The first Saturday in May, all eyes are on Louisville’s Churchill Downs for the annual Kentucky Derby which is one of America’s oldest sporting events with the first taking place in 1875 with the first started by Meriwether Lewis Clark Jr. (whose grandfather was William Clark of the Lewis and Clark expedition). Seriously, it predates the Super Bowl. Now the Kentucky Derby is the first of the major Triple Crown horse races in which the horses and their riders must race along a 1 1/4 mile stretch. But unlike NASCAR, it’s just the one time and lasts for a few minutes. So no falling asleep at the TV screen there. However, the winner is usually the favorite for the other two Triple Crown races like the Preakness in Maryland and the Belmont States of New York as well as gets covered in roses. The horse winning these races wins the Triple Crown, which last happened in the 1970s. Now after the Kentucky Derby is a 2 week long Kentucky Derby festival. Still, there are a lot of traditions associated with the Kentucky Derby such as mint juleps, burgoo, gambling, and rich people. Yet, one particular tradition standing out is how many spectators tend to wear large ridiculous hats. So for your reading pleasure, here is an assortment of Kentucky Derby hats.
1. Now this guy loves flowers in his hat and seeing dollar signs.
Yes, wearing ridiculous Kentucky Derby hats no longer seems limited to women anymore. I mean this guy seems more suited for a different sporting event or night club.
2. Of course, you can’t kick off the Kentucky Derby Day without breakfast.
Not sure if this hat is from the Kentucky Derby. Yet, since it’s a hat with a heart attack inducing breakfast on it, I’ll put it on there. Fitting since obesity is a big problem in Kentucky anyway.
3. Why have a flamingo on your lawn, while you can have one in your hat?
Now this hat is outrageous enough without the flamingo. But with it, it’s just tacky. Even more ridiculous is that the flamingo also has a hat, too.
4. Ever get the feeling that some people have horses flying around their heads?
Now this guy has a cowboy hat on with roses and horses spinning at the top. Of course, there are only two seats on this small carousel if it is one.
5. Since Kentucky is the Bluegrass State, it’s only fitting to have wear a hat of blue cheese.
And what better hat of blue cheese than one that almost resembles Mt. Rushmore on a platter? Seriously, it kind of does if you think about it.
6. When it comes to top hats, the taller the better.
If it weren’t for the roses, you’d think this guy’s hat came straight out of a Dr. Seuss story. But it goes great with his outfit.
7. If one flamingo won’t make your hat look ridiculous, more will certainly do the charm.
Flower garden flamingos: Making Kentucky Derby hats and gardens tackier since someone thought that they’d make a great decoration for their landscaping.
8. Roses, beads, and pins will certainly make this woman a spectacle at the derby.
Too bad that the Amazing Karnak was planning on wearing the same thing. Of course, most people don’t know who the Amazing Karnak is since he’s one of Johnny Carson’s characters. Yeah, hasn’t been around since the 1990s.
9. Make sure the roses on your hat have little horseman on them.
Now I don’t know what to make of that. Because little horsemen simply don’t jump out of roses as far as I know. Except maybe in acid trips or something.
10. In the Kentucky Derby, your hat can never have enough flowers or feathers.
Now this seems like a fancy winter hat at this angle. But it’s basically made for spring. Still, it’s as utterly tacky as you’d expect Lady Gaga to wear it at an awards ceremony.
11. Since spring is the season of flowers, why not spring into the Derby in pink?
“Oh, shit. Seems like I forgot to put on some peacock feathers on this to make it seem more outrageous. Now Cindy’s out there topped with a showgirl’s hat from Las Vegas.”
12. When it comes to derby hats, you can use almost anything, even tablecloths.
Now this seems like she’s traveling in an exotic land, perhaps during the late 1800s. Then again, it does look like a creative arrangement of a table cloth.
13. Since the Kentucky Derby is a horse race, it seems appropriate enough to wear a horse’s head for the occasion.
Now that looks like a horse’s head you’d get from Amazon or something. Still, seeing it eat roses is kind of creepy if you think about it.
14. As far as flowers go, the bigger the better.
And this red flower seems to cover most of this woman’s hat. Hope some bee doesn’t mistake it for the real thing.
