People

Helen Overfield: “Focus on the hat!”

As you gaze upon the sea of Derby hats this year, chances are you may be admiring one of Helen Overfield’s creations. A longtime craft hobbyist turned successful small-business owner, Helen could not have anticipated the popularity that Hats by Helen has seen. As we look to the 150th running of the Derby this year, business is as brisk as it’s ever been. Fortunately for us, Helen was willing to take a break and share some of her experiences and expertise.

Your work is stunning. Surely you have always had an artistic flair?

My family was really inclined toward the arts. My parents took us to art galleries and shows. I loved painting and drawing as a kid. In my own home, I enjoy design and decoration — wreaths for the front door, window treatments, making pillows. I always loved doing arts and crafts with my kids. But a flair for music? Never. You need me to stay far away from that!

Speaking of your kids, I understand they had a hand in the creation of Hats by Helen?

In many ways, this is a family business. My husband worked in the bourbon industry, and we entertained his guests for three decades. Often, if they came to the area for Derby, they wouldn’t have a hat, or they didn’t realize they needed a different one for each Derby event. I would help them by lending a hat of my own and embellishing it to match their outfits. These were his guests, and we wanted to help them feel a true part of the Derby experience. Soon, family and friends asked me to help with their headwear as well.

It didn’t become a business though until my kids went to college. One of my daughters said, ‘Mom, you should do this on the side. You love it and you’re really good at it.’ I started Hats by Helen in 2014. Those were pretty hectic days because I still had my full-time job, but I really enjoyed creating hats on the weekends. In time, I had more business than I could handle. I retired in 2021 and have been going full-tilt at this since then. It’s so fun!

Is it a fairly seasonal job?

Of course, it’s busiest during the Derby. But, there are equestrian events all year round. You have races like the Breeder’s Cup and the Preakness. There are smaller equestrian events throughout the East and West Coasts. People even order amazing headwear for Mardi Gras. I can tell what area of the country is having an event based on the location of my orders.

What comes first, the hat or the dress?

That’s really a matter of personal preference. Everyone wants a unique piece. You don’t want to look over and see you’re sitting next to someone with the same hat or fascinator. Sometimes you find the outfit first; sometimes it’s the hat. However, think about if it rains and your clothes are covered up. Then, it’s truly all about the hat. So, for me, that’s where I start.

Do you have any specific rules of thumb for us to follow?

I am a brunette and gravitate toward bright, bold, vivid colors. My daughter, who has blond hair, often reminds me that I need to create with pastels as well. One rule I like to follow is that if the dress has a lot of design, the headwear should be fairly monochromatic. If the dress is simple, we can go wild with the hat.

Are some colors more popular than others?

We know that Oaks Day is all about pink, and then you consider the Survivors Parade, and you have even more. I’m trying to stock more pink, fuschia, and magenta to be ready.

I love pink! And, like all of us, I’m deeply moved by the Survivors Parade each year.

Yes, and this year, I am really celebrating. After a cancer diagnosis in December 2022, three surgeries, and three rounds of chemo, this year is quite special. I’ve been in remission for three months. Funny thing: this year was my best ever for hat sales. I was grateful to have this work to take my mind off my own health issues.

I’m so glad you’ll be celebrating along with the other survivors this year! Aside from the obvious joy you get from creating these beautiful pieces, what else inspires you?

My parents told me that I could do anything I set my mind to do. I am pleased that I can show my own daughters that being 66 is not too old to do something new. I also love to help people feel pretty and confident. I want everyone to feel elegant and sophisticated, and I love thinking that they may even be stepping a bit out of their usual comfort zone with the confidence of knowing they look great!

Any last piece of advice for our readers?

Shop early! People are pulling out all the stops this year for Derby 150. Oh, and wear comfortable shoes. No one is looking at your feet. Focus on the hat!

Today's Transitions Spring 2024

By Megan S. Willman | Photos by Melissa Donald