Everyone knows that hats adorn throngs of women during Kentucky’s horse racing season, especially when the Derby rolls around.
But who makes all these masterpieces? One of the leading hat makers is Louisville-based Helen Overfield, who got into the business by accident.
“I have been making hats for the Kentucky Derby for over two decades, mainly for myself and for my friends,” she said. “It began when I couldn’t find a hat to match my own ensemble, so I bought a relatively plain hat and embellished it.”
And now, she’s extended the results of her creative passion to hundreds of other women through her enterprise Hats Off by Helen. Hats are big business, and Overfield stays busy.
For nearly 30 years, Overfield has worn hats herself—to the Oaks, Derby, Breeders’ Cup, Keeneland, Preakness, Belmont, steeplechase races and more.
“I have always had a keen eye for design and a strong interest in art and craft,” said Overfield, who works full time as the executive director of the Leukemia and Lymphoma Society of Kentucky and Southern Indiana. “My husband was in the bourbon industry for many years, and we entertained corporate clients Derby weekend. At the time, many of the women coming to their first Kentucky Derby didn’t realize everyone wears a hat at Churchill Downs. They were in Louisville for the weekend, and I would loan them one of mine. I had probably five dozen at home.”
When their three daughters went off to college, leaving the Overfields as empty nesters, they created a studio for hat creation.
“I wanted something to do to fill the void of all the activities … the field hockey games, lacrosse games, swim meets,” Overfield said. “So I decided to begin selling the hats as a hobby three years ago, and then it grew into a business.”
Even the daughters are involved, with one creating a website, another modeling hats, and the third taking photos.
Overfield hopes to make women feel more self-assured.
“I feel more complete and confident with a hat on at equestrian events,” she said. “I gravitate to the larger brimmed hats, as do most women in the South. I have never worn a fascinator to the track.”
She added that many people have begun requesting fascinators, influenced largely by Catherine, Duchess of Cambridge (the former Kate Middleton), and their popularity is rising. Overfield also makes hybrid “hatinators.” No matter the style, she loves the effect on a woman’s entire persona.
“When a woman puts a hat on and looks in the mirror, she smiles,” Overfield said. “I think it makes a woman feel more confident and more stylish. Our society has become so casual—it’s a time when a woman can get a bit out of her comfort zone and have a stylish attitude, whether it is to feel elegant, outlandish, or just completely put together.”
Now entering her third year in business, Overfield runs a booming Etsy shop (etsy.com/shop/hatsoffbyhelen). Most of her creations sold through Etsy or her main site, hatsoffbyhelen.com, are purchased by out-of-state customers. In her first year, she had 28,000 website views from 45 different countries.
To fill her hundreds of orders, Overfield has a large studio upstairs in her home. She said it’s full of hats, feathers, flowers and ribbon, and it’s fitted out to specifically suit her hat business. In that space, Overfield creates and sells hats all year long. Women also wear hats to other events, such as luncheons, weddings and garden parties.
“The Triple Crown is my busiest season,” she said. “I create the hats and fascinators in the evening. It is relaxing to me to create after a day of work … sort of a left brain, right brain thing. On the weekend, I box and ship.”
Her busiest months are March and April, and she said the neighborhood post office knows she’s coming with many boxes on Saturday mornings.
“I gear up for it all year,” she said. “For example, I can make every shade of pink hat all year long, and they will sell out before Oaks day. The Friday before Derby, the fillies run [in the Kentucky Oaks], and many women wear pink.”
Custom orders are fun for her. Women send her photos of their dresses, and she then creates a coordinating headpiece.
“I often send the photos to my daughters, and they help pick one out in stock or suggest styles and colors to make,” Overfield said. “I am very organized, so the only time it is problematic to fill an order is when someone waits until the last minute. But I have shipped overnight before and have even shipped the hat to their hotel. One woman flew into Louisville, picked up the hat from my front porch, and then drove out to Churchill Downs.”
Pieces ordered from Hats Off by Helen range from $50 to $250.
“At the Kentucky Derby, it’s all about the hat,” she said. “However, when I began, I wanted to make sure most of my price points were affordable to the average Derby consumer. The average cost of most hats is $150. Not everyone attending horse races can spend $500-plus on a hat.”
However, she said, women still shouldn’t skimp.
“No one will remember the shoes you wore or even the dress or earrings,” she noted. “But they will certainly remember your hat. I want women to have a fun, memorable experience. I tell them that the best accessory to wear with a hat is a smile.”
Creating so many hats seems like it would be challenging at times, but Overfield has a system that she adheres to in her hat making.
“Saturday mornings, it’s a few cups of coffee,” she said. “In the evenings, it’s wine. Maybe that’s when the more outlandish hats are created. When I am in my ‘hat-making zone,’ I get lost for hours. I don’t even realize that much time has passed. Sometimes, I watch a movie, but I work best in quiet—no music to distract me.”
She gets inspiration from people watching and keeping an eye on style trends.
“My hats tend to be conservative with a bit of flair,” she noted. “Each one is unique—I never replicate the hat—they are all one of a kind. They even have their own names, which often resemble an announcer calling the race at a racetrack.”
For example, her hats have been called Legacy Winner, Pink in the Paddock and Furlong Fancy. In addition to their names, each hat and fascinator comes with two lucky numbers and instructions for beginners on how to bet an exacta.
Overfield quipped that she feels like her hats are her “babies” and is a little sad to box them up and ship them off.
“There are about 50 to 100 hats that I wish I would have kept myself,” she said.
The artist gets support from her husband, John, whom she said most likes the wide-brimmed sinamay hats with lots of color.
“He will tell me, ‘This one will sell quickly on your website,’ ” she said. “And he’s usually right.
“His input is in bouncing around marketing ideas and streamlining business ideas. That’s his forté, and he’s great at folding my shipping boxes when I am flooded with orders.”
As a child, Overfield always had an artistic side.
“My parents used to take me to art shows and art galleries as a kid,” she said. “I have always had an interest in art, creating and crafts. I enjoy design, painting, sewing and so on … I like the process as much as the product.”
Still, she’s passionate about her job at the Leukemia and Lymphoma Society of Kentucky and Southern Indiana and is not ready to leave it to make hats full time.
“I donate many hats to various causes for silent auctions,” she said. “Hats Off by Helen has grown to the point of almost a full-time business, but as my daughters graduate, I will pass on some of the business to them. For me, the creativity is the most fun, and the marketing and public relations and business side of it is what they enjoy.”
Overfield regularly has more boutiques and e-commerce sites requesting her hats, but keeping the creations handmade and one-of-kind is her priority. Heaven forbid two women show up at an event wearing matching hats. A hat by Helen will be a standout.