society debutantes placing horse bets and women wearing large hats. 

The Kentucky Derby is one of the USA's oldest Thoroughbred horse races with lots of history under its belt, and so when I heard about this year's affair, I figured the fashion, would add to its authenticity and historical value. 

Not sure why I felt this way, but I was pretty much wrong. Aside from those floral centerpieces and large straw hats, I felt that many of the women dressed stylishly, yet immodestly and not at all in the vision of what I have come to believe is the Kentucky Derby. (Hey, it's only my opinion.)

Then again, it is the 21st century.  There were a few stylish surprises that got me grinning.

Cutest Couple

Ashlee Simpson-Wentz and Pete Wentz

Mod Couple

Rebecca Romijn and Jerry O'Connell

Worst Dressed Couple

Nick Lachey & Vanessa Minillo

Little Bo Peep

Marisa Miller

Fire Engine Red

Maria Menounos

Ultimately Predictable: The Nanny–With A Hat

Fran Drescher

Little Cindy Brady Doesn't Grow Up

Jennifer Elise Cox

Urban Take on an Old World Hat

Linda Cardellini

Photos: Wireimage

–Simona Kogan

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