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'Apex of society': How much Derby fashion has changed in the last 150 years

Fashion has changed a lot since the first Kentucky Derby in 1875, but one thing has been constant -- visitors, vying for the spotlight with iconic ensembles.

LOUISVILLE, Ky. — The real stars of the Kentucky Derby aren't found in the Paddock or on the red carpet. Instead, they're the style icons who manage to craft the most stunning, extravagant or outlandish race day looks. 

Even 150 years ago, in the earliest years of the race, Kentucky Derby Museum curator of collections Jessica Whitehead said the aim was the same. 

"Horse racing was a social sport, you were coming to see and be seen at this place that was pretty much the apex of society," she said. 

The clothes from those early years tell the stories of their time. Whitehead is in charge of preserving many such pieces and documenting their history at the museum. 

"There was a really significant transition in the way men and women were dressing in American culture in the transition from 1900's, 10's into 20's and 30's and that was the innovation of sportswear," she said.

Whitehead points to another shift in American fashion as the reason an iconic part of Derby culture began. 

"This whole idea of a Derby hat, that was a major change in Derby fashion history that came around right at this big transitional time in American culture," she said. 

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Whitehead notes during the 1950's and 1960's hats became less common in daily life. During that time, people began wearing them as part of Derby ensembles, even making them the star. 

"There's always been a tension between really traditional fashion and really traditional ensembles and sort of outlandish," Whitehead said. 

For many years, a wide brimmed hat was the standard look. Whitehead said more recently a European transplant, the fascinator, has come into fashion. 

The museum's collection includes many hats made for a day at the track, but also some handmade by Derby visitors. During an interview with WHAS11, Whitehead showed off one crafted from from a Viking helmet into a replica of the Twin Spires. 

For those who prefer to make a fashion statement, rather than a funny one, master milliners are the arbiters of taste. 

Louisville's Ilana Kogan, aka the Hat Doctor, started making hats to pay off student debt while in Kentucky for medical school. 

"I thought I was a fashion expert coming from New York and I've seen it all," she said. "But when I saw the fashion at the Derby I was mesmerized." 

What started as necessity became a passion. Now, the full time radiologist is also one of the Kentucky Derby Museum's featured milliners and chief trend setters

"People really want to show what they have this year," Kogan said of Derby 150 hat choices, "They want to show their personal style, they want to put their best foot forward and have a gorgeous outfit head to toe." 

This year, Kogan said reds and greens are having a moment, as well as shapes that nod to the past and call back tradition. 

"Especially for Derby 150 I think people want the classic look of a wide brim hat," she said.

Tradition is Whitehead's bread and butter. This summer, she has the tall task of documenting the decades in a new exhibit featuring a collection of past Derby ensembles sourced from people's own closets and wardrobes. 

"We're so excited to be celebrating the 150th anniversary of the Kentucky Derby," she said. 

The goal is to tell the story of fashion from 1875 to 2024 and every year in between, Whitehead saying fashion history is really about our shared story -- a story worth remembering. 

"You're sending a message about your individuality, your selfhood, about where we are in history," she said. 

The "See & Be Seen" exhibit is scheduled to open in July of 2024

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