15. During the Kentucky Derby some people drink while others seem all corked out.
Let’s hope that the corks she used on this hat came from a craft store. Because if not, she might need to go through a Twelve Step program.
16. Some people tend to be private about their boudoir while this woman as a miniature version of hers out in the open.
I’m not sure which is more outrageous having a bathroom on your head or all the blue stuff surrounding it. Seriously, it just seems so ridiculous on sight.
17. Of course, every look has to go with the right kind of curls.
Now if these curls were any smaller, I would’ve mistook them for wood shavings. Hope she doesn’t run into low doorways.
18. Nothing makes a nice Southern plantation home than a grand staircase.
But when it comes to this woman, the grand staircase is pink and purple as well as on her head. But I don’t know if this staircase leads to heaven or nowhere.
19. When it comes to the wild Kentucky Derby fashions, even the sportscasters like to show off.
NBC sportscaster Bob Costa looks so stunning in Johnny Weir’s white hat. Not sure if it matches his suit though.
20. While some don hats of horse’s heads, others don those of jockeys.
Hope this woman didn’t get that head from her job at the DMV. Then again, she seems a bit too rich to have a job there from how that hat is decorated.
21. People come from all over the country for the Kentucky Derby. This woman is from Wisconsin.
And she’s wearing her cheese head coiffure in all its Greenbay Packer glory. Seriously, whenever I see a cheese head, I think of the Greenbay Packers.
22. What better hat for the Kentucky Derby than a straw bonnet of a horse?
Yes, this guy sure looks pretty with a horse bonnet that has pink lilies on its ears. Also, has a rabbit’s foot on it for luck. Guess he has money on a horse.
23. While the official Kentucky Derby drink is mint juleps, this lady prefers to wear a martini glass.
Well, I’m sure she doesn’t drink out of the thing,. But if she does, then she might have a problem.
24. Just drinking mint juleps with a jockey and horse by his sides.
Seems like the jockey and horse are chilling right by his riding helmet. Let’s hope he doesn’t have money on a horse and is just there for the fun of it all.
25. Of course, you always need your hat to match your outfit at the Kentucky Derby.
Looks like this will be Lady Gaga in a few decades. Seriously, I can totally see her wearing something like that an awards ceremony or public appearance.
26. No post on Kentucky Derby hats would be complete without one of a mint juleps.
Of course, that’s not a real mint juleps. But it looks pretty crazy yet appropriate at the same time.
27. It helps if the fringe on your hat matches the cuffs on your dress.
And she seems to have obtained the fuzzy trim from the rare Truffula tree. Of course, she probably had to spend a fortune on it as we know from The Lorax.
28. Pink flowers and black feathers, what can possibly go wrong with that?
I’m not sure if I can call this pretty since it seems to come from something you’d see a Star Trek alien wear. Seriously, the feathers are sticking out of the flowers.
29. When it comes to hair extensions, you can certainly go wild.
Now this is the kind of Kentucky Derby hat you’d see in a Lady Gaga music video or at a show in Las Vegas. Still, it’s quite hideous.
30. Some flowers just simply go well in a box. Some in planters. And some in hats.
I’m sure the flowers aren’t real but they’re certainly outrageous compared to the horse. Man, that hat is massive.
31. I call this look the Las Vegas showgirl.
And the fact this hat is worn by a guy makes it even funnier. Seriously, he’s bound to make Native American casino owners pissed off over cultural appropriation.
32. When it comes to Kentucky Derby hats, some are bound to make other spectators a little uncomfortable.
Yeah, if I was sitting next to a guy with an old timey camera hat and wearing sunglasses, I’d assume he was working for some covert organization. Seriously, he give me the creeps.
33. Some people enjoy the Kentucky Derby so much that they have to wear Churchill Downs on their heads.
Because why have a hat of a horse’s head when you can have one with 2 steeples? Of course, she might poke somebody’s eye out.
34. Of course, this woman is setting a record with her LP hat.
Hope the album in question isn’t of great quality, music wise. Seriously, I wouldn’t want to wast a good album on a hat if I were you.
