VOTE The Weirdest Kentucky Derby Hats Ever Caught on Camera  

Ashley Reign
1.2k votes 149 voters 25.8k views 33 items Embed

List Rules Vote for the most outrageous derby hats ever caught on film

Though almost everyone in America has heard of the Kentucky Derby, there are many among us who have never been blessed with a true understanding of the outlandish fashions that are shamelessly paraded throughout the event each year. Well, get ready to get educated as you behold this collection of the most outrageous Kentucky Derby hats ever! 

 

As you’re introduced below to some of the most… “creative” hats ever caught on film, you may catch yourself alternating between the instinct to rejoice in the madness and the nagging need to understand how such a fashion phenomenon could’ve ever happened. Rest assured this is normal and allow us to explain.

 

The legend of the Kentucky Derby hat goes all the way back to the 1870’s and the founder of the Kentucky Derby himself, a gentleman named Colonial Meriwether Lewis Clark Jr. Now back in Junior’s day,the racetrack held about as much appeal to women and the elite as dinner at a run-down Taco Bell in the sketchiest part of town. But, as you might suspect, a guy with a name like Meriwether had spent a lifetime learning to look on the bright side.

 

With his wife’s help, the Colonial waged a campaign to convince the Louisville, KY elite that the Derby was the hottest place to see and be seen in all the latest fashions- and it actually worked. As media evolved and became increasingly widespread over the years, the women of the Kentucky Derby got bolder and bolder in order to stand out in the crowd. As you’ll see below, their boldness eventually exploded into the outlandish fashion fest it is today. So without further ado, we give you some of the most outrageous Kentucky Derby hats ever.

1
38 13

The "Something Just Ain't Right About That" Hat


The "Something Just Ain... is listed (or ranked) 1 on the list The Weirdest Kentucky Derby Hats Ever Caught on Camera
Photo: via Imgur
2
39 18

The "Actually Pretty Pimp Despite Itself" Hat


The "Actually Pretty Pimp ... is listed (or ranked) 2 on the list The Weirdest Kentucky Derby Hats Ever Caught on Camera
Photo: via Wikimedia
3
36 16

The "Georgia O'Keefe Exploded On My Head" Hat


The "Georgia O'Keefe E... is listed (or ranked) 3 on the list The Weirdest Kentucky Derby Hats Ever Caught on Camera
Photo: via Pinterest
4
31 17

The "I Totally Traded My Hat For The Drink That Came In This" Hat


The "I Totally Traded My H... is listed (or ranked) 4 on the list The Weirdest Kentucky Derby Hats Ever Caught on Camera
Photo: via Twitter