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The 25 Most Outrageous Kentucky Derby Hats Over the Years

I envy the British lasses and southern belles that can throw on a fancy hat without so much as a second thought. Where I'm from, you pretty much can't get away with anything fancier than a baseball cap or beanie without feeling seriously overdressed (or more realistically, like you are just trying way too hard). But there is one occasion where anyone can parade around in a fancy, fabulous, ridiculous or even hideous hat with their head held high; the Kentucky Derby.