Fashion
25 Craziest Kentucky Derby Hats Of All Time, So You Can Keep The Competition In Mind This Weekend
If you don’t have your Kentucky Derby outfit all squared away for this weekend, you’re behind. In case you need a bit of time to catch up, I’ve gathered an official ranking of the 25 craziest derby hats, just so you know your competition for this weekend. Because, if you’re not wearing the craziest hat at the party, what’s even the point of getting out of bed this Saturday?
While many celebrities flock to Kentucky for this event, sometimes it’s the local, unknown individuals with the wackiest ensembles. And with many resources for DIY, hat tutorials, and past celebrity derby pictures to help you out, there’s really no excuse for phoning it in.
Keep in mind as you scroll through this slideshow that the crazier the hat is, the higher it’s ranked. The Kentucky Derby is an annual excuse to pretend to be a part of the royal family and sport some serious headgear in public, except that these are hats on steroids. Take a look at what you need to live up to for the big race.
The Classic Baseball Cap
Just kidding! I felt it was necessary to list all the hats you may see at the Derby. Baseball caps are pretty tame, but I’m a fan of them.
The Round Hat
While this hat is certainly large and beautiful, it’s not that car-azy. I know you can do better than this.
The Kris Jenner
She has the family’s reputation to uphold and she showed up to the 2014 Kentucky Derby in this basic hat. I expected more from someone adjacent to the Kardashian Klan.
The Mega Round Hat
Well, the size is certainly a step above the previous one. This hat is noteworthy for its functionality. Kentucky is home to a brutal, Midwestern sun. Anyone sporting this does not have to worry about sunburn on her back! However, this hat could have been spruced up a bit to make it even wilder.
The Joey Fatone
I’m sure guy’s have slimmer pickings when it comes to Derby hats, but if Johnny Weir can pull of a fantastically crazy hat, any guy can. I expected more from a former boy band member who used to wear a red leather tuxedo.
The Classic
A big, round hat with a bow or flower on top will never go out of style at the Kentucky Derby, but you may also look like thousands of the other women and children there. Go nuts!
The Tara Lapinski
This is a slightly version of the classic hat, because of the giant flower on top.
The Matching Flower & Lipstick
The brim of this hat is unexpectedly sheer, and matching this woman’s lipstick to the flower in her hat was a total pro move.
The Angela Zatopek Mini
The mini derby hat is adorable, cute, and unexpected, although maybe not as over-the-top as some of the other options.
The Cheryl James Bow
Why bother to put a bow on your hat when the bow could just be the hat?
The Basic Hat, Awesome Makeup
His hat isn’t super exciting, but when you add that makeup, you have a winner.
The Lauren Conrad
She gets bonus points because she probably DIY’ed this hat in an hour.
The Beaded Trim
Everyone is going to hear it when her horse wins.
The Miranda Lambert Inversion
Gotta love Lambert’s inversion of the classic Derby hat with the flower underneath the brim, rather than on top.
The Megan Ducharm
Ducharm took her hat to the next level by inverting the rim. Totally unexpected and unique.
The Full-On Garden
Why have one flower on your hat when you can have like a thousand?
The Boa
There’s is a boa on top of her hat. ‘Nuff said.
The Kelly Anne Beile
My eyes don’t know where to look or how to keep up with the many feathers — and I love it.
The Reverse Mask
I’m not going to lie, I’m terrified.
The Very Literal Hat
This guy is doing the Kentucky Derby all sorts of right. Take that, Fatone.
The Johnny Weir
It’s like a unicorn is trying to escape from his head.
The Other Very Literal Hat
I hope this guy got in for free.
The Cartoonish Floral
When you bring facial paint into the mix, there really is no competition.
The Couple Box Hats
It literally doesn’t get better than this.
The One Covered In Money
The betting gets real when you put the money on your hat. People have no choice but to take you seriously.
