The Kentucky Derby, one of horse racing’s premiere events, takes place every year on the first Saturday in May. Held in Louisville, Kentucky, at Churchill Downs, it remains the social occasion of the season and plays host to a mix of ardent racing fans and members from high society. The Kentucky Derby is also known for its fashion, as the women in attendance wear an array of fabulous hats. Learn more about the history and the tradition behind these famed hats.


With glamorous clothes on constant display at the Ascot Racecourse in England, a link soon developed between high fashion and horse racing. The tradition jumped the pond and both elegant clothes and hats were on hand at the inaugural Kentucky Derby more than 100 years ago. When hats faded from the public’s everyday wardrobe, it seemed to increase the lavish nature of Derby Day hats. Wearing a hat only once a year made the occasion particularly special and extravagant results soon followed.


Although horse racing may be a science that involves handicapping odds and analyzing stats, it also involves a little bit of old-fashioned luck. In fact, some women believe that wearing their lucky hat to the Kentucky Derby can bring about a winning horse. Of course simply showing off your smart fashion sense remains the primary motivating factor for wearing such hats. These stylish bonnets allow women the chance to flaunt their impressive wardrobes amidst an elegant setting.


While some women may deem Derby Day as the perfect opportunity to flash their wealth, many see their hat as simply the ideal chance to project their personality. Derby Day hats are often viewed as an outlet for self-expression. For instance, loud and boisterous women may don extravagant hats, while quieter more reserved personalities tend to prefer conservative hats. Those eager for attention may drift toward outlandish designs, while fashionistas gravitate toward classically chic hats.


Your choice of hat depends on where you sit on Derby Day. Millionaire’s Row, a host of box seats attached to the grandstand and reserved for the wealthiest guests, features very elaborate and majestic hats on display. Meanwhile the infield projects an infinitely more relaxed setting. As a result, many of the hats in the inside portion of the track are a lot less grand. In fact many of the hats in the infield are downright silly and frivolous.


The most popular style of hats at the Kentucky Derby would have to be the Southern belle design. These oversized hats feature wide brims and often times come in the season’s most fashionable colors. Regardless of the specific style, many hats are dotted with satin ribbons, billowy feathers or silk flowers. Large bows may also appear weaved throughout the brim. On some occasions you may spot hats accented with short tulle veils over the front or back of the brim.