Hat Trick: An Interview with Derby Hat ‘Artist’ Helen Overfield

Spring race season is just around the corner. Whatcha gonna wear? We talk to the proprietor of Hats Off! by Helen about the the inspiration behind her one-of-a-kind hats and fascinators.

Helen Overfield lives in the heart of fancy hat country: Louisville, Kentucky. She knows the tradition well, having attended the Kentucky Oaks and Derby for over 25 years. She has been creating her unique hats and fascinators for decades for friends, family and select clients with her Hats Off! business. Helen is a busy lady this time of the year but kindly took the time to speak with Horse Nation about her craft.

How long have you been making hats and fascinators? How did you get started?

I have been making hats for over 20 years. It began on a personal note when I couldn’t find the perfect hat to wear with my outfit for the Kentucky Derby, so I found a plain hat and made one to match. Later for other events, like the Preakness, Belmont or steeplechases, I would find a hat but felt it needed embellishing. (So many in the stores seemed so plain and ordinary.) At the Kentucky Derby, hats tend to be more colorful, making a real statement.

I love to design and create. Friends and family asked if I could help them with their Kentucky Derby ensembles. Years ago we had many business clients come in town for the Kentucky Derby — some had never been to Churchill Downs. They didn’t realize wearing a hat was de rigeur for women at the track. So, in keeping with “southern hospitality and corporate entertaining,” I asked them what color they were wearing and created hats for them. People kept telling me over the years, “you should sell these; they are so unique and stunning!”

The actual Hats Off! business came a year and half ago, when I realized I was going to be an empty-nester in a year and needed a project. I now have three daughters in three different colleges in three different states, and the hats and fascinators keep me from missing them! I am having so much fun with it. They are made with the Kentucky Derby in mind but have been purchased for steeplechases, polo matches and other equestrian events, as well as Mardi Gras luncheons, teas and weddings.

Your work is one of a kind. What inspires your creations?

  Everything inspires me: being at the racetrack, shopping, being outdoors or in art galleries — seeing colors and design. When I travel and experience new things it inspires me to be creative. Each hat or fascinator is unique, so no one will be at an event wearing the same headwear.

About how many hats do you make each year? What is prime hat season?

I make anywhere form 200 to 250 each year, but the business is growing, so I will likely go over 300 this year. Prime hat season for the Kentucky Derby is March and April, though I sell year round.

Do you do commissions? What does that process look like, and how long does it take to go from idea to reality?

I don’t do as much commissioned custom work anymore, though that’s how I got started. I just don’t carry enough inventories of materials — colors of plain hats and embellishments such as flowers, feathers and ribbon for that. My hats are moderately priced, and custom hats would nearly double the cost. I have a variety of styles and colors that people can choose from. I often refurbish a hat for a client. If a person already has the hat and the materials, but needs design assistance, I can help with that. Most women I know buy their hat and then their dress — it’s easier! In Kentucky we say “It’s ALL about the hat!”

Your hats and fascinators are worn all over the world. Have you ever had any celebrity clients?

I haven’t had any celebrities that I know of yet. Last year, the wife of the jockey that came in second place at the Kentucky Derby was wearing a Hats Off! hat. She looked lovely, and we both joked that we almost made it to the winner’s circle. I have been shipping all over the United States and have had interest from so many other countries and continents. It’s so fascinating as there are so many equestrian events and occasions for women to wear hats all over the world.

Is the Kate Middleton fascinator trend still raging on?  

Yes, Kate Middleton has made the fascinator even more fashionable. Some people, if a bit shy about headwear, will try a fascinator and then graduate to a hat. I encourage women to wear what makes them happy and be comfortable with their look, whether they want elegant and classy or ostentatious and flamboyant. Some people just look better in a wide brimmed hat, others a smaller style. It just depends on the person’s stature, face shape, their skin tones, hairstyle, hair color and even personality. Many women are catching onto the appeal of fascinators at the racetrack and at weddings and cocktail events.

Hat trends: What’s in? What’s out?

What’s in? Feathers, larger flowers, bold colors, unique textures and interesting design are important. We’re getting away from the “matchy-matchy” look, and we are seeing hats and fascinators complement or accent the outfit. The monochromatic look is still popular but that pop of color that coordinates is a great look for accessorizing one’s outfit. Larger brimmed hats are becoming more popular, and so are fascinators and hatinators (part hat/part fascinator.)

What’s out? Wearing your hat balanced on the back of your head (that was never really “in” but it is surprising how many people wear a hat incorrectly). A hat’s brim should be worn in the middle of one’s forehead.

I assume you’ve been to a million races yourself. What’s the best/your favorite race you’ve ever seen live?

Yes, I have been to the Triple Crown, and many steeplechases and polo matches. I’d like to go to the Royal Ascot someday. My favorite race was a Kentucky Derby many years ago — the payoff was very large on some small bets I placed; Churchill Downs had me fill out IRS papers and later sent me a 1099 form!

Your hats have a fun, signature, race-inspired twist. Tell us about that.

Each unique hat has a special name that resembles a horse one might find in the paddock, the barn or at the racetrack, for example: “Bluegrass Baby,” “On Millionaire’s Row,” “All Saddled Up” and “At the Starting Gate.” They also come with two lucky betting numbers to use at the racetrack. Last year a friend won an exacta betting them!

Anything advice for readers ?

Don’t be afraid to try something new. Wear your hat with confidence. I tell my clients that the best accessory for a hat is a smile! If you ever watch women try on a hat or fascinator and look in the mirror, they always smile. Hats make people happy!

Many thanks to Helen for sharing! You will be taking private appointments between now and Derby for those that haven’t yet found the perfect hat and can be reached at (502)553-4342. If you live in the Louisville area, look for her hats at semi-private trunk shows and in various boutiques around town, or check out her work online via the Hats Off by Helen Etsy shop and Facebook page.

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