Two photos of couples at horse races. On the left a black and white photo shows a couple in 1912, on the right shows a modern day couple.

Iconic Style Trends of the Kentucky Derby Over Time

It’s known as “The Most Exciting Two Minutes in Sports,” The Fastest Two Minutes in Sports”, “The Run for the Roses,” and, of course, The Kentucky Derby.

The Kentucky Derby celebrates its 150th anniversary on May 4, 2024, when 20 3-year-old thoroughbreds compete for the prize and their place in history. But the day has become much more than a horse race. It’s become a social event, even a cultural phenomenon. 

Fashion takes center stage at the Kentucky Derby and captures the attention and imagination of race-goers before the bell rings to kick off the race. Let’s take a look at the fashion trends of the Kentucky Derby.

The Early Days of Fashion

Socialites dressed nicely at horse race in 1911.
Photo Credit: The Library of Congress, No restrictions, via Wikimedia Commons

In the beginning, Derby-goers donned themselves in class and elegance. Before the Derby, racetracks were seen as…less than glamorous. The founder of Churchill Downs sought to improve the overall image to follow in the footsteps of European tracks where the wealthy and the elegant were regular attendees. The word went out, and the trends indeed followed, with elaborate headwear to showcase wealth and status.

Getting Bolder Over the Years

Kentucky Guardsman Sgt. Bryan Ploughe, inquires patrons about the history and legacy of the women's hats at the 2012 Kentucky Derby May 5 in Louisville, Ky.
Photo Credit: Kentucky National Guard, CC BY 2.0 DEED via Flickr.

By the 1950s, Kentucky Derby Infield parties had become popular and the relaxed atmosphere led to more relaxed, and often homemade hats. Derby fashion continued getting bolder over the decades. Now you can often spot wild hand-crafted hats with racing themes or bright, extravagant flowers.

Three men with wild derby themed hats at the Kentucky Derby.

Derby Party Hats

Image Credit: Joanna Poe, CC BY-SA 2.0, via Wikimedia Commons
Woman wearing big green hat with pink dragonfly at Kentucky Derby.

Dragonfly Derby Hat

Image Credit: Kentucky National Guard Public Affairs, CC BY 2.0, via Wikimedia Commons
Woman in hat with bright yellow flowers blue bow and red rim at horse race.

Bright Flowers

Image Credit: Diane-Bondareff/Shutterstock.
Man wearing hat in the shape of Churhill Downs at Kentucky Derby.

Churchill Downs as a Hat

Image Credit: Benjamin Thomas, CC BY 2.0 DEED via Flickr.
Woman with beautiful brightly colored feathers on a Derby Hat wearing banner that says Kentucky Derby Festival Princess.

Derby Museum Hat Show

Photo Credit: Kentucky Derby Museum.

Featured Milliners and their stunning designs were on display at the annual Derby Museum Hat Show in March 2024.

Millinery Masterpieces

Elegant hats and fancy attire at the horse races
Photo Credit: Diane Bondareff Shutterstock

Derby hats are not merely accessories; they are millinery masterpieces, often crafted by skilled artisans who design and construct each hat by hand, incorporating luxurious fabrics, feathers, flowers, and intricate embellishments. 

Symbol of Southern Charm

Elegant hats at a horse race
Photo Credit: Diane Bondareff Shutterstock

Kentucky Derby hats embody the essence of Southern charm, with their vibrant colors, oversized brims, and intricate designs reflecting the elegance and sophistication associated with wealth and privilege. Large hats were typically worn in places of honor and respect, including churches, helping to change the image of racing.

Derby Hat Etiquette

An attendee at a horse race, wearing a fancy hat.
Photo Credit: D Snyder Shutterstock

There are unwritten rules governing Derby hat etiquette, including the importance of coordinating the hat with the overall outfit, ensuring it complements rather than overshadows the attire.

Men's Hat Tradition

A man in a hat at a horse race.
Photo Credit: D Snyder Shutterstock

While women's hats often steal the spotlight, men also participate in the hat tradition, favoring classic styles such as fedoras, Panama hats, boaters, and, of course, derby hats to complement their Derby attire.

