What Were They Thinking? Breaking Down the Most Ridiculous Kentucky Derby Hats
By nesbittandy1
The Kentucky Derby is one of the greatest events of the year, full of gambling, bourbon, and… hats.
Lots and lots of hats.
The tradition of wearing ridiculous hats to the Kentucky Derby is definitely… something, as people show up with some crazy things on their heads.
So while we get ready for the 144th Derby this Saturday, let’s have some fun breaking down the strangest headwear from recent years.
On second thought…
You can tell just by looking at this woman’s face that the idea of this hat was a lot better than the actual existence of this gigantic hat. Not really ideal for getting through big crowds and you gotta believe it’s gonna lead to a stiff neck on Sunday. Hey, we all make mistakes.
Hurry up and take the picture
“Did you get it? Did you take the picture? You got it, right? Good, time for me to take this thing off.”
Every Saturday is Derby Day
Something tells me this isn’t her Kentucky Derby hat but rather just her Saturday hat.
YOLO!
This guy is either living his best life (RN!) or he lost a bet. Or he’s just really enjoying whatever is in that bottle. Probably a mixture of all three.
Good luck with that
It’s all fun and games until you forget to duck when entering a port-o-potty after a few too many mint juleps and your roses end up on that nasty floor.
We will remember you
Do you remember former Kentucky Derby champ Barbaro? We sure do, and so does this woman on the right with her incredible tribute to one of the best to ever do this thing. We miss you, Barbaro. RIP.
The “happy wife, happy life” look
You know that’s a phrase this guy not only uses, but also feels like he’s one of the first to say it when he not only proudly says it to friends, but also has it as the first line in his email signature.
The “no regard for human life” look
Thoughts of Kevin Harlan calling that epic LeBron James dunk from years ago pop up here, as this woman clearly isn’t concerned about the people sitting behind her and their ability to see what’s actually going on in the race.
The “money” look
Not everything in this photo is real. We’re talking about the money on the hat, of course.
Let there be… dolls?
Ever wonder what to do with all the dolls you have sitting nicely on top of your dresser? You know, the ones you polish every morning while sipping on tea? No, just this woman?
This seemed like a fun idea in the group text
It’s all fun and games in a late-night group text thread until suddenly you’re outside on a beautiful spring day wearing ponies and flowers on your head. The guys on the left and middle know what we’re talking about.
State of confusion
The woman in the orange is all of us right now. Gotta think the fella wearing this sizable hat tipped over and spilled his Pepsi all over the ground moments after this photo was taken. And is that a remote control in his hand?
Tough to tell secrets
These two women have a lot going on on top their heads, which makes it tough for them to whisper back and forth about something they think about a mutual friend (not pictured) who’s in their group.
The easy to find friend
The twin spires that make up the iconic grandstands at Churchill Downs are truly beautful. Make a hat out of them, though, and they serve as an easy way to find your friend in the middle of a boozy crowd.