The 21 Sassiest Hats at the Kentucky Derby

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By Christine Erickson2014-05-03 13:15:59 UTC

Friday marked the 140th annual Kentucky Derby, a two-day horse racing event filled with gambling, mint juleps and the largest hats you could possibly imagine.

The derby started in the 1870s as a regal affair, in which women dressed to the nines with matching accessories. As women's fashion got louder in the '60s, the hats at the event became the over-the-top, signature accessory known today.

It's considered good luck to wear a hat to the Kentucky Derby, but it has more-so become a tradition that simply allows women and men to dress up. Like a giant, themed tailgate party, with the potential to win money.

That doesn't mean we're not baffled at how these ladies manage to walk around without falling over. Take a look at some of this year's most elaborate hats.