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Helen Overfield has been making Derby hats, unofficially, for more than 25 years. As a corporate wife, Helen helped her husband entertain out-of-town guests and clients for countless Derby weekends. And every year, there were guests who were unprepared for the Derby fashion expectations and arrived sans hats. Helen unfailingly came to the rescue, making these ladies hats or lending them one of her own. Enough of these experiences eventually led her to start a legitimate business, and she opened Hats Off by Helen a year and a half ago. Today, we welcome Helen as our FACES of Louisville feature. Welcome, Helen!

Helen Overfield of Hats by Helen-

Helen Overfield of Hats Off by Helen

Do you remember the first hat you made?

Yes. I couldn’t find a hat that coordinated with the outfit I was wearing to the Kentucky Derby, so I decided to make one that did. That was more than 20 years ago, and I still have it!

When did you start making hats, and when did you realize you could make a living by doing this?

It began on a personal note when I couldn’t find the perfect hat, or if I found a hat, I felt it needed embellishing, so I added to it. I have always loved to design and create. Friends and family began asking if I could help them with their Kentucky Derby ensembles. Also, years ago, we had many business clients come in town for the Derby. Some had never been to Churchill Downs, and they didn’t realize wearing a hat was de rigeur (“required”) 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.

Helen Overfield of Hats by Helen-latest trends in Derby Hats

Tell us the difference between what you do and what a milliner does.

A milliner actually makes the hats, beginning with sinamay straw or other materials, and uses various hat forms to fabricate the hat. It’s very time consuming, and those hats are often far more expensive than the average consumer can afford. My price points are $50-$250, with the average hat costing $125.

I make fascinators, but I purchase “naked” hats and then design the embellishments to create the perfect style. I use a variety of textiles, like taffeta ribbon, silk, exotic feathers, silk flowers, sinamay, etc. Each piece is a one-of-a-kind creation, so no one will be at an event wearing the same thing purchased from a store.

Also, each hat has a special name that resembles a horse one might find in the paddock, for example: Superfecta Sweetie, On Millionaire’s Row, All Saddled Up and Derby Diva. They also come with two lucky betting numbers to use at the racetrack. Last year, a friend won an exacta betting them!

Where can we buy your hats?

The Kentucky Derby Museum Gift Shop, and several boutiques in Louisville will be carrying them. I have been approached by several websites that do equestrian e-commerce. The easiest places to see colorful photos are on my Etsy Shop, hatsoffbyhelen or on my Facebook page, Hats Off by Helen.

Hat? Fascinator? How do you recommend what is right for each woman?

For me, it’s a hat, but it’s really personal preference. 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. Do they want elegant and classy, or ostentatious and flamboyant? Some people just look better in a wide-brimmed hat, others in a smaller style. It just depends on the person’s stature, face shape, their skin tones, hairstyle, hair color and even personality.

Helen Overfield of Hats by Helen-Helen wears blue hat with peacock feathers

Any advice on how to wear a hat? Or a fascinator?

Wear them with confidence and good posture (our mothers were correct!). I personally prefer hats that make a statement, versus the subtle and sedate, but I make something for everyone from modest to over the top. Please don’t wear your hat balanced on the back of your head. The brim should be on your forehead.

What are the trends you are seeing for this year?

Bold and big. Larger flowers. Feathers. Unique textures and interesting design. Fashion is getting away from the matchy-matchy look, and we are seeing headwear complement or accent the outfit. The monochromatic look is popular, but so is that “pop” of color.

Hat before the dress? Or vice versa?

Hat first! Most definitely. If you have a great hat you love, it’s much easier to find a solid or neutral dress or suit. In Louisville, on the first Saturday in May, it’s ALL about the hat! People will rarely remember what you wore, but they will remember your hat! I have clients who tell me they accessorize and get dressed around their Hats Off! hat or fascinator.

Helen Overfield of Hats by Helen-Helen and her creations

Who are your mentors and what advice do you treasure?

My parents. They are both in heaven looking down on me with a smile. Dad loved art, to create and invent. Mom had a great eye for presentation and design and taught me to sew. As a child I remember going to art galleries and museums with them, absorbing it all. Their sage advice: “You can do anything you want to, as long as you set your mind to it.”

What does a typical day or week like for you?

Each day is different, depending upon the time of year. I buy items online or when I travel. I could spend an entire Saturday upstairs in my studio designing, sewing, gluing and creating. The hours float by, and it doesn’t feel like work. I upload pictures and answer email in the evening while watching the news.  No one day is the same. I am most creative in the evenings and Saturday mornings.

If you were not in your current job, what would you secretly love to do?

In my next life, I’d run a pediatric clinic in an underserved area of the United States or a third world country. In addition to healthcare, tie in the arts and education for the children and their families.

Helen Overfield of Hats by Helen-pink hat for Derby

What is something people would be surprised to know about you?

I love to zipline and snorkel. I also have an incredible memory for minutiae and trivia, so games or shows like “Jeopardy,”  Trivial Pursuit and Trivia Crack come easy.

Fill in the blank. You’ll never see me without my:


Favorite thing to do in Louisville:

Besides cashing a winning ticket while wearing a hat at the track? Be anywhere with my family: a show, movie, restaurant, the track, pool, park, museum, gallery, store, sporting event, even just hanging at home.

Tell us some of your favorite local restaurants.

Lilly’s, Porcini’s, Village Anchor, Vincenzo’s

Helen Overfield of Hats by Helen-Helen works in her office full of feathers and flowers

Lightning round! Give us your:

  • Candy or junk food splurge:  Heath Bar. Girl Scout Thin Mint cookies. Anything chocolate!
  • Guilty pleasure song: “Fur Elise” (Beethoven). I could listen to it over and over and over and over, but it’s not really a song is it?
  • Tearjerker movie pick: Gone With the Wind
  • Standby nail polish color: Magenta
  • Favorite cocktail: In May, a Mint Julep of course! I enjoy wine, but my cocktail? Cosmopolitan or lemon drop martini
  • Cartoon alter-ego: Disney’s Ariel the Mermaid. I love to swim and love to try and explore new things.

Need a Derby hat?  You can reach Helen Overfield at (502) 553-4342 or by email at [email protected].

As always, much gratitude to our FACES photographer, Adele Reding, for her fantastic work. Visit her website at

Edition Mar 2015

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