Hat

"I can wear a hat or take it off, but either way it's a conversation piece."

... Hedda Hopper

Beret

Derek K

Source

Hats On Derby Day

Kerry Degman (who I recently RAN INTO)

"Wearing a fashionable (if not gaudy) hat to the Kentucky Derby is one of the most notable traditions associated with the fabled race. Just about everyone you run into at Churchill Downs on race-day will be wearing a lavishly designed or creatively pieced-together hat.

Generally, you'll see classy and fashionable hats in the Clubhouse and Paddock areas, but the infield seating hosts an open-season for mad hatters and meticulous milliners alike to display their creative flare for headwear." (Source)

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Mad Hatters