35. Hey, I didn’t know that you can wear giant candy wrappers.
Hmm… I know the fashion industry can churn out some crazy shit these days. But I’m not sure if I’d want to be caught dead wearing a candy wrapper hat should a horse run over me at the races.
36. Eeek! Is that a spider on her head? Oh, God, take it away!
Sure she may think she’s glamorous, but her hat resembles some kind of giant spider that’s just escaped from mad scientists laboratory. Wouldn’t be surprised if it was radioactive.
37. With a hat like this, no one will get lost or forget the time.
Unfortunately, this sundial hat isn’t 100% accurate. But I’m sure you can see it from a bird’s eye view. Or not.
38. Of course, when looking at her hat, you’d swear to have seen it in a modern art museum. You probably didn’t know it was a hat to begin with.
Nevertheless, wearing a hat like this, and astronauts will be able to track your moves from space. Still, quite hideous.
39. Hey, I didn’t know they had a My Little Pony horse’s head hat. Guess every little girl wants one now.
Well, basically a hat for those who enjoy My Little Pony and The Godfather. Now Rainbow Sparkles will certainly make him an offer he can’t refuse.
40. Now this is the kind of Kentucky Derby hat I’d expect from a Tim Burton film.
From Huffington Post: “Originally designed to be worn by Helena Bonham Carter at the Oscars, this hat has found new life startling horses at Churchill Downs.”
41. What better way to grace the Kentucky Derby than wear a hat made from the precious feathers of your pet macaw.
Of course, it was a Norwegian Blue which is know for its wonderful plumage. But they do have a tendency of pining for the fjords. What? Are you saying that there aren’t any parrots in Norway? Well, you obviously haven’t seen Monty Python.
42. This guy seems to love roses so much that he had to have some tattooed on his face.
Doesn’t stop him from looking like some bum who was hired to wear such a ridiculous hat. Yeah, seems like he’s the kind of guy who attends the Kentucky Derby during his annual day of being in civilization.
43. After the Derby one of them is going to a mad tea party while the other will celebrate Cinco de Mayo by watching The Three Amigos.
Mad tea party or Three Amigos? Oh, what the hell, Three Amigos will always win every time for me. Seriously, that movie is a classic.
44. The Louisville mayor and his entourage.
Nevertheless, Louisville’s mayor has an ego about a mile wide. So on Kentucky Derby day, he thinks he’s the Pope.
45. I suppose this is the ice cream lady.
I don’t know about you, but she’s probably wearing the hat for the money. Bet the ice cream company is sponsoring this horse race, right? How else could she wear an ice cream cone on her head?
46. Seems like this woman decided to wear the same outfit she had on during the gala at the modern art museum.
Because how else could her hat resemble a piece of funky colored bacon with springs on it? Seriously, bacon doesn’t look like that.
47. Guess the ladies of the Red Hat Society aren’t wearing anything outrageous.
Oh, my mistake. Actually looks like something the Red Hat Society ladies might wear to a derby in a Dr. Seuss story for some reason. Then again, the feathers are just crazy on this one.
48. When it comes to roses at the Kentucky Derby, the bigger, the better.
And it makes you wonder how the rose can be so big and still stay on this woman’s head. Seriously, I really want to know that answer.
49. Some people just want to wake up and smell the flowers.
Some guys just want to wear a hat with the petals surrounding them. Sure this doesn’t make you look ridiculous (sarcasm).
50. I suppose that this guy is holding the cup.
Sure he may wear it on his head, but think of how many things he’s carrying in that. Hopefully, he doesn’t have any drugs in them. But I could be wrong.
51. Nothing shows your love for the Kentucky Derby than wearing a hat of dangling horses.
Okay, now I don’t know about you, but it seems that the horses are dangling from their necks. It’s like an equine hanging tree. Seriously, that’s messed up.
52. When it comes to Kentucky Derby Beer Pong, all the plastic cups have to have roses and mint juleps in them.
Of course, they may be empty for now. But after the Derby, well, I’m sure they’ll be filled with booze and be used for beer pong. Not sure about the roses though.
53. Of course, nothing shows your love for the Kentucky Derby than having your hat made from the feathers of your dead parrot.
