Wackiest Hats at the Kentucky Derby Horse Races

Since 1875, sophisticates have attended the Kentucky Derby in Louisville, Kentucky, to sip mint juleps, cheer on their favorite racehorses and, oh, who we are kidding? The Kentucky Derby is all about the hats.

The Derby hats tradition dates back to the beginning of the horse race, when founder Col. Meriwether Lewis Clark Jr. recruited high-society women to wear their finest headpieces to the event. It was an effort to restyle the racetrack into a place of class instead of boozy illegality.

Over the years, more people — both women and men — began going bigger and, well, weirder with their horse-race hat choices, leading to some truly imaginative creations. From a crown of straws to a stuffed-animal tableau to a bird-adorned pinwheel, these hats are next-level wacky. And next-level fabulous.

Hold Your Horses

This spectator abides by that old adage: Keep your friends close and your mannequin heads closer.

From the 142nd running of the Kentucky Derby horse race at Churchill Downs on May 7, 2016, in Louisville. 

Clowning Around

The next time a clown comes to your child's birthday party, ask them to make you a horse-themed balloon hat — so your Derby hat can be as cool as this.

From the 137th Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2011, in Louisville. 

The Final Straws

Ironically, the wearer of this hat is not using a straw for her drink.

From the 137th Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2011, in Louisville. 

Thrown Together

Now that's how you make an entrance.

From the infield before the 142nd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2016, in Louisville. 

Go Big or Go Home

Tammy Behr, from Louisville, Ky., knows the golden ratio for Derby headpieces is 90% flower, 10% hat.

From the 139th Kentucky Oaks at Churchill Downs Friday, May 3, 2013, in Louisville. 

Go Bigger or Go Home

Actually, why not just make the entire hat a flower? Even better!

From the 143rd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 6, 2017, in Louisville. 

Hatwoman

We will definitely be buying tickets to this superhero flick.

From the 142nd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2016, in Louisville. 

Spicy!

That's hot. Literally.

Fans celebrate the 2017 Kentucky Derby. 

Upside Down

Pseudo-celebrities Jax Taylor and Brittany Cartwright — of reality TV juggernaut Vanderpump Rules — walk the Kentucky Derby red carpet. Who wants to tell Brittany her hat isn't on the right way?

From Churchill Downs in Louisville on Saturday, May 6, 2017.

Bottoms Up!

Olympian Johnny Weir loses his cocktail...in his hat.

From the 2015 Kentucky Derby on Saturday, May 2, 2015 at Churchill Downs in Louisville. 

Merry Go Round

B+ for the pretty rose-lined hat. A+++ for the nature helmet festooned with a horce-racing tableau. 

View from the Top

This man takes derby racing as seriously as he takes hats. Which is to say, very. 

From the 142nd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2016, in Louisville. 

Red, White, and Whew

Because nothing says "Derby" like "patriotic peacock." 

From the 143rd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 6, 2017, in Louisville. 

Birds of a Feather

Andrea Godlew combines two hallmarks of hat wackiness — flowers and bird feathers — for a double whammy of fun.

From the 142nd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2016, in Louisville. 

Rain or Shine

Think a little rain can stop a lady from getting her Derby hat on? Never! Jennifer Parod, Tucson, Az., covers her headpiece with a demure plastic bag.

From the 139th Kentucky Derby at Churchill Downs Saturday, May 4, 2013, in Louisville. 

Invincible Spirit

Barbaro, winner of the 2006 Derby, gets his due .

From Churchill Downs in Louisville, Saturday, May 5, 2007. 

Big Red

Known fact: The best Derby hats are roughly the same size as their wearer. Patty Ethington of Shelbyville, Ky., shows how it's done.

From the 135th Kentucky Derby at Churchill Downs Saturday, May 2, 2009, in Louisville. 

Derby Pride

Is this a hat, or a live shot from the track? It's honestly hard to say. Erica Harris of Omaha, Neb., is the true winner of this Derby.

From the 136th Kentucky Derby at Churchill Downs Saturday, May 1, 2010, in Louisville. 

Top Four

Why is the fourth-place horse missing a leg? One of the many mysteries of this hat.

From the 141st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 2, 2015, in Louisville. 

Will You Accept This Rose?

This horse seems to be taking his cues from "The Bachelor." As he should.

From the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville.

 

=Flamin-Go Get 'Em

The only way this hat could be better is if the flamingo were real.

Gold (pink?) star for this custom made hat seen at the 145th Kentucky Derby race at Churchill Downs in 2019. 

Pretty in Pom Poms

Another fabulous find at the 2019 Kentucky Derby, this one has it all: feathers, pom poms, ribbon and rhinestones. 

Even the Dog Has a Kentucky Derby Hat

When Star Jones attended the G.H. Mumm Champagne event at the 2016 Kentucky Derby, she delivered two stellar hat performances: her own and that of her precious pup.

Her hat looks almost like a real lily flower, while her Maltese's is a regal crown.

Birds of a Feather Flock Together

Every year, the Derby Princesses appear in matching outfits. Needless to say, themed hats are an essential component.

These mint green and pale pink hats were spotted at the 2015 Kentucky Derby.

...Or Explode?

If over the top is the point, this woman at the 2019 Kentucky Derby wins, hands down.

A Covid Hat. How Festive.

When a catastrophic pandemic interferes with your plans, you can run from it, or you can embrace it.

This man at the 2021 Kentucky Derby chose the latter. 

Show Your Spirit

The Kentucky Derby is an American event if ever we saw one. Patriotism, as displayed in the above photo from the 2019 Kentucky Derby, is more than welcome.

Alternatively, Morph Into Uncle Sam

If standard-issue American spirit doesn't quite do it, you can always follow the lead of the man who wore this authentic Uncle Sam outfit to the 2016 Kentucky Derby.

His shades don't fit the look, but we'll let it slide. UV damage is no joke.

Tiz the Law

We can tell who this woman was rooting for. Her hat features Tiz the Law, an American thoroughbred who won the 2020 Belmont Stakes, Travers Stakes and Florida Derby.

At the 2020 Kentucky Derby, the year this encouraging hat was worn, Tiz the Law ended up placing second.

Shine Bright Like a Diamond

More like a lemon, actually. This woman at the 2019 Kentucky Derby made the bold move to leave traditional pastel shades behind, and we're loving it. 

The Bigger, the Better

Another fun hat spotted at the 2019 Kentucky Derby featured a brim with dangling, white pompoms, plus bold flowers and feathers that matched the wearer's striped dress perfectly.

Go the Extra Mile

If you're crafty enough to wear the entire race on your head, like this man at the 2016 Kentucky Derby, go for it. 

Sound the Horns

The Kentucky Derby might be a solidly American event, but everyone is welcome to partake in the festivities.

Randy Kvasic from Croatia is pictured above in the hat he designed for the 2018 Kentucky Derby.

Whirligig Hats Are Back

Some hats are elegant. Some are unique.

We'll let you guess which category this hat from the 2018 Kentucky Derby falls under.    

Looks Like a School Project

Personally, we think this hat could have some more flair. The ribbons are tiny, and the plastic horse figurines are underwhelming.

Patrice Rodden of West Islip, New York wore this to show her support for her favorite horse in 2015. A for effort, B- for execution.