I mean, “best” is a tough word to define. What makes a good Kentucky Derby hat? Is it just big-ness? Or are there more points to be gained in feathers, bright colors, or avant garde style? Well, we’ve got some of our favorites that you can judge for yourself, after the jump! 


You can’t help but smile (maybe even laugh a little) at these garish chapeaus. It’s a tradition ladies (and gents!) in attendance don’t take lightly, as many of these hats are custom made and likely cost a pretty penny. They might be silly, but they’re sure fun to look at! Take a look at some of the best in the gallery and tell us:

Which hat is your favorite?

[source, source]