Fashion
Kentucky Derby 2023: Why hats, flashy headgear are synonymous with the Run for the Roses

The phrase “go big or go home” is taken very seriously at Churchill Downs. The Kentucky Derby is not only the most iconic horse race in the world, it is also a fashion show with larger than life hats.
From the very first race on May 17, 1875, Colonel Meriwether Clark Jr. founder of Churchill Downs and grandson of famous explorer William Clark had a vision to model racing after British horse racing. These races had strict dress codes for both men and women, and these dress codes usually included hats.
Men have the option of wearing fedoras or bowler hats, but women generally have more fun designs – except for men such as Skip Koepnick.
The Kentucky Derby was nationally televised for the first time on CBS in 1952. Being on television encouraged people to step up their fashion game. British fashion continued to influence attendees, as events such as the Royal Wedding in 2011 helped keep the magic of hats and fascinators alive.
Hats aren’t technically required at the Kentucky Derby, but showing up without a hat is a major faux pas. The milliners are busy all year round helping the ladies of Churchill Downs look their best on race day.
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Christine Moore became the first-ever Kentucky Derby milliner in 2018. She has designed hats for many celebrities, including Barbie in 2009. His advice for new entrants is to be bold.
“To people who haven’t been there and are a little shy about their looks: The worst thing you can do is be the regular girl at the Kentucky Derby. You can be the regular girl anywhere. somewhere else, but not at the derby to ruin your day,” she told CBS Sports.
“With the Kentucky Derby in particular, someone will always have a bigger hat than you, so always be a little more extravagant than your look, because there’s always going to be someone extravagant.”
Churchill Downs is 147 acres, which Moore said was important to keep in mind when thinking about what hat you’ll be wearing. She tells her clients to remember that their bedroom scale at home is not the Churchill Downs scale.
Hats can cost up to $1,000, but scaling up your look doesn’t always require a big budget.
Kate Smith and Rachel Bell, better known as The Hat Girls, started making hats in 2010 when they couldn’t afford stylish bowler hats. The high school best friends made about 30 hats their freshman year. They started in Smith’s grandmother’s condo before spending the next few years working in Bell’s father’s basement.
This year, The Hat Girls have signed a contract to be one of three featured milliners for the 2023 Kentucky Derbywith Moore and Jenny Pfanenstiel.
The Hat Girls made 1,600 hats and fascinators for the 149th annual Run for the Roses, a process they say took them all year.
With over a decade of experience, Smith and Bell have noticed different trends. Colors and patterns depend on the dress a woman is wearing, but clearly some things are more prevalent in any given year. This coming weekend, milliners expect to see lots of neon colors like chartreuse. The Hat Girls are also betting that there will be plenty of Fascinators.
“Fascinators in general are getting more popular every year. I think we’ve really seen the change with the popularity of Meghan Markle and Kate Middleton,” Smith said.
“When we started, women were afraid to wear fascinators because they thought they looked silly on their heads. Then, with the popularity of (the British royal family), they kind of got infiltrated here. It took a bit, but we sell more fascinators now that we make hats.”
Bell explained that the growing popularity was also likely because people were less afraid to try them on, they realized that fascinators can be more comfortable and easier to maneuver than hats, especially in large crowds of people.
Fascinators can be a lot of fun because they allow designers to play more with the silhouette and shape a bit more than hats.
For those who want the best of both worlds, there is also hateful which give the illusion of a large hat but the comfort of a fascinator.
There are no styling rules with hats, fascinators, or hatinators, but there are definitely right and wrong ways to wear them.
Ilana Kogan, also known as The Hat Doctor, started making hats for herself and her friends when she was in medical school. She is now a doctor with a degree in radiology and nuclear medicine, but her career as a milliner has also taken off and she is currently one of the Kentucky Derby Museum Featured Milliners. Kogan designed the hat Miss USA 2021 Elle Smith wore in the Jack Harlow Churchill Downs music video.
When it’s not helping people improve their health, it’s helping them look more stylish. Kogan knows that the Kentucky Derby is a big day for fashion and that some things can be hard to figure out, so she sometimes posts videos on Instagram to teach people how to wear their hats.
With the growing popularity of fascinators, Kogan recommends taking bobby pins with you. A pin, she says, can make a big difference because it’s almost invisible and can add extra security and comfort.
There is also a little trick that makes a huge difference. Hats and fascinators, especially pech-style ones, should not sit too far back on your head. Instead, they should be resting on your forehead just above the eyebrow.
“As soon as you move him a few inches in that position, he looks infinitely better. He looks amazing,” The Hat Doctor said.
The Kentucky Derby is the most exciting two minutes in the sport, but the festivities last much longer than that, so comfort with a well-fitting, lightweight hat is crucial.
Whatever you decide to wear, all the milliners echoed the same advice: don’t be afraid to have fun with hats.
“Don’t be nervous. It totally changes your outfit for the better. You can have a proper dress or a pretty dress but not that exciting, but then you put on a beautiful hat and you just look stunning,” Kogan said. .
“Why not? Why don’t you wear something nice and totally elevate your outfit to a new level.”
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