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The 21 Goofiest Hats At The 2012 Kentucky Derby

by: Esteban On  Monday, May 7, 2012

2012 kentucky derby crazy hats

Every year on the first Saturday of May, millions of people who otherwise have no interest in horse racing suddenly become captivated by so-called “most exciting two minutes in sports”—the Kentucky Derby. This past Saturday’s event, won by I’ll Have Another, was the 138th “Run for the Roses,” and it was certainly huge pop culture event.

So what’s the big deal about the Kentucky Derby?

Well, some would say that people are enamored with all the history and pageantry of Churchill Downs. And this is probably true. A lot of people probably do love the romance and charm of the Kentucky Derby, with its seersucker suits and straw hats. But personally, I think the main answer is actually a little simpler than that. I think most people just love an excuse to drink in the afternoon and wear silly hats. In this sense, the Kentucky Derby is really just St. Patrick’s Day with jockeys and mint juleps instead of leprechauns and Guinness.

Today, in honor of the most famous horse race in the world (or so we assume here in North America), let’s take a look at the goofiest hats spotted over the weekend in Louisville, Kentucky. Some are trying to be classy; others are just trying to be seen. But regardless, they’re all pretty hilarious.

21. A hat on a hat

#21 crazy white hat with blue feathers 2012 kentucky derby

Can’t decide between two hats? Just have your hat guy hot glue one to the other and—boom—super awesome megahat.

20. Christmas in May

#20 stupid 2012 kentucky derby hat dude

Hey, who knew the Ghost of Christmas Present was a fan of horse racing?

19. The Black Widow 2012

2012 kentucky derby crazy hat

Is it just me, or does this hat seem a little dark and serious for a fun, lighthearted event like the Kentucky Derby?

18. Three Amigos

#18 crazy weird funny stupid 2012 kentucky derby hats cinco de derby sombreros

This year the Derby fell on May 5, so of course you knew there would be a number of Cinco de Mayo-themed hats. (Like I said, people love any excuse to wear silly hats and drink in the afternoon.)

17. Macaroni

#17 blue feather goofy kentucky derby 2012 hat

This Yankee Doodle may not be riding on a pony, but her money is. So yeah, we’ll call this hat macaroni.

16. Stripes

#16 crazy 2012 kentucky derby striped top hat and suit

This hat would still be pretty great without the matching suit. But the suit helps.

15. UFO Hat, Part I

#15 cyndi lauper huge red hat kentucky derby 2012

Cyndi Lauper shows up to Churchill Downs in a hat that doubles as an umbrella.

14. UFO Hat, Part II

#14 red UFO hat 2012 kentucky derby (miss america laura kaeppeler)

This is Laura Kaeppeler, the reigning Miss America. Her hat looks like Cyndi Lauper’s after the wind has blown it inside out.

13. Star Jones' Blue Mess

star jones 2012 kentucky derby stupid hat

The hat sported by this former host of The View features one of the busiest arrangements of plumage at this year’s Derby. Obviously, it’s not really working for her.

12. Black poppy

#12 crazy weird funny stupid 2012 kentucky derby hats

Is this a hat, or an oversized hair clip? (Yes, I realize there’s probably a name for this type of headgear. I’m not going to look it up because I don’t want that information taking up space in my brain.)

11. The Fluffy Hat

#11 crazy weird funny stupid 2012 kentucky derby hats - feather hat woman making stupid face

I bet this woman was just delighted when she discovered that this photo of her was all over the internet on Sunday. You know, because it’s so flattering and whatnot.

10. The Rose Top Hat Guy

#10 crazy weird funny stupid 2012 kentucky derby hats rose hat guy

You want to know the crazy thing about this guy? He apparently wears this hat to the Kentucky Derby every year. There are numerous photos of him wearing this hat, but with different clothes. I guess he figures why mess with success.

9. Sombrero Delux

#9 crazy weird funny stupid 2012 kentucky derby hats sombreros

I like how the guys up at #18 have horses racing around their sombreros, but this guy has horses dangling from his sombrero, plus a miniature Churchill Downs steeple and some wacky horse show sunglasses. So in other words, he took the Cinco de Mayo them up a notch.

8. Scary bird hat

#8 crazy weird funny stupid 2012 kentucky derby hats scary feather hat

I wonder if any exotic birds swooped down and tried to get busy with this lady’s head.

7. The Chihuly

#7 crazy weird funny stupid 2012 kentucky derby hats abstract art hat

Ever been to the Bellagio in Las Vegas and seen the huge glass sculpture ceiling by Dale Chihuly? That’s what this reminds me of.

6. The Bushy Peacock

#6 crazy weird funny stupid 2012 kentucky derby hats huge feather hat

How many poor innocent peacocks lost their beautiful feathers so this lady could wear this ridiculous hat to the Kentucky Derby?

5. Gigantic cartoon hat

#5 crazy weird funny stupid 2012 kentucky derby hats

This may be the largest hat worn at the 2012 Kentucky Derby. I hope whoever sat behind this lady was wasted, because they sure as hell didn’t see no horse race.

4. The Jester

#4 crazy weird funny stupid 2012 kentucky derby hats

Methinks the lady would fit right in at a Renaissance fair.

3. The Camera Hat

#3 2012 kentucky derby camera hat

At #3 we get a two-fer. The dude’s camera hat gets top billing, but the lady’s whatever-that-is hat is also quite the spectacle. Together, they’re an amazing pair.

2. Barbie Hat

#2 barbie hat 2012 kentucky derby crazy hats

The woman wearing this hat is from Las Vegas, and her name is Alison Callaway. (Note to self: if at Kentucky Derby wearing silly hat, never give name/personal info to photographers taking photos. Potential embarrassment.)

1. The Flamingo Lady

#1 crazy weird funny stupid 2012 kentucky derby hats flamingo hat

A couple years back this woman wore a hat with one flamingo to the Kentucky Derby. This year she figured it was time to up the ante. So she went with two flamingos. It’s a good thing, too. Without that second plastic bird, this lady wouldn’t have cracked the top five.