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The Most Over-the-Top Hats Spotted at the Kentucky Derby

The Kentucky Derby might technically be all about horse races, but if there's one thing it's really known for, it's this: the giant, over-the-top hats. Since its beginnings in 1875, women have worn their best and flashiest hats to the Kentucky Derby, and, over the years, those hats have gotten increasingly bigger and much more aesthetically adventurous. These days, you're likely to even spot men sporting an over-the-top hat! 

There are a few tried-and-true themes that people have used for their hats at the Derby—horses are an obvious choice, but you'll also see a ton of roses on hats as well. However, some of the best ones are the hats that dare think outside the box and deliver a look that you never expected to see at the Kentucky Derby...or anywhere else, for that matter! There's no shortage of creativity among attendees.  

Today, we're taking a look at some of the most eye-catching, giant hats and headpieces people have ever worn to the Kentucky Derby. There's no denying that the fashion behind many of these is questionable at best, but they are definitely hats that raised some eyebrows and got people talking...for better or worse! 

Let's get started! 

Decked Out From Head to Toe

Decked Out From Head to Toe

This guy decided that an over-the-top hat was simply not enough—he needed a complete over-the-top outfit! And honestly, if this doesn't get people's attention at the Kentucky Derby, there's nothing that will!

As ridiculous as this whole ensemble is, we have to give credit where credit is due: he did a great job dyeing his beard bright red. The color scheme really helps accent his giant horse hat, which is a sentence we never thought we'd ever write! 

Jeffrey Brown/Icon Sportswire/Getty Images

A Colorful Explosion

A Colorful Explosion

This woman (and we're assuming there's actually someone underneath this giant hat) clearly decided to throw everything into this Kentucky Derby hat. Feathers, flowers, lace, and more—all this hat is missing is the kitchen sink. 

The color scheme might look nice on this hat, but it's just way too much of everything. How are you even supposed to watch the races with this giant thing obstructing your sight? Bigger is clearly better at the Kentucky Derby!

Ian Johnson/Icon Sportswire/Getty Images

Keeping Dry

Keeping Dry

This is one thing you normally never see in Kentucky Derby hats: functionality. As ridiculous as this hat looks, this may be the most ingenious person to ever attend this iconic horse race. No one is gonna rain on her parade. 

This might not be your typical Kentucky Derby hat, but it's still one that's very over-the-top. Why solve your rain problem with a boring, old-fashioned umbrella when you can stick it on your head instead? 

Ian Johnson/Icon Sportswire/Getty Images

Disco Derby

Disco Derby

Flowers, feathers, and tons of fabric are all expected when it comes to Kentucky Derby hats. However, one thing you won't see every day is a pair of disco ball cherries! This hat gets an A+ for originality alone. 

There's no denying that this hat is over-the-top, but, we have to admit it's also strangely stylish. It's definitely attention-getting, but it's not nearly as massive or cumbersome as some of the monstrosities you see at the Kentucky Derby. 

Horsephotos/Getty Images Sport/Getty Images

A Big Mess

A Big Mess

When people think of Kentucky Derby hats, they imagine giant, elaborate headpieces. However, this hat proves that bigger is not always better! This is not so much a hat as a fabric explosion. 

We know that you have to suffer for fashion, but we're not sure the neck pain from this giant blob on your head would be worth the "fashion" statement you're making with this hat. Not every hat (or horse) can be a winner at the Kentucky Derby!

Mike Coppola/Getty Images Entertainment/Getty Images

Mile-High Hat

Mile-High Hat

Is this actually a hat or is it some sort of undiscovered sea creature? We would believe either, honestly! We're not sure why the whole "rainbow-colored cloud" look is so popular with Kentucky Derby fans, but you see a ton of these ridiculous hats there. 

We'd love to know how many people this woman accidentally bumped into because this humongous hat impeded her vision. Honestly, we imagine that the whole Kentucky Derby is just people in ridiculous, large hats running into one another! 

