Hats are a well-known tradition in horse racing and a must-have item at events large and small at a race track. 

The go-to gal for the most fashionable hats to see and be seen in is Natalie Sillery, owner of Saratoga Trunk. Over the past 14 years, Sillery has helped dress some of the most fashionable women; however, just this past week, her hats decorated the Winner’s Circle at the Kentucky Derby. 

After receiving a strange phone call from a complete stranger in Mid-April, Sillery found herself driving to Long Island with a car full of hats of all shapes, sizes and colors.

“This gentleman kept mentioning IEAH Stables and said he wanted to show horse-owner’s wives some of my hats, but I didn’t really know what I was getting into,” Sillery said.  “He told me that whenever he sees hats he thinks of Saratoga Trunk and he could guarantee that I’d be showing off my hats to more than 10 ladies who would be attending the Kentucky Derby.”

Sillery’s next step was to make phone calls to her loyal hat designers Nancy Matt and Christine A. Moore to make sure she had a large variety of hats for these ladies to choose from.

“I never duplicate a hat. Once a woman buys a hat, it becomes her own. I wanted to make sure these women had unique styles to complete their look,” she said. 

When she arrived in Garden City, Long Island, the man who greeted her kept mentioning a horse called Big Brown and said that he would be the one to watch. Sillery then found out that IEAH Stables owned Big Brown, and the women who would be buying the hats were the stale owner’s wives. 

“It was a whirlwind business meeting.  As soon as I got there, women started filing into the office to check out the hats.  I sold 13 by the time I left,” she said. 

Come the day of the Kentucky Derby, the women from IEAH Stables lined the fence in hats from Le Beau Chapeau and Mona The Mad Hatter, the stores the designers own, Sillery said.

After Big Brown won the race, Sillery saw her hats being photographed in the Winner’s Circle.

“I was so proud and so excited for Nancy Matt and Christine A. Moore. There truly is a hat for every kind of woman, and you could see it right there,” she said. 

Sillery has been in the business for 14 years and said that her hats have always been a hot seller.

“It’s just a race track tradition. They are fashionable and functional. I’d put money on the fact that some women buy their hat and base the rest of their outfit around it,” she said. “They are the best bet for women.”

As a “thank-you,” Sillery is sending an enormous brown hat called “Fortissimo” to the office where she met the owners of Big Brown. 

“I thought it was very fitting to send them a big brown hat,” she said. “I ordered it especially for their horse.”

Sillery said she learned a lesson through this experience. 

“If anyone calls and offers me an exciting opportunity like this one, I know not to think twice. You never know what is going to come of it,” she said.