Daily Inspiration: Meet Helen Overfield

Today we’d like to introduce you to Helen Overfield.

Hi Helen, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers.
How “Hats Off by Helen” began.

I have been making Derby hats and fascinators, “unofficially”, for more than 30 years. Helen and her husband, who was in the bourbon industry, entertained out-of-town guests and clients for countless Derby weekends for decades.

Every year, some guests were unprepared for the Derby fashion expectations and arrived sans hats. I began making these women’s hats or lending them one of my own. Enough of these experiences eventually led me to start Hats Off by Helen in 2014. (I realized I was soon going to be an empty nester and needed a creative project.)

At the time, I had three daughters in three different colleges in three different states, and the hats and fascinator “hobby” kept me from missing them. I had so much fun with the hobby turned small business, creating most of the hats and fascinators in the evening or on weekends in my studio as I still had a full-time job as a non-profit executive.

I am now quasi-retire, and my three daughters have graduated and are living back in Louisville, Kentucky They often help with the business, particularly during the Triple Crown spring season of thoroughbred horse racing – the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes, as well as Breeders’ Cup in the Fall, so it has become a family affair.

My hats and fascinators are made primarily with the Kentucky Derby in mind, but have been purchased for home Derby parties, Breeders’ Cup, Preakness, Belmont, Saratoga, Keeneland, Del Mar, Santa Anita, a variety of polo matches, steeplechases, carriage driving and other equestrian events, as well as Mardi Gras luncheons, debutant luncheons, garden parties, teas, and weddings.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It’s been smooth. I began small and grew exponentially each year. I added custom orders to my repertoire, where women can send me their outfits and I custom make a hat or fascinator to coordinate.

Since I am a relatively small business, it was a challenge to meet the demand initially, as I didn’t stock all colors, shapes, and sizes.

Appreciate you sharing that. What else should we know about what you do?
I enjoy the creative process of making hats and fascinators and having women look their best when they attend events. Oftentimes first-time Derby-goers are afraid of wearing a large hat and might be more comfortable starting with a fascinator.

However, once they attend the second largest Derby Party in Denver Colorado, or the actual Kentucky Derby in Louisville, Kentucky and they see the colorful menagerie of styles – they come back the next year, wanting larger and more over-the-top creations. I specialize in unique headwear – all of them are one of a kind, I do not mass-produce, so no one will be wearing the same thing at an event.

All of my creations are titles, bearing the name of what could sound like a thoroughbred racehorse in the paddock or at the track, such as “Paddock Princess,” “Derby Delight,” “Oh Oh Chapeau,” “Fanciful Filly,” “Majestic Main, “Colorful Colt,” etc… In addition, each hat or fascinator comes with two lucky betting numbers and instructions o how to bet a boxed exacta bet. Women will tell me they used the lucky numbers or bet on a horse with a similar name as their hat, and they cashed winning tickets at the racetrack.

My level of customer service sets me apart from others. I regularly text and email with my clients to meet their needs. If a woman is buying a hat or fascinator and I think it is wrong for her outfit, head shape, or skin tone and hair, rather than make the sale, I will suggest another item or make her a different one that will compliment her better.

I have even recommended other milliners or hat shops if I am sold out of a certain style or color. I want her to be happy and look good – not just bring in sales. I also am a self-proclaimed Ambassador of the Kentucky Derby and other equestrian events, and share tips and knowledge that I have learned traveling to them throughout the years.

Can you talk to us a bit about the role of luck?
I suppose luck and faith sort of go hand in hand. I was diagnosed with cancer in December 2022 and am in the middle of chemotherapy. The Hats Off by Helen Business keeps my mind on the “what if’s” and the nasty side effects of cancer and chemotherapy. I get lost in the creative process when working in my studio, and forget that I am “sick.”

I am lucky and thank God every day that it was caught very early and I will beat it. My family and friends have been tremendous support for my illness and my small business, and I am fortunate to have that level of love, kindness, and support.

Pricing:

• $50-$350

Contact Info:

• Website: www.hatsoffbyhelen.com
• Instagram: https://www.instagram.com/hatsoffbyhelen/
• Facebook: https://www.facebook.com/hatsoffbyhelen/
• Other: https://www.etsy.com/SHOP/HATSOFFbyhelen 

Image Credits
Alli Overfield