Kentucky Derby Styles Through The Decades


Fashion has always been an important part of the Kentucky Derby. After traveling to the famous Derby races in England and Paris in 1872, Col. Meriwether Lewis Clark Jr. decided to establish a similar high-profile horse race in America. He raised money for a racetrack and established it outside of Louisville, Kentucky. It became the iconic Churchill Downs, and held the first Kentucky Derby in 1875.


Over the centuries, fashion has provided us with some very questionable trends, but of all the fads, none are quite as odd as the “hobble skirt”. The name comes from the term for binding a horse’s hooves together to keep it from running off.

This snug-fitting frock, which hugged the legs and nearly bound the ankles, was quite the craze from about 1910 to 1913.


The “Flapper” looks of the 1920s was a dramatic change to the previous decades and saw much smaller cloche and bucket caps  that were worn with a dress and gloves or loose suits. Though the daytime event of the Kentucky Derby didn’t attract much of the flapper style for which the era is remembered, the attendees chose between formal suits or dresses to go with a range of fashionable hat styles.


Throughout the 1930s, hats and headpieces were more simple and blended in with the fashion of the time, rather than serving as stand-out accessories.

Loose suits and form-fitting dresses – particularly the “slip-on dress” – were all the rage, matched with ladylike cloche hats, elbow-length gloves and flowers worn as corsages.

Ms. Doris Murphy attending the Kentucky Derby, Louisville, Kentucky, 1938. (Photo by The Abbott Sengstacke Family Papers/Robert Abbott Sengstacke/Getty Images)


Style icons and celebrities of the time, like Carole Landis and Rita Hayworth, set trends with formal suits rather than day dresses.  Outfits were chic and clean with matching hats and often gloves.

Fashion At the Races


Until the 1950s, the focus was a bit more on the winning horse at the Derby, rather than a full-on fashion display, but that was about to change. Formal attire became more popular as post-war America ushered in a generation of women looking to dress for high society.  This was amplified by the opening of Millionaire’s Row, which was filled with glamorous dresses made from taffeta, lace, netting or chiffon.

Tea-length dresses were most common and cat-eye shaped sunglasses were abundant. It wasn’t until the 1960s when these conservative looks were traded for a more relaxed attitude and style of dress.

Most of these classic trends have cycled back. But you’ll notice that the ladies didn’t bring the wide-brimmed hats that were so common in the beginning of the century until television became more prevalent. The live broadcast of the event became a recipe for the fashionable to really put on a show!


The 1960s was an exciting time to be in the Western World. The brims on the hats got wider and more exciting. The designs started becoming much more creative as the hippy movement from the west coast began trickling in and encouraging wilder expressions in fashion. The fast-growing feminist movement pushed aside ‘typical’ outfits for more edgy looks, ranging from pantsuits to the miniskirt. An explosion of new styles became popular and women like Brigitte Bardot, Mary Quant and even Jackie Kennedy became the fashion icons of the decade.


Thanks to the relaxed stylistic movements of the 1960s, the 1970s saw an attitude at the races. Ladies boasted daringly short skirts and trapeze dresses with their fedora or “floppy” style sun hats. Yet, certain women longed to maintain the original Derby traditions, leading to an increase in the larger, more elaborate headpieces that you see present today.


In the 1980s, the Kentucky Derby became an even more popular event for the rich and famous. Actors and celebrities flocked to Louisville, Kentucky to show off their show-stopping hats. This decade may have seen big hair, but the hats were bigger. A lot of that influence was thanks to the popularity of Princess Diana and her John Boyd hats. Loosely fitted frocks and short cocktail dresses emphasized the ongoing excitement and free-spirit of the decade.


Hat styles continue to grow as much as the size of the brims. Select Derby-goers began to truly embrace their humor and some even take a comedic approach to their handmade designs.  Dresses continued to replace dress-suits for ladies while bold shapes and accessories were key.

2000 +

Although the general popularity of hats may have overall diminished culturally as a fashion trend, the tradition stays alive and well at the Kentucky Derby. In the 2000s, people flock to Kentucky and don ethereal cotton sundresses, bold-hued skirts – and even jumpsuits – with the most wild and expensive of headpieces. Dresses in all colors of the rainbow and bold patterns create a sea of color in the stands of Churchill Downs on the first Saturday of May.

Thanks to the popularity of Kate Middleton and Prince William’s royal wedding, impeccably designed fascinators and elaborate headpieces made a strong comeback. The Kentucky Derby is now becoming one of the most important events for milliners around the world.


Article courtesy of the Kentucky Derby:


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Written by Kaitlyn Fusco

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