The 2026 Kentucky Derby is less than 2 weeks away.

Horse racing enthusiasts around the world are preparing for the Most Exciting Two Minutes in Sports.

And, for many of these fan’s part of their prepping includes choosing the appropriate hat for the Run for the Roses.

It doesn’t matter if Derby fans will be at Churchill Downs or a Kentucky Derby watch party, their outfits should include some sort of headwear.

You can’t think of the Kentucky Derby without thinking of hats. From the simple sunhat to the larger-than-life fascinator, everyone shows up to the Derby festooned in their favorite headgear.

As you prepare to don your Kentucky Derby best, you are probably wondering about this iconic chapeau tradition.

Just how did this famous tradition get started and what made it so big that even Queen Elizabeth II donned a red-ribbon bonnet when she attended the Kentucky Derby in 2007? 

The idea of the Kentucky Derby hat has been around since the beginning of the event when Colonel Meriwether Clark Jr. decided to model the races after British horseracing- specifically the Epsom Derby.

The Brits had a strict dress code for both men and women on race day, including hats.

The first women in attendance to the Kentucky Derby were socialites so it was no surprise when race day fashion became almost as big as the race itself.

During the 1960s, the hat fashion grew at Churchill when people started changing up the typical fashion and the televised Derby encouraged people to stand out.

These days, both men and women are encouraged to show off their favorite topper and as the years have gone by the hats get bigger and crazier.