May 04, 2018

The 144th Kentucky Derby takes place in Louisville tomorrow, Saturday, May 5th. As such, we’re getting two big drankin days in one—Cinco de Mayo and the Derby, in an event many are simply calling “Cinco de Derby.”

We can only imagine that the outfits—and especially the derby hats—will be wilder than ever tomorrow, as folks both in Kentucky and across America ingest an almost obscene amount of mint juleps and margaritas. To celebrate in advance, we’re taking a look back at some of the finest “fashion fails” the Derby has had to offer us. And yeah, we know, many of the Derby looks are self-aware (particularly the hats), but that doesn’t make some of them any less spectacularly odd and cringeworthy.

Let’s go!


1. Joey Fatone 

Former NSYNC member, Joey Fatone, needs to say “bye, bye, bye” to that getup. (Wooo, did ya see what we did there?!)


2. Kid Rock

He gets a point for color coordination but you just gotta question the wisdom of the perforated, semi-transparent polo.


3. Can a Derby Hat Be Too Big? 

This young lady sought to answer that question.


4. Johnny Weir

This is one of those where we can’t actually tell whether the hat is being worn in jest or not (we’re leaning toward no), but it looks like a large bird has taken up residence atop Mr. Weir’s head.


5. “The Beardilizer” 

This guy is 100% in on the joke that is his outfit. Still, it’s too wondrous for us not to feature—that beard is everything.


6. Happy Thanksgiving?

The Derby takes place in late spring but this woman went with drab neutral colors. It looks more like a centerpiece at a Thanksgiving table.


7. Welcome to Mardi Gras

Image Credit: Dylan Buell

Pretty sure these guys showed up at the wrong event.


8. The Derby Derby Hat

A very awkward hat depicting the derby itself. We actually dig it—we’re only concerned that it must have been hell for this nice lady to navigate the crowds with it on.


9. A Fake Head 

Image Credit: Dylan Buell

Look closely—this derby hat has a fake head mounted on the back of it. We need say nothing more.



10. Pretty in Pink

There’s just so much going on here. We’re completely overwhelmed.


11. Pretty in Plaid

Oh, Gronk. Always doing the most.