Seriously, you have to wonder why people would think that using dead pets for fancy hats is a good idea. Also, this hat is beyond hideous, but here it is.
54. Care for a bee in your bonnet?
Hey, I didn’t mean literally, but what the hell. I mean it’s just an expression. You don’t need to take everything literally. Also, that bee is terrifying.
56. Can’t decide between 2 hats? Just glue them together and create an awesome megahat, or not.
Yeah, I think the white hat would’ve been better without the funky blue feathers plucked from a bird in Horton’s jungle. Hey, I’m just saying.
57. Finally, a hat with nothing unusual.
Oh, wait, that’s Joey Fatone from the 1990s boy band NSYNC. Still, you kind of wish they had reunion at the Kentucky Derby wearing hats like these.
58. Now the bowler hat is fine. The giant cigarette, large gemstone ring, and the fur coat on the other hand.
Seriously, if he’s not doing anything illegal or killing people, he’s probably a greedy corporate executive who treats his minimum wage workers like shit, is engaging in insider trading, has had a succession of trophy wives, and spends most of his time on his expensive yacht.
58. Who knew that the Ghost of Christmas Present was a fan of horse racing?
Guess a guy whose job is to haunt the dreams of miserly bankers on an annual basis needs some kind of pleasure in life. But still, he looked way cooler in A Christmas Carol.
59. Knowing that it was expected to rain in Louisville during the derby, Cyndi Lauper decided to dress accordingly.
Yes, that Cyndi Lauper. Yes, that hat resembles a UFO. And yes, it also doubles as an umbrella. Any questions?
60. Of course, this gigantic pink rose doesn’t make her hat look in any way cartoonish.
Uh, yes. it does. In fact, it makes the other gigantic flower hats look normal in comparison. Seriously, you’d swear it was genetically engineered by Monsanto.
61. May I present to you, the Green Bay Packers Ladies’ Auxillary.
Now regular cheese heads are one thing. But pink cheese heads? Now that’s really fucked up. Guess they really wanted to show their love for the Packers and wear hats that matched their outfits.
62. Now here is a hat in glorious purple.
From Huffington Post: “There was this giant purple monster with feathers and it was chasing me through my old high school.”
63. I’m sure those bright pink feathers will make any Kentucky Derby hat look gorgeous.
I’m sorry but I was wrong. It just looks like something you’d buy at a Halloween costume store, particularly if it comes with a matching pimp suit.
64. After the derby, this guy plans to take part in some secret cult ritual involving horses or something. Or maybe he’s just wearing a horse’s head.
Of course, it’s bound to bring some traumatizing memories for people who woke up next to a horse’s head in their beds. Kind of disturbing if you think about it.
65. Of course, when it comes to hat decorating, some people just don’t know when to stop.
Let’s hope Churchill Downs has high doorways so she doesn’t run into something. Still, if she was a man, you’d think she was compensating for something.
66. This woman is certainly an accomplished hunter for she had to shoot a lot of birds to make a hat like this.
Of course, when it comes to pheasant shooting, this lady tends to use a machine gun by the looks of it. Still, maybe she should’ve stuck to something more suited for spring.
67. Nothing shows your love for the Kentucky Derby than a hat with a horse’s head in a top hat on a platter.
I don’t know about you but I’m starting to get the kind of My Little Pony meets The Godfather vibe again. I wonder why. Still, it has some pretty disturbing implications if you ask me.
68. Of course, if it should rain in Churchill Downs, then I’m sure I’d like to get under this guy.
Nevertheless, if there be showers, this guy will certainly be very popular. I mean wearing a hat like that would make any guy a one man mobile pavilion.
69. I see that the horses are about to leave the gates.
My mistake. That’s just a guy’s hat. Yeah, I know it’s weird. But he really seems to be a big horse racing fan by the looks of it.
70. Won’t you give another mint julep for this Fairy Godmother?
Seriously, she went through all that trouble to get Cinderella to the ball. So she really can use a break. And so what if she likes to bet on horses and get drunk on mint juleps afterwards?
The Lone Girl in a Crowd 
I wouldn’t want any of these people to sit in front of me during the race. I bet the chiropractors there do a booming business. Those hats look heavy!
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