Photo courtesy of Kentucky Derby Museum
Jenny Pfanenstiel: Master Milliner
by Gioia Patton/Arts Insider
“A hat can not only change your day, but it can also change your life!” – Jenny Pfanenstiel
6x Featured Milliner of the Kentucky Derby®
When this Arts Insider’s interview with Master Milliner Jenny Pfanenstiel comes out, the 2025 Kentucky Derby will be a mere six weeks away. Pfanenstiel, owner of Formé Millinery in Louisville, Judith M Millinery Supply in La Grange, and The Hat Shoppe in Louisville, is a six-time Featured Milliner of the Kentucky Derby® at Churchill Downs, the Official Milliner of the Kentucky Derby Museum, and a nine-time Featured Milliner of Keeneland Racetrack. Pfanenstiel is also one of five talented female milliners selected by the Kentucky Derby Museum as KDM’s Featured Milliners for the 2025 season, and whose designs will make up the Kentucky Derby Hat Show on March 23rd at the Kentucky Derby Museum.
To date, Pfanenstiel’s work has been showcased in over 500 publications, radio, and television appearances and in numerous millinery events worldwide. Her first book, The Making of a Milliner, with Dover Publications was published in 2015. In 2019, she was honored as a Tory Burch Fellow, recognizing her as a top female entrepreneur. The Louisville-based Pfanenstiel now serves as a mentor for aspiring business owners, sharing her expertise nationally. Currently working on her second “How to” book, the Monument, CO. native regularly leads workshops across the globe to preserve and advance the art of millinery.
With the Kentucky Derby® only six weeks away still in mind, the Arts Insider’s initial question to Pfanenstiel is to inquire just how long it takes her to create a hat?
“Creating a hat can take anywhere from three days to three weeks, starting with the time-honored technique of blocking—wetting and steaming the material to mold it over custom blocks,” Pfanenstiel begins. “I source only the finest materials from England, France, and Australia, ensuring each hat is crafted with exceptional quality. Once the material is steamed, shaped, smoothed, and secured, it goes through a drying process before I cut, hand-sew, and assemble the hat. A sweatband and wire are added for comfort and structure, ensuring a perfect fit. Every embellishment is handmade, from sculpted horse hair designs to delicate feather flowers, offering endless possibilities for creativity and customization. I work closely with my clients to design hats for all genders, occasions, and seasons. The process begins with a head measurement, followed by choosing materials, colors, and shapes that best complement each individual’s style,” she adds. “The result? A one-of-a-kind hat that fits flawlessly and reflects their personality.”
It was while in college studying at the Art Institute of Colorado (where she earned a Fashion Degree), that the then Jenny Gerst made her very first hat. She recalls “I would make hats to complement my collections. At the time, I didn’t really know what I was doing, but that’s when I first started dabbling in hat making.”
Atlhough the creation of that first hat may not have occurred until she was college-age, a particular talent for design of any kind initially revealed itself when she was just a little girl.
“I started sewing at 5 years old when my mother taught me how to cross stitch. This eventually led me to design school, but it wasn’t until I traveled to Australia to learn traditional hat making techniques, which date back centuries, that the light bulb finally went off. Something inside me said, ‘This is what you’re meant to do.’ In design school, I created fashion through draping, a more sculptural method of design, similar to how I now create hats. Since I already knew how to hand sew, the hat-making technique came naturally to me.”
As to whether or not her parents encouraged this pursuit when it came time to apply for colleges, she admits “When I started looking at colleges, they probably would have preferred I pursue a different profession, worried I might end up as a ‘starving artist.’ However, after 17 years of making hats, building 4 hat companies, and opening 3 retail stores, they now see that I’ve created something truly special.”
Pfanenstiel says she can trace back to her 2014 relocation from Chicago to Kentucky to when she could finally label her millinery career “a success.”
Seventeen years ago she had begun making hats as a hobby in her basement in Chicago, “never imagining it would turn into a career,” she says. “However, it wasn’t until I moved to Kentucky in 2014 that I truly felt I could elevate my business. That’s when I took the leap and opened my first retail store. Moving my business out of my home and into its own space marked the beginning of a new chapter, turning my passion into a legitimate, thriving business.”
Why the move to Louisville in the first place?
“My goal was to expand my hat business and take it to the next level by opening a retail storefront,” she explains. “At the same time, my husband and I were thinking about starting a family, and we knew we didn’t want to raise our child in a big city like Chicago, where we had lived before. Moving to Kentucky offered the perfect opportunity to both grow my business and create the kind of environment we wanted for our family.”
When the Arts Insider then enthuses (that) one of her favorite things about watching films from the 1930s & 40s is that everyone wears hats, including the *men, (*another unfortunate bygone era), she is delighted to learn (that) Pfanenstiel picks that same era.
“I’ve always been fond of the style and craftsmanship from the 30s and 40s. I consider myself an old soul, and I surround myself with vintage items, many of which fill my hat shop. These vintage pieces are a constant source of inspiration for me. I often think about the people who crafted a trim 70 years ago that I’m now using on a hat, or the hands that shaped a hat on one of my vintage blocks. Even the hundreds of pins that go in and out of my antique pincushion make me wonder – what were they creating back then, and who was it for?” she muses.
The price range of the hats in Pfanenstiel’s shops range from $450-$3000+, and about 40% of her clients are gentlemen.
Her most difficult professional challenge to date, she admits, is “knowing when to ask for help- which has always been a challenge for me. When you first start out in your profession, you wear all the hats (pun intended!) and do everything yourself. But there came a point when I had to delegate some of my work to keep things moving forward. Letting go of control was tough by trusting others to block, sew hats, and oversee projects to the standards I set was a big hurdle. It took time to find the right people, but I realized that in order to grow, delegation was essential. After all, even Oprah doesn’t run every aspect of her business. I knew I couldn’t do it all myself forever.”
Pfanenstiel is then informed (that) this writer wears some form of a hat 12 months of the year, which explains why she wonders if at any point during Pfanenstiel’s lectures and TV appearances if the milliner tries to convince people (that) the love of hats should span more time than just Derby week?
“It’s not necessarily about convincing someone to wear a hat outside of Derby week but about showing them what a hat can do,” she replies. “As I always say, a hat can not only change your day, but it can also change your life. Yes, most people understand that a hat protects you from the sun, but a hat should be viewed like any other accessory—like a bag, shoes, or jewelry. It completes your look. My goal is to keep this craft alive. A hat often becomes a conversation starter, creating the perfect statement and setting the stage for yet another memorable life moment. When I reflect on some of the most important events in my life, I often associate those memories with the hat I wore that day. Hats don’t just complete your style; they create a wearable journal of life’s adventures.”
Finally, and as Pfanenstiel’s interview is wrapping up, it suddenly occurs to the Arts Insider to ask if she is the first milliner in her family? Funny enough, as it turns out, Pfanenstiel’s response is the perfect close to her interview.
She exclaims “I found out about 4 years into making hats that my great grandmother was a milliner. It was in my blood, and I didn’t even know it!”
