This distinctive fashion sense is built upon Kentucky Derby Founder Colonel Lewis M. Clark, Jr.’s original intent — to create an occasion that was inspired by European horse racing that would be both opulent and luxurious yet comfortable for spectators. Documented accounts from as early as 1901 describe Kentucky Derby masses as men and women done up in elaborate pastel attire. Because the event is held in May, spring-inspired frills like gloves, hats and parasols have always been hallmark accessories.
But the most famous element of Kentucky Derby Fashion is undoubtedly the women’s hats. Often custom-designed or handmade for the occasion, these outfit toppers can be true works of art. Typically, women don Southern-inspired, wide-brimmed hats that have been embellished with anything from whimsical flowers and feathers to miniature renderings of the famous Churchill Downs, proving that when it comes to Kentucky Derby hats, bigger and more elaborate is always better.
During modern derbies, men have also walked the red carpet in their own selection of caps. Men’s Kentucky Derby hats are often typical to the South, like fedoras and floppy brimmed hats made from appropriate materials like straw, linen or cotton. Men can get away with less adornment for the occasion, but some derby dudes have been seen sporting super wild and whimsical caps as well.