Logan Riely/Getty Images Sport/Getty Images

His Thoughts Are Racing

His Thoughts Are Racing

This guy proves that it's not just ladies who enjoy crazy hats at the Kentucky Derby. Who needs to watch the races when you've got your own derby right on your head? 

This gentleman probably didn't need to go so literal with his theme, but it's clear that he probably made this entire thing himself. As long as you've got on an over-the-top hat, you're welcome at the Kentucky Derby. 

Mike Coppola/Getty Images Entertainment/Getty Images

A Deadly Hat

A Deadly Hat

You should always expect the unexpected when it comes to Kentucky Derby hats, but we never thought we'd see one with a flamingo skeleton theme! This hat is beautifully made, but it's just so weird. 

What really pushes this one to greatness is the fact that the flamingo on her hat has his own hat with a flamingo on it. Two is better than one when it comes to Kentucky Derby hats! 

Mike Coppola/Getty Images Entertainment/Getty Images

A Religious Experience

A Religious Experience

When it comes to the crazy hats you see at the Kentucky Derby, it's best to not ask questions and just go with it. And that goes double for this Pope-inspired pink getup! There's no explaining what's going on. 

While the ridiculous hat might be the main event, we have to admit that it's the pink sunglasses that really bring this whole ensemble together. The devil may be in the details, but the Lord is in this hat! 

Ronald C. Modra/Getty Images Sport/Getty Images

Keeping Things Simple

Keeping Things Simple

A good Kentucky Derby hat doesn't have to be overly elaborate. Sometimes it pays to return to the basics and just throw a horse head on top of yours. It's over-the-top and it fits the theme—what's not to love? 

If this guy plays his cards right, he might be able to sneak onto the track and run a race himself. Nobody will even notice because they're all to busy checking out all the crazy hats! 

Jim Owens/Icon Sportswire/Getty Images

Flower Power

Flower Power

Roses are a common theme for Kentucky Derby hats, and it's clear that this guy has taken his love for the flowers to the extreme. Maybe he was actually headed for a gardening expo but got a little turned around. 

If those were real flowers, he could probably support a colony of bees from his hat alone. Let's just hope that he never turns that into an idea for a new hat! 

Rob Carr/Getty Images Sport/Getty Images

With a Bow on Top

With a Bow on Top

Is this an over-the-top Kentucky Derby hat or is this cheating? It's not so much a hat as it is a giant bow! We really need the Kentucky Derby experts to weigh in on this one. 

This is not the worst look in the world, and the giant bow is definitely giving us Sia vibes. But, compared to some of the crazy things you see at the Derby, this one is pretty tame by comparison. 

Harry How/Getty Images Sport/Getty Images

Derby Talk

Derby Talk

This woman is killing two birds with one stone. She's going to wear this hat to the Kentucky Derby and then pop on down to New Orleans to celebrate Mardi Gras in it as well! It's truly a hat for every occasion. 

Seeing someone wear this giant hat raises an important question—do all these crazy hats hurt to wear? Is she going to have to pop by for a visit to the chiropractor after the races are over? 

Al Bello/Getty Images Sport/Getty Images

Derby Bros

Derby Bros

These guys prove that the Kentucky Derby is much more fun when you have friends to wear stupid hats with you. We're honestly not sure who's the most over-the-top out of these three! 

We know nothing about who these guys are, but I'm willing to bet that alcohol factored heavily into the creation and wearing of these hats. And there's no better place to be tipsy and ridiculous than the Kentucky Derby! 

Jamie Squire/Getty Images Sport/Getty Images

The Final Boss of Derby Hats

The Final Boss of Derby Hats

Is this guy wearing a hat or is he being abducted by aliens who are also big fans of the Kentucky Derby? Either way, this is definitely one of the most bombastic displays you'll ever see at the races. 

While this guy might have to worry about not toppling over, he'll never have to worry about the weather at the Kentucky Derby! If you ask nicely, he might even let you huddle under there too. 

Jamie Squire/Getty Images Sport/Getty Images