The Kentucky Derby 2021

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As much as the Kentucky Derby is about the horse race, the real spectacle is the fashion and more specifically the hats! Since the inaugural race in 1875 at Churchill Downs, a colorful punch of ornate hats and hair accessories have been worn by the excited crowds and fashionable elite. 

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Churchill Downs founder, Col. Meriwether Lewis Clark Jr. was adamant about rewriting the narrative around horse racing, which was considered a dangerous sport and came to the hypothesis that fabulous women wearing fashionable clothes could help, and it did! He and his wife had traveled to Europe in the years prior to the first Kentucky Derby and they were inspired by the traditions and decorum shown at the Longchamp Racecourse in Paris and Epsom Downs in Surrey, England.  It was not simply about the horse race, it was about the pageantry and grandiosity of the spectators and when they began planning the Kentucky Derby, he wanted the Kentucky Derby to have a similar tempo. So, “He loaded up a wagon full of high society women and they were going door-to-door telling their friends, ‘We’re going to have a picnic at the racetrack,’” an excerpt taken from the Kentucky Derby Museum. There is also a superstition that, the bigger the hat, the better your luck on your bet, and many onlookers will pay homage to their horse's silks by incorporating its color into their outfit for an additional dose of goodluck and sportsmanship. You wear your Yankee hat to the baseball game and you wear your horse's silk colors somewhere on your very wide brimmed hat. 

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The tradition of sporting a hat when attending the Derby or a Derby party remains intact to this day, and as a bonus keeps our faces out of the sweltering sun while we sip our mint juleps. (If you are looking for a recipe for mint juleps and other delicious spring cocktails click here!) Unfortunately we were not at Churchill Downs this weekend to watch the race, we dressed up for our at home watch party!

Congratulations to Medina Spirit, ridden by jockey John R. Velazquez, for winning the 147th Kentucky Derby! This is jockey John R. Velazquez’s fourth Kentucky Derby victory. We look forward to seeing both horse and jockey race for the triple crown.

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Take a look at our highlights of some of the fun fashion moments in the Kentucky Derby’s long history.

2021 Kentucky Derby Court

2021 Kentucky Derby Court

(Courtesy of the Kentucky Derby Museum)

(Courtesy of the Kentucky Derby Museum)

Star Jones at the Kentucky Derby in 2013

Star Jones at the Kentucky Derby in 2013

Queen Elizabeth II at the 2007 Kentucky Derby

Queen Elizabeth II at the 2007 Kentucky Derby

Supermodel Coco Rocha at the Kentucky Derby in 2013

Supermodel Coco Rocha at the Kentucky Derby in 2013

Supermodel Kate Upton at the Kentucky Derby in 2015

Supermodel Kate Upton at the Kentucky Derby in 2015

Gayle King at the Derby in 2016

Gayle King at the Derby in 2016

Actress and producer Lynn Whitfield at the Kentucky Derby in 2008

Actress and producer Lynn Whitfield at the Kentucky Derby in 2008

Layla Ali at the Kentucky Derby in 2018

Layla Ali at the Kentucky Derby in 2018

Model Lindsay Ellingson at the Kentucky Derby in 2015

Model Lindsay Ellingson at the Kentucky Derby in 2015

Michelle Williams at the Kentucky Derby in 2019

Michelle Williams at the Kentucky Derby in 2019

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