40 of the Most Outrageous Kentucky Derby Hats of All Time
These people aren't horsing around!
Every year since 1875, the Kentucky Derby has taken place on the first Saturday in May, with two exceptions. The race was postponed in 1945 due to World War II — and things will look a little different this year as well. Because of the novel coronavirus pandemic, the 146th Kentucky Derby has been pushed back to September 5, 2020. So while we all hold our horses until the fall, we're looking back at the most outrageous, over-the-top Derby hats that we could find from past races, worn by the Derby's boldest race-goers.
From papier-mâché horses to a garden's worth of flowers, these caps are nothing if not creative. While some like to keep it simple with a mini fascinator, others embrace the tradition of larger-than-life hats — and the race simply would not be the same without them. So grab your mint julep (or your mint julep cupcakes!) and get excited for the most exciting two minutes in sports with these wild and wacky Kentucky Derby hats — because we all know that the hats are the best part of the experience.
The Mad Hatter
No, that's not a character from Alice and Wonderland — but we have a guess as to where this party goer got her hat inspo for the 2019 Kentucky Derby.
Hair or Hat?
Another stand out from last year's derby is this daring look. Part bun, part hat and paired with leopard print this is certainly wild.
Everything's Coming Up Roses
A simple hat of roses wasn't enough for this 2019 Kentucky Derby-goer, hence the three balls of roses hanging off the sides.
Power Couple
Now that's what I like to call horse power! These two Derby goers put their heads together at the 145th running of the Kentucky Derby.
Less-Than-Mellow Yellow
Yellow rose? Check. Yellow veil? Check. Animal-print hat? Check. This hat from the 2018 Derby was a bright and sunny standout.
Rain or Shine Hat
A little rain didn't spoil the fun for this 2018 Kentucky Derby attendee.
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Butterfly Fascinator
Butterflies in your stomach? Not the case for this 2017 watcher of the Kentucky Derby.
Horsing Around
Not into the classic fedora look? No harm no foal. Take cue from this gent who may or may not have stolen this look from his son's toy room for the 2017 Kentucky Derby day.
Flower Power
This woman proves that there's no such thing as a hat that's too big at the 2017 event.
Mardi Gras Meets Derby
Turn your junk drawer into a masterpiece like this woman did in 2017. She created a spunky hat out of a crown, feathers, Derby-inspired toys, and so much more.
Run for the Roses
Roses aren't the only thing that are red at the Derby. This festive Derby guest at the 2017 Kentucky Derby dyed his beard red to show off his pride.
Plaid Pony
You're never to old to bring your stuffed animal along! This man rocked a plaid hat in 2017 with a cheeky stuffed horse wrapped around it.
Disco Cherry
Life is just a bowl of cherries! This fun and fruity headpiece was one of the most over-the-top hats at the 2016 race.
Steel Magnolia
This guest was spotted at Bravo star Kim Zolciak's 2016 Kentucky Derby hat contest at the Empire City Casino in Yonkers, NY, but we'll let it slide that she wasn't actually at Churchill Downs because her giant flower is to die for!
Hog Heaven
Maybe she's a Peppa Pig fan?
Rose Garden
One rose wasn't enough for this attendee — she brought the whole garden!
Bird's Eye View
This wise Derby fan opted for an extra set of eyes on the prize at the 142nd Kentucky Derby at Churchill Downs.
Off to the Races
This 2016 race fan knew he had a cheeky hat straight out of the gate!
Cotton Candy Topper
Where not sure if there is even a hat under this cloud of cotton-candy-colored tulle worn at the 2016 race, but when it comes to the Derby, anything goes!
Prize Winner
This attendee shows off her Derby pride at the 141st Kentucky Derby in 2015 with an award ribbon-adorned hat.
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