Runway for Creativity

A lady in a hat at a horse race.
Photo Credit: D Snyder Shutterstock

The Derby serves as a runway for creativity, inspiring hat enthusiasts to push the boundaries of design with avant-garde, whimsical, and sometimes outrageous creations that reflect their individuality and artistic flair.

Celebrities and Fashion Icons

Her Royal Highness Queen Elizabeth II smiles during a visit in London.
Photo Credit: Alessia Pierdomenico Shutterstock

Celebrities and fashion icons often make headlines with their fashion choices, setting trends and influencing mainstream fashion with their bold and glamorous choices. The Kentucky Derby is no exception, welcoming guests including Kim Kardashian, Miranda Lambert, Jason and Brittany Aldean, and the late Queen Elizabeth II.

The Cost of Making a Statement

young beautiful couple smiling and laughing while wearing flower hats at the Dubai World Cup Horse Race
Photo Credit: Ayotography Shutterstock

While hats can be purchased online for mere dollars, the average custom-made hat costs around $500. Of course, you can spend as much as you want to make the statement you want. At the Melbourne Derby in 2014, Australian model Kate Peck sported a $3-million hat that was adorned with 1,264 diamonds and set with a 37.53-carat beryl jewel.

Men Get Dressed Up, Too

Men's Derby Fashion with Bowties
Photo Credit: Nmorguelan Shutterstock

Fashion statements aren’t only reserved for women. The men of the derby get decked out as well. Bright and bold colors are a mainstay, with hats and bowties as accessories. Where else can you find such dapper looking men than the Kentucky Derby?

Big, Bold, Beautiful

Elegant and colorful hats at a horse race
Photo Credit: Diane Bondareff Shutterstock

The Kentucky Derby is everyone’s chance to go all out. There’s little to be seen in “reserved” fashion. Bold colors, big hats, and playful attire are the standard for everyone, although men generally have few hat choices.

Sunglasses

A woman attends horse-racing derby in Vancouver, Canada
Photo Credit: Sergei Bachlakov Shutterstock

Everyone wears sunglasses at the Kentucky Derby. But if you forget yours, you can pick up this year’s 150th-anniversary glasses at the gift shop.

Cigars and Kentucky Bourbon

Man sommelier pours Woodford bourbon whisky at booth of 4th Ukrainian Whisky Dram Festival organized by Good Wine company in Artistic Arsenal.
Photo Credit: Sergiy Palamarchuk Shutterstock

It may not be fashionable everywhere, but cigars and bourbon are part of the Kentucky Derby. Woodford Reserve has been the presenting sponsor of the Kentucky Derby since 2018 and recently signed on for the next five years. Cigar smoking is permitted in all open-air areas of Churchill Downs. Ted’s Cigars offers the Kentucky Derby Cigar, the official cigar of the derby for the past 15 years. 

A Legacy of Elegance and Glamour

A group of fashionable well dressed women pose whilst enjoying the social atmosphere at Market Rasen Races Ladies Day : Market Rasen Racecourse, Lincolnshire, UK
Photo Credit:
Mick Atkins Shutterstock

Above all, the tradition of fun and formal wear paired with flamboyant hats at the Kentucky Derby is a legacy of elegance and glamour. The timeless allure of the most exciting two minutes in sports and the spirit of celebration that accompanies this American tradition gives Derby-goers the freedom to express themselves. Have fun with your outfit and add some color to your wardrobe, whether you’re at the derby or watching from home.

Behind the Scenes at Churchill Downs

Entrance to Churchill Downs featuring a statue of 2006 Kentucky Derby Champion Barbaro.
Photo Credit: Thomas-Kelley-Shutterstock

A small army works behind the scenes to make the Derby possible. Here's what they do!

Author: Todd Rowley

Title: Copywriter

Expertise: social services, transportation, mental health

Todd Rowley is a copywriter and content writer. He’s an unabashed introvert, an only child with a curious spirit, and a lover of the Oxford comma. Originally educated as a Child and Youth Worker - spending more than 25 years in the field - he also dabbled in Religious Education and Communications Studies.