Meet Helen Overfield | Kentucky Derby Hat Designer

We had the good fortune of connecting with Helen Overfield and we’ve shared our conversation below.

Hi Helen, is there something that you feel is most responsible for your success?
Being relevant contributes to success. Having attended the Kentucky Derby since 1987, I’ve seen and made and worn many hats. When women are looking for a hat to wear to the races – they know one made in Louisville, Kentucky – “home of the fastest 2 minutes in sports” will fit the bill. A “Hats Off” creation will make an entrance. I initially began with hats, however the European influence of the fascinator was recognized, and I branched out. Fascinators have proven as popular as the hats. It’s important to know what your target audience wants and needs.

Alright, so let’s move onto what keeps you busy professionally?
Professionally, for the past 2 decades, I have been an Executive Director of many non-profit organizations. I also did a lot of volunteer work and served on several non – profit boards in the community. Learning from other business owners and professionals has been ongoing in terms of professional development. One thing that sets me apart from others is my commitment to creating unique, one of a kind hats and fascinators. No two items are exactly alike, as I don’t mass produce them like many others do. I can customize and create a piece to match a person’s outfit. Oftentimes, a person sees a hat or fascinator on my web site and wants to add a color to match their outfit. As a small business, I work with them and give them a high level of customer service, which is so is valuable. I have had many clients attend the Kentucky Derby for the first time and they want a hat made in Kentucky, not from a department store. I share guidelines for traveling with a hat and also do’s and don’t for wearing hats and fascinators, as well as “hot tips” for navigating Louisville and Churchill Downs. I have many repeat clients. I began with the idea of creating items for the storied Kentucky Derby, always the first Saturday in May. However, 90% of my business is out of state – women coming into Kentucky that kind find an embellished hat or fascinator in their state. I have expanded the business to fall and winter hats to include the Breeders’ Cup in November. In addition, people purchase them for polo matches, steeplechases, carriage driving, luncheons, garden parties, Derby themed parties, weddings, and other equestrian events, I’ve learned from my customers the types of hats and fascinators they want and have adapted and grown creatively. A few unique aspects – each hat or fascinator is named with a title that sounds like a thoroughbred horse such as “Trainer’s Tip”, “Oh Oh Chapeau”, “Bourbon Babe”, “Sure Bet.” Each creation comes with two lucky numbers and instructions to bet an exacta. Many clients call me afterwards and tell me their lucky numbers won, or a horse running in a race sounded like the hat they were wearing. It adds tot he horseracing experience.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
( I am assuming you meant in Denver?)

Louisville has so many fun places – restaurants on the river, museums, galleries, shops, boutiques, and eateries downtown, in Nulu, an artsy area near downtown, Frankfort Avenue and Bardstown Rd.
Museums: Speed Museum, Kentucky Museum of Art and Craft, Kentucky Derby Museum, Muhammad Ali Museum, Louisville Slugger Museum
Tours: Bourbon Trail or Urban Bourbon, Belle of Louisville boat ride, CQ Princess boat ride, Thunder Over Louisville ( USA’s largest longest fireworks display 2 weeks before the Kentucky Derby – the kick off to the KY Derby Festival.)
Restaurants: Vincenzo’s, Mesh, Volare, Varanese, River House, Captain’s Quarters, The Pine Room, Guacamole,

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
My family supported and encouraged me to turn a creative hobby into a business. My husband was in the bourbon industry and we attended the Kentucky Derby, and the Triple Crown of racing (Derby, Preakness in Maryland, and Belmont in NY.) I embellished hats for friends and clients. When my daughters went away to college, they encouraged me to do it as a small business. They helped design a web site and coordinated photography, helped create a studio, and even assisted with shipping. So… a shout out to my 3 daughters and husband is in order.

Website: hatsoffbyhelen.com

Instagram: Hats Off By Helen

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