The 12 Most Ridiculous Kentucky Derby Hats

This weekend, our nation’s focus turns away from the crushing pain of existence and onto the dazzling display of surfaces being paraded at a Kentucky horse track. The derby is known for two things (three if you count the anticlimactic race itself): Mint juleps and big-ass hats. I lobbied to show 12 pictures of delicious-looking mint juleps for this piece, but my editor insisted that only functional and non-functional alcoholics would appreciate that article. I would argue that there are probably more of those people reading TPS than there are people who want to read my pithy remarks about derby hats but my rebuttal fell on deaf ears. The only way to know who’s right is to let it be known in the comments. Are you an alcoholic, a hat enthusiast, or both?

12.The Coco Chanel’s Nightmare Hat

That has to be Cruella de Vil’s hat, right? Right? What’s most upsetting about this hat is that there appears to be a cute girl under there, but the world will never know. Because all we get is an eyeful of big, dumb hat. Lame.

11. The Black Widow Hat

“Watch out boy, she’ll chew you up!” This hat looks a little more like the netting you sleep under in Sri Lanka to keep mosquitoes out than it does fashionable headgear. But as we embark on this journey, we will see that most of these hats don’t really look like much of anything. The nice thing is that she will also be able to wear this at Elton John’s funeral.

10. The Schizophrenic Peacock

Where does one purchase a single thing that she’s wearing? Jewelry on loan from the Nightmare before Christmas collection and pretty horsey picture on loan from the psych ward at Bellevue. The hat? The hat is made 100% from the afterbirth of Muppets. It’s VERY rare.

9. The Maddest Hatter of Them All

This hat is ridiculous; that’s not up for debate. However, its ridiculousness could at least be mitigated if this guy had an alcoholic beverage in his hand. With the booze: party guy. Without the booze: crazy person. There’s a reason there’s not a single woman around him. They’re terrified he’s going to drag them to his dungeon.

8. The Spinster Deluxe

I’m praying to all that is pure and holy that the “39” on her hat doesn’t refer to her age. If so…yikes. She, like everyone else at this damn race, has horses on her hat. But the million-dollar question is what’s behind those glasses. I’m guessing it’s Steve Buscemi’s eyes.

7. The Aquamarine Face-Strangler

I don’t know if I’m looking at the back, the side or what. What I do know is that this is the hat that Joseph Merrick would wear if he were to attend the Kentucky Derby. There’s something hideous going on under that “hat.” I just know it.

6. The Psychopath Cowboy Hat

His eyes are just in frame, giving this snapshot the same look as a horror movie poster. Those horses on the top appear to spin around, leading me to believe that this is what rich rednecks wear after they out grow propeller beanies.

5. The Acid-Trip-on-Your-Head

Roses and tie-dyed tank tops, together at last. Do you think this dude planned this outfit ahead of time, or he just rolled out of bed, shotgunned a FourLoko, then reached for whatever wasn’t covered in goat blood from the night before? Cause I think that’s EXACTLY how this wardrobe selection went down.

4. The Mugger’s Delight

There is a lot going on here. The inspiration here appears to be those big wreaths that are carried at policemen’s funerals, but with the tasteful addition of cash to the outfit. I’m trying to figure out what denomination those bills are if they’re even real at all. Best I can tell, they appear to have the likeness of John F. Kennedy on them. Suspect, lady. Very suspect.

3. The Jenny-McCarthy-Is-Hot-Even-in-a-Dumb-Hat

I don’t care if she refuses to vaccinate her children. She’s hot. Also, her hat kind of makes her look like she has an octopus on her head, which I really like. NEXT!

2. The Hats Next Door

You know that your event breeds a pretty effed up fashion culture when three Playboy Playmates show up and they are hands-down the most tastefully dressed women up in this piece. Also, with this picture, I can sort of pretend that Holly only has one leg, which makes me giggle. Don’t judge me.

1. The Greco-Roman Clusterf#@$

Is anyone willing to bet at 10-1 that this guy is not involved in a feud with some other family that lives just a Kentucky holler from him? He looks catatonic in this picture. Perhaps he actually dresses very tastefully, but in his weakened state, his grand-nieces dressed him up like this, and he was completely powerless to stop them. Or maybe there’s a Weekend at Bernies thing going on here. That would also explain the slack jaw and the thousand-yard stare.

Tags: hats, Kentucky Derby,