The craziest hats of the Kentucky Derby

The Kentucky Derby, known as the fastest two minutes in sports, is the culmination of the hard work of thousands of horses, owners, trainers and jockeys. Only twenty horses will vie for the coveted title, after multiple preliminary races to determine the best of the best.

Between "Prep Season" races and a "Championship Series" leading up to the big day, 2013 was the first year in which the top four finishing horses for each race receive a certain number of points. At the end of the season, all of these points will be tallied to see which 20 will enter the Derby. Previously the determination was made using grade stakes earnings.

The Craziest Hats at the Kentucky Derby
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The Craziest Hats at the Kentucky Derby
This hat is pretty silly, but also very simple: only one flower needed!
This woman clearly wanted to be taller, choosing such a slim, sky-reaching hat.
These two gents, Charles Matasich and George Holter, wearing two of the most photographed hats at the Kentucky Derby.
This intricate hat won't do much to protect this woman's skin or eyes from the sun, but at least it makes a statement.
Wearing a pink suit wasn't enough for fan Alice Ginart when it comes to standing out, she amps it up with a bright feathered hat!
This fan, Tony Offutt, had to have a sore neck by the end of the day...
Anna Nicole Smith attends the Derby in a baby pink, volume-ridden hat.
Jessica Simpson wears a colorful hat during Kentucky Derby day festivities in 2004.
Fan Jim LaRochelle wore a smiling box hat, and kissed by Susan Helms, of Chicago, during the Kentucky Derby. Judging by all the lipstick, we think this guy had the right idea.
Is there someone under there? Between the vibrant feathers and camera, her hand is the only thing telling us someone is wearing this hat.
A cowboy hat gone wrong, with far too many feathers!
Victoria Gotti matched her hat to her hair and outfit at the 2005 Kentucky Derby.
These three men are clearly a lot of fun, and we're just dying to know if they made these hats themselves... and how long it took!
This man makes a statement with his hat, asking to "Bring R Soldiers Home," and he certainly has all eyes on him with how tall it is!
Intricate and delicate, we hope this woman treats her hat gingerly.

A sheer hat won't provide too much protection for Lee Ann Womack, but we know, it's all about how you look.

Of course, Kim Kardashian attends the Derby too! A slightly milder hat, but fun all the same.
This woman probably wins the award for largest hat... um, ever.
Barack and Michelle, is that you? This woman put the President and First Lady's photos on faces of these two fake jockeys!
Now that's dedication.  These two ladies don't want to get their hats or outfits wet, but still won't miss the race!
Is L.A. Lakers Scout Bonnie-Jill Laflin channeling the actual horses at the race?
This fan looks extremely proud of his headgear.
Between this fan's red hair and the vibrant green of her hat, we're sensing a St. Patrick's Day vibe!
Wait, wrong event.  This fan adds some flowers to the cheese head hat for the derby, obviously supporting her football team in a subtle way!
Star Jones has layers and layers of feathers on her hat, which are clearly weighing down the left side.
It's 2012, and we're not surprised to see this inventive neon hat!
Another fan reaching for the sky! If he was looking for attention, he certainly got it.

While it has always been a huge event in the world of horse racing, the Kentucky Derby has also become quite the event in the world of style. People flock to Churchill Downs, KY every year, eager to watch the horse race, and some perhaps even more eager to show off their creativity.

In its beginnings in 1875, wearing a hat to an outdoor event was seen as a necessity for both men and women. Well-to-do ladies of the time saw this event as an opportunity to be seen in the latest fashions, and had access to many talented Louisville seamstresses. As the race takes place in the Spring, many women wore silk, and hats helped to shield them from the sun.

Through the years, the fashion for the event has evolved just as rapidly as it did on the runway, but a few things remained. Women dressed in their best, and always topped off the look with a fabulous hat. And why wouldn't they? For the Derby, it is believed to bring good luck! As the event steadily gained popularity, women started to have more fun with their accessories. Society may have loosened the reins (ha - yes, pun intended) on the necessity to wear a hat and gloves wherever a woman went, but the Derby provided a place for the nostalgic to continue this trend, and in a fun way.

There are no rules when it comes to head accessories, and many are seen in classy, fashionable looks, while others sport crazier inventions. Take a look through the gallery above to see some of the funniest and coolest hats of the Kentucky Derby!

Photo Credit: AP; Getty Images

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