The phrase "go big or go home" is taken quite seriously at Churchill Downs. The Kentucky Derby is not just the most iconic horse race in the world, it's also a fashion show with hats that are larger than life.
Since the very first race on May 17, 1875, Col. Meriwether Clark Jr. – founder of Churchill Downs and grandson of the famous explorer William Clark – had the vision of modeling the races after British horseracing. Those races had strict dress codes for men and women, and those dress codes typically included hats.
Have you picked out your hat yet? 👀#KyDerby pic.twitter.com/qeALmiTG4i
— Kentucky Derby (@KentuckyDerby) May 3, 2023
Men have the option of wearing fedoras or bowler hats, but women usually have more fun designs -- with the exception of guys such as Skip Koepnick.
The Kentucky Derby was televised nationally for the first time on CBS in 1952. Being on television encouraged people to step up their fashion game. British fashion has continued influencing attendees, as events such as the Royal Wedding in 2011 have helped keep the magic of hats and fascinators alive.
Hats aren't technically mandatory at the Kentucky Derby, but showing up without one is a major faux pas. Milliners are busy year round helping ladies at Churchill Downs look their best on race day.
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Christine Moore became the first ever featured milliner of the Kentucky Derby in 2018. She has designed hats for plenty of celebrities, including Barbie in 2009. Her advice for first time attendees is to be bold.
"To people who have never been before and are a little shy about their look: The worst thing you can do is be the plain girl at the Kentucky Derby. You can be the plain girl anywhere else, but not at the derby. It will ruin your day," she told CBS Sports.
"With the Kentucky derby specifically, somebody is always going to have a bigger hat than you, so always go a little more extravagant than whatever your look is because there is always going to be somebody who is more extravagant."
Churchill Downs spans 147 acres, which Moore said was important to keep in mind when thinking of what hat you're going to wear. She tells her clients to remember the scale of their room at home is not the scale of Churchill Downs.
Hats can run up to $1,000, but going big with 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 find stylish derby hats they could afford. The high school best friends made about 30 hats their first year. They started at Smith's grandma's condo before spending the next few years working from Bell's dad's basement.
This year, The Hat Girls signed a contract to be one of three featured milliners for the 2023 Kentucky Derby, along with Moore and Jenny Pfanenstiel.
The Hat Girls made 1,600 hats and fascinators for the 149th edition of the Run for the Roses, a process they said has taken them all year.
With over a decade of experience, Smith and Bell have noticed different trends. Colors and designs depend on what dress a woman is wearing, but it's clear some things are more prevalent in a given year. This upcoming weekend, the milliners are expecting to see a lot of neon colors such as chartreuse. The Hat Girls are also betting there will be a lot of fascinators.
"Fascinators in general get more popular every year. I think we really saw the switch with the popularity of Meghan Markle and Kate Middleton," Smith said.
"When we first 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 trickled over here. It took a little bit, but we sell more fascinators now than we do hats."
Bell explained that the growing popularity was also likely because as people were less afraid to try them, they realized fascinators can be more comfortable and easier to maneuver than hats, especially in a big crowd of people.
Fascinators can be a lot of fun as they allow designers to play more with the silhouette and shape a little bit more than hats.
For those who want the best of both worlds, there are also hatinators – which give the illusion of a large hat but the comfort of a fascinator.
There are no rules on style 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 her and her friends when she was in med school. She is now a double board-certified physician in radiology and nuclear medicine, but her career as a milliner also took off and she is currently one of the Kentucky Derby Museum's featured milliners. Kogan designed the hat that Miss USA 2021 Elle Smith wore in the Jack Harlow Churchill Downs music video.
When she is not helping people improve their health, she is helping them look more stylish. Kogan knows the Kentucky Derby is a big day for fashion and that it can be hard to figure some stuff out, so she sometimes posts videos on Instagram teaching people how to wear their hats.
With the growing popularity of fascinators, Kogan recommends taking bobby pins with you. One pin, she said, can make a big difference because it's almost invisible and it can add extra security and comfort.
There is also one little trick that makes a huge difference. Hats and fascinators – particularly the pech tyle ones – should not be too far back on your head. Instead, they must be resting on your forehead just above the eyebrow.
"As soon as you move it just a couple of inches in that position it just looks infinitely better. It just looks amazing," The Hat Doctor said.
The Kentucky Derby is the two most exciting minutes in sports, but festivities last much longer than that so comfort with a properly fitted and 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 entire outfit for the better. You can have an ok dress, or a pretty dress but not that exciting, but then you put on a gorgeous hat and you just look stunning," Kogan said.
"Why not? Why wouldn't you wear something beautiful and totally elevate your outfit to a